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æÇÍÏ ÑÔÊ
ÇíÇä äÇãå ˜ÇÑÔäÇÓí ÇÑÔÏ M. Sc.
ÑÇíÔ: Ôíãí Âáí
ÚäæÇä ÊÍÞíÞ:
ÓäÊÒ ãÔÊÞÇÊ íÑÇäæíÑÇäåÇ
ÇÓÊÇÏ ÑÇåäãÇ:
ϘÊÑ ÍÓä ˜ÝÇíÊí
ÇÓÊÇÏ ãÔÇæÑ:
ϘÊÑ ÍÓíä ÝáÇÍ ÈÇÞÑ ÔíÏÇíí
äÇÑÔ:
ãåÊÇÈ æËæÞí ÑÇÏ
ÒãÓÊÇä 1392
ÊÞÏíÑ æ ÊÔ˜Ñ
ÈÇ ÊÔ˜Ñ æ ӁÇÓ ÝÑÇæÇä ÇÒ ÑåäãæÏåÇ æ ÒÍãÇÊ Èí ÔÇÆÈå ÇÓÊÇÏ ãÍÊÑã ÌäÇÈ ÂÞÇí ϘÊÑ ˜ÝÇíÊí æ ÌäÇÈ ÂÞÇí ϘÊÑ ÝáÇÍ ˜å ÏÑ ãÑÇÍá ãÎÊáÝ ÇäÌÇã Çíä ÇíÇä äÇãå ÑÇåäãÇí ÇíäÌÇäÈ ÈæÏäÏ æ ÇÒ åí ˜æÔÔí ÏÑ ÌåÊ ÇÑÊÞÇÁ ˜íÝí Çíä ŽæåÔ ÏÑíÛ äæÑÒíÏäÏ.
ÊÞÏíã Èå ÑæÍ ÏÑã
Èå ÇÓ åãå ÒÍãʝåÇíí ˜å ÈÑÇíã ˜ÔíÏ.
æ ÊÞÏíã Èå åãÓÑ æ ÝÑÒäÏÇäã
ÝåÑÓÊ ãØÇáÈ
ÚäæÇä ÕÝÍå
˜íÏå ÝÇÑÓí Í
ÝÕá Çæá: ãÞÏãå æ ÊÆæÑí
1-1 ãÞÏãå2
1-2- ˜æãÇÑíä2
1-2-1- æǘäÔåÇí ˜æãÇÑíä4
1-2-2-1- ǘÓÇíÔ4
1-2-2-2- ˜ÇåÔ4
1-2-2-3- åíÏÑæáíÒ5
1-2-2-4- åÇáæŽä ÏÇÑ ÔÏä ˜æãÇÑíä5
1-2-2-5- äíÊÑæÏÇÑ ÔÏä ˜æãÇÑíä6
1-2-2- Êåíå ˜æãÇÑíä6
1-2-3- ˜ÇÑÈÑÏ 4- åíÏÑæ˜Óí ˜æãÇÑíä ÏÑ ÓäÊÒ ÊјíÈÇÊ Âáí7
1-2-3-1- ÓäÊÒ ÈíÓ ˜æãÇÑíä7
1-2-3-2- ÓäÊÒ ãÔÊÞÇÊ íÑÇäæíÑÇäåÇ9
ÝÕá Ïæã: ÈÍË æ äÊíÌå íÑí
2-1- åÏÝ ÊÍÞíÞ11
2-2- ÈÍË æ ÈÑÑÓí11
2-2-1- ã˜ÇäíÓã æǘäÔ15
2-2-2- ÈÑÑÓí ÚæÇãá ãÄËÑ ÈÑ æǘäÔ16
2-2-2-1- ÇËÑ ÏãÇ16
2-2-2-2- ÇËÑ ˜ÇÊÇáíҐÑ16
2-2-3- ÓäÊÒ ãÔÊÞÇÊ ÌÏíÏ17
2-3- äÊíÌå íÑí18
ÝÕá Óæã: ÈÎÔ ÊÌÑÈí
3-1- ÈÎÔ ÊÌÑÈí20
3-1-1- ÎÕæÕíÇÊ 4- åíÏÑæ˜Óí ˜æãÇÑíä20
3-1-2- ÎÕæÕíÇÊ ÓÏíã Ïí Ýäíá Âãíä- 4- ÓæáÝæäÇÊ20
3-1-3- ÏÓÊæÑ ˜ÇÑ Úãæãí ÓäÊÒ íÑÇäæíÑÇäåÇ21
3- 2-ÈÑÑÓí ÏÇÏååÇí ØíÝí22
3-2-1- ÊјíÈ 7-(3- ÈÑãæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí
Çæä (a3)22
3-2-2- ÊјíÈ 7-(4- ˜áÑæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä 6¡8-Ïí
Çæä (b3)23
3-2-3- ÊјíÈ 7-(4- ÈÑãæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-6¡8-Ïí
Çæä (c3)24
3-2-4- ÊјíÈ 7-(3- äíÊÑæÝäíá)- H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-6¡8-Ïí
Çæä (d3)25
3-2-5- ÊјíÈ 7-(3- ˜áÑæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-6¡8-Ïí
Çæä (e3)26
3-2-6- ÊјíÈ 7-(2- ˜áÑæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-6¡8-Ïí
Çæä (f3)27
3-2-7- ÊјíÈ 7-(2- äíÊÑæÝäíá)- H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-6¡8-Ïí
Çæä (g3)28
3-2-8- ÊјíÈ 7-(4- ãÊæ˜ÓíÝäíá)- H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ[3¡4- b:´3¡ ´4-e] íÑÇä-6¡8-Ïí
Çæä (h3)29
3-2-9- ÊјíÈ 7-(4- Ïí ãÊíá Âãæäíæã Ýäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e]
íÑÇä-6¡8-Ïí Çæä (i3)30
3-2-10- ÊјíÈ 7-(Ýäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí Çæä
(j3)31
ÝÕá åÇÑã: ØíÝ åÇ
4-1- ØíݝåÇí IR¡ 1H NMR¡ 13C NMR34
4-1-1- ØíÝ IR ÊјíÈ 7-(3- ÈÑãæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-
6¡8-Ïí Çæä (a3)34
4-1-2- ØíÝ 1H NMR ÊјíÈ a335
4-1-3- ØíÝ 13C NMR ÊјíÈ a337
4-1-4- ØíÝ IR ÊјíÈ 7-(4- ˜áÑæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-
6¡8-Ïí Çæä (b3)40
4-1-5- ØíÝ 1H NMR ÊјíÈ b341
4-1-6- ØíÝ 13C NMR ÊјíÈ b343
4-1-7- ØíÝ IR ÊјíÈ 7-(4- ÈÑãæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-
6¡8-Ïí Çæä (c3)46
4-1-8- ØíÝ 1H NMR ÊјíÈ c347
4-1-9- ØíÝ 13C NMR ÊјíÈ c349
4-1-10- ØíÝ IR ÊјíÈ 7-(3- äíÊÑæÝäíá)- H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4-b:´3¡ ´4-e] íÑÇä-
6¡8-Ïí Çæä (d3)50
4-1-11- ØíÝ 1H NMR ÊјíÈ d352
4-1-12- ØíÝ 13C NMR ÊјíÈ d355
4-1-13- ØíÝ IR ÊјíÈ 7-(3- ˜áÑæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-
6¡8-Ïí Çæä (e3)58
4-1-14- ØíÝ IR ÊјíÈ 7-(2- ˜áÑæÝäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4-e] íÑÇä-
6¡8-Ïí Çæä (f3) 60
4-1-15- ØíÝ IR ÊјíÈ 7-(2- äíÊÑæÝäíá)- H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡ ´4 -e] íÑÇä-
6¡8-Ïí Çæä (g3)62
4-1-16- ØíÝ IR ÊјíÈ 7-(4- ãÊæ˜ÓíÝäíá)- H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ[3¡4- b:´3¡´4-e]
íÑÇä-6¡8-Ïí Çæä (h3)64
3-2-17- ØíÝ IR ÊјíÈ 7-(4- Ïí ãÊíá Âãæäíæã Ýäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡
´4-e] íÑÇä-6¡8-Ïí Çæä (i3)66
4-1-18- ØíÝ IR ÊјíÈ 7-(Ýäíá) – H7-ÈíÓ-[1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-
Ïí Çæä (j3)68
ãÑÇÌÚ70
˜íÏå ÇäáíÓí
˜íÏå
íÑÇäåÇ ÏÓÊå ãåãí ÇÒ ÊјíÈÇÊ Âáí ÑÇ ÊÔ˜íá ãíÏåäÏ ˜å ÏÇÑÇí ÎæÇÕ ÏÇÑæíí æ ÈíæáæŽí˜í ãÎÊáÝ åÓÊäÏ æ ÏÑ ÓÇÎÊ ÊÑí ÊíÏåÇíí ãÇääÏ ÞÇэåÇ¡ ÍÔÑå ˜ÔåÇ¡ ãæÇÏ ÖÏ æíÑæÓ æ ÖÏ ÊÔäÌ Èå ˜ÇÑ ãíÑæäÏ.
ÏÑ Çíä ÊÍÞíÞ ÈÑÇí Çæáíä ÈÇÑ ÊјíÈÇÊ ÈíÓ ÈäÒæíÑÇäæ íÑÇä- 6¡ 8-Ïí Çæä ÇÒ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÇäæÇÚ ÂáÏåíÏåÇí ÂÑæãÇÊí˜ ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ ÏÑ í˜ ãÑÍáå æ ÏÑ ÔÑÇíØ ãáÇíã¡ ÒãÇä ˜æÊÇå æ ÈÇ ÈÇÒÏå ÈÇáÇ ÓäÊÒ ÔÏäÏ.
æÇŽÇä ˜áíÏí: 4-åíÏÑæ˜Óí ˜æãÇÑíä¡ ÂáÏåíÏ¡ ÈíÓ ÈäÒæ íÑÇäæ íÑÇä-6¡8- Ïí Çæä¡ ÓÏíã Ïí Ýäíá Âãíä-4- ÓæáÝæäÇÊ
ÝÕá Çæá
ãÞÏãå æ ÊÆæÑí
1-1- ãÞÏãå
íÑÇäåÇ ÏÓÊå ãåãí ÇÒ åÊÑæÓí˜á åÇí ÍáÞæí ÈÇ ÝÚÇáíÊ åÇí ÈíæáæŽí˜í ãÎÊáÝ ÔÇãá ÖÏ ÓÑØÇä¡ ÖÏ Óá¡ ÖÏ HIV¡ ÖÏ ÞÇэ¡ ÖÏ ãí˜ÑæÈ¡ ÖÏ ÇáÊåÇÈ æ ÖÏ æíÑæÓ åÓÊäÏ. ÈäÇÈÑÇíä ÓäÊÒ ãÔÊÞÇÊ íÑÇäåÇ ÏÑ Ôíãí Âáí ÇÒ ÇåãíÊ ÒíÇÏí ÈÑÎæÑÏÇÑ ÇÓÊ ]1-10[.
ÏÑ Çíä ÑæŽå ÓäÊÒ ãÔÊÞÇÊ íÑÇäæ íÑÇäåÇ ÇÒ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇí ÂÑæãÇÊí˜ ãÎÊáÝ ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ ÈÑÑÓí ÔÏå ÇÓÊ.
1-2-˜æãÇÑíä
ÇÒ ÌæÔ ÎæÑÏä ÈäÒä ÈÇ ˜ÇÊíæä íÑíáíæã æ íÑæä åÇ ÊјíÈÇÊí ÍÇÕá ãíÔæäÏ ˜å ÓÇÎÊÇÑ ÇÕáí ÓíÓÊã ÍáÞæí Ñæåí ÇÒ ÊјíÈÇÊ ãåã Âáí ÑÇ ÊÔ˜íá ãíÏåäÏ. Çíä ÓÇÎÊÇÑåÇí ÍáÞæí ˜ÇÊíæä ÈäÒæíÑíáíæã (1)¡ ˜æãÇÑíä (2) æ ˜Ñæãæä (3) åÓÊäÏ.

Ô˜á 1-1-ÓÇÎÊÇÑ ÈÑÎí åÊÑæÓí˜á åÇí ÍÇæí åÓÊåí íÑÇä
ãÔÊÞÇÊ ˜æãÇÑíä ØÈÞå ãåãí ÇÒ ÊјíÈÇÊ Âáí ÑÇ ÊÔ˜íá ãíÏåäÏ. Çíä ÊјíÈÇÊ ÏÇÑÇí ÎæÇÕ ÏÇÑæíí äÙíÑ ÖÏ ÓÑØÇä¡ ÖÏ HIV¡ ÖÏ ÇäÚÞÇÏ Îæä¡ ÖÏ ÊÔäÌ åÓÊäÏ. ÚáÇæå ÈÑÇíä ˜æãÇÑíä åÇ ÏÑ ÕäÇíÚ ÚØÑÓÇÒí¡ áæÇÒã ÂÑÇíÔí æ ÕäÇíÚ ãÑÊÈØ ÈÇ ÂäåÇ æ åãäíä ÏÑ ÒãíäååÇí ÈíæáæŽí˜í¡ áíÒÑ æ ÕäÇíÚ ÛÐÇíí Èå ˜ÇÑ ÈÑÏå ãíÔæäÏ. ÏÑ ÚØÑÓÇÒí Èå ÚäæÇä ÊËÈíÊ ˜ääÏå æ ÏÑ ÑæÛä ØÈíÚí ÈÑÇí ÇÝÒÇíÔ Èæ Èå ˜ÇÑãí ÑæäÏ. åãäíä ÂäåÇ Èå ØæÑ æÓíÚí ÏÑ ãØÈæÚ ˜ÑÏä Èæí ãÍÕæáÇÊ ÕäÚÊí æ íÇ ãÎÝí ˜ÑÏä Èæí äÇãØÈæÚ ãËá Èæí íÏæÝÑã æ Èæí Ýäæáí Èå ˜ÇÑ ãíÑæäÏ. ÇÝÒæÏä ˜æãÇÑíä Èå ÍãÇã ÂÈ ÝáÒ˜ÇÑí¡ ãæÌÈ ÊÓåíá Êå äÔíä ÔÏä ÝáÒåÇ æ ÈäÇÈÑÇíä ˜ÇåÔ ÊÎáÎá æ ÇÝÒÇíÔ ÏÑÎÔäϐí ÝáÒ ãíÔæÏ. 6-ãÊíá ˜æãÇÑíä ÏÑ ÇÔäíåÇí ãÕäæÚí æ åãäíä Èå ÚäæÇä ÊÚÏíá ˜ääÏå ÏÑ ÚØÑåÇ Èå ˜ÇÑãí ÑæÏ ]11-18[.
í˜ Óã ØÈíÚí ÏÑÔÈÏÑ¡ ãÔÊÞí ÇÒ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÇÓÊ. ÇÒ Çíä ÎÇÕíÊ ÏÑ ÏÇÑæÓÇÒí æ ÈÑÇí ÏÑãÇä ÈíãÇÑíåÇí ÞáÈí æ ÚÑæÞí ÇÓÊÝÇÏå ãíÔæÏ. ÏÑ ãíÇä ÎæÇÕ ãÎÊáÝ ÈíæáæŽí˜í ˜æãÇÑíä åÇ¡ ÝÚÇáíʝåÇí ÖÏ ÊæãæÑ æ ÌáæíÑí ÇÒ Ê˜ËíÑ ãæÑÏ ÊæÌå ÇÓÊ. ÏÑ Çíä ÑÇÓÊÇ¡ ãÔÎÕ ÔÏå ÇÓÊ ˜å ÈÑÎí ÇÒ ãÔÊÞÇÊ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ í˜ Ñæå ÂÑíá ÏÑ ãæÞÚíÊ 3-åÓÊå¡ ÈÇÚË ÌáæíÑí ÇÒ ÑÔÏ Óáæá ãíÔæÏ. ÈÚáÇæå ÒÇÑÔ ÔÏå ÇÓÊ ˜å ÓÇÏåÊÑíä ãÔÊÞ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÓÈÈ Èåã ÑíÎʐí ÇÓ˜áÊ Óáæá ÇäÊÎÇÈí ÏÑ ÓáæáåÇí ãáÇäæã ãíÔæÏ. ÏÑ Çíä Òãíäå¡ í˜ ÓÑí ÌÏíÏ ÇÒ Çíä ãÔÊÞÇÊ ÓäÊÒ æ ÈÑÑÓí ÔÏå ÇäÏ .
Ô˜á 1-2-ÓÇÎÊÇÑ 4-åíÏÑæ˜Óí ˜æãÇÑíä
˜æãÇÑíä ÏÑ íÇåÇä ÚáæÝå Çí ÊíÑå äÎæÏ ÇåãíÊ ÒíÇÏí ÏÇÑÏ ÒíÑÇ Èå ÏäÈÇá ÊÛííÑÇÊí ˜å ÈÇ ÈǘÊÑíåÇ íÏÇ ã흘äÏ Èå Ïí ˜æãÇÑæá ÊÈÏíá ãíÔæÏ ˜å ãÇÏåÇí ÖÏ ÇäÚÞÇÏ ÈæÏå æ ÚÇãá ÎæäÑíÒí ÏÇãåÇ ÇÓÊ ]20 [.
˜æãÇÑíäåÇí ÏÇÑÇí ÇÓ˜áÊ åÊÑæÓí˜á ¡ í˜í ÇÒ ãåãÊÑíä Ñæå Ñ䐝åÇí ÝáæÆæÑÓÇäÓí æ ÏÑÎÔÇä ˜ääÏååÇ åÓÊäÏ. ˜ÇÑÈÑÏ ÊÚÏÇÏí ÇÒ ˜æãÇÑíäåÇ ÏÑ ãæÇÏ Çá˜ÊÑæǁÊí˜ ãÇääÏ Ñä áíÒÑ¡ ãæÇÏ ÂÊÔ íÑ Âáí æ ãæÇÏ ÍÓÇÓ ÝæÊæ Çá˜ÊÑæäí˜ ÈÑÑÓí ÔÏå ÇÓÊ ]21[.
ÈÑÎí ÇÒ ÊјíÈÇÊ ÏÇÑæíí ˜æãÇÑíä åÇ ÏÑ Ô˜á 1-3 äÔÇä ÏÇÏå ÔÏå ÇÓÊ:

Ô˜á 1-3-ÊјíÈÇÊ ÏÇÑæíí ÏÇÑÇí ÓÇÎÊÇÑ ˜æãÇÑíäí
1-2-1- æǘäÔ åÇí ˜æãÇÑíä
1-2-1-1 ǘÓÇíÔ
˜æãÇÑíä ÈÓíÇÑ ÓÎÊ Ç˜ÓíÏ ãíÔæÏ. Çíä ÊјíÈ ÏÑ ãÞÇÈá ÇÓíÏ ˜Ñæãí˜ ÇíÏÇÑ ÇÓÊ¡ ÈÇ Çíä æÌæÏ ÇÛáÈ ÏÑ
Çíä ÊјíÈ Íãáå Èíæ ÔíãíÇíí-ǘÓÇíÔí ÏÑ ãæÞÚíÊ 7 ÇÊÝÇÞ ãíÇÝÊÏ ]22 [.
1-2-1-2-˜ÇåÔ
˜æãÇÑíä ÈÇ ãáÛãå ÓÏíã æ Ìíæå Èå ãáíáæÊí˜ ÇÓíÏ íÇ ÇÑÊæ åíÏÑæ˜Óí åíÏÑæÓíäÇãí˜ ÇÓíÏ (9) ˜ÇåÔ ãííÇÈÏ ]22 [.
Ô˜á 1-4 ÓÇÎÊÇÑ ãáíáæÊí˜ ÇÓíÏ
1-2-1-3- åíÏÑæáíÒ
ÊјíÈ áǘÊæäí ˜æãÇÑíä ÈÇ ÌæÔÇäÏä ÏÑ ÍÖæÑ ÊÇÓíã ˜ÑÈäÇÊ æ íÇ ÈÇ ÈÇÒåÇíí ãÇääÏ ÓÏíã åíÏÑæ˜ÓíÏ ÑÞíÞ Èå ä㘠˜æãÇÑí˜ ÇÓíÏ æ ÓÓ ÓíÓ ÇÑÊæ åíÏÑæ˜Óí ÓíäÇãí˜ ÇÓíÏ (10)¡ åíÏÑæáíÒ ãíÔæÏ. ÏÑ ÍÇáí˜å Ñã ˜ÑÏä ˜æãÇÑíä ÈÇ ÊÇÓíã åíÏÑæ˜ÓíÏ ÛáíÙ ÇÈÊÏÇ ä㘠˜æãÇÑí˜ ÇÓíÏ æ ÓÓ ÊÑÇäÓ ÇÑÊæ åíÏÑæ˜Óí ÓíäÇãí˜ ÇÓíÏ (11) ãí ÏåÏ ]23 [.

Ô˜á 1-5- ãÍÕæáÇÊ åíÏÑæáíÒ ˜æãÇÑíä
1-2-1-4- åÇáæŽä ÏÇÑ ÔÏä ˜æãÇÑíä
ÇÒ æǘäÔ ˜æãÇÑíä ÈÇ ÈÑã¡ ÇÈÊÏÇ ãÍÕæá ÇÝÒÇíÔí Ïí ÈÑãæ 12 Èå ÏÓÊ ãíÂíÏ. ÏÑ ãÑÍáå ÈÚÏ¡ ÈÇÍÐÝ HBr
3-ÈÑãæ ˜æãÇÑíä (13) ÊæáíÏ ãíÔæÏ ]24-25 [.
ØÑÍ 1-1: æǘäÔ ÈÑã ÏÇÑ ÔÏä ˜æãÇÑíä
1-2-1-5- äíÊÑæ ÏÇÑ ÔÏä ˜æãÇÑíä
æǘäÔ ˜æãÇÑíä ÈÇ äíÊÑí˜ ÇÓíÏ ÏæÏ ˜ääÏå ÈÇÚË ÌÇíÒíäí Ñæå äíÊÑæ ÏÑ ÍáÞå ÈäÒäí ãíÔæÏ æ 6- äíÊÑæ
˜æãÇÑíä (14) Èå ÚäæÇä ãÍÕæá ÇÕáí æ 8-äíÊÑæ˜æãÇÑíä (15) Èå ÚäæÇä ãÍÕæá ÝÑÚí ÊæáíÏ ãíÔæÏ
]24-25 [.
ØÑÍ 1- 2: æǘäÔ äíÊÑæ ÏÇÑ ÔÏä ˜æãÇÑíä
1-2-2- Êåíå ˜æãÇÑíä åÇ
ÏÑ ÓÇá 1820 Çá˜áí ÇÒ ÏÇäå Êä˜Ç ÇÓÊÎÑÇÌ ÔÏ ˜å ÔÇãá %5/1 ˜æãÇÑíä ÈæÏ. Çíä Ôíæå Èå ÚäæÇä Çæáíä ÑæÔ Êåíå ˜æãÇÑíä ÔäÇÎÊå ÔÏ æ ÊÇ ÓÇá 1868 Èå ÚäæÇä ÊäåÇ ãäÈÚ Êåíå ˜æãÇÑíä ÈÇÞí ãÇäÏ ÊÇ Çíä˜å ÑæԝåÇí ÓäÊÒí Ñ˜íä ÌÇíÒíä ãäÇÈÚ ØÈíÚí ÔÏ. ÈíÔÊÑ ˜æãÇÑíäåÇ ˜å ÏÑ íÇåÇä æÌæÏ ÏÇÑäÏ ÇÒ ØÑíÞ ÇÓÊÎÑÇÌ ÈÇ ÍáÇáåÇí ãäÇÓÈ ÌÏÇÓÇÒí ãíÔæäÏ. ˜æãÇÑíä åÇ ãÇÏå ÇÓÇÓí Èæ ÑÇ ÏÑ í˜ ÓÑí ÇÒ æäååÇí íÇåí ÊÔ˜íá ãíÏåäÏ. Çíä ãæÇÏ ÏÑ ÑæÛä ÇÓØæÎæÏæÓ¡ ˜ÇÓíÇ¡ ÑæÛäåÇí ãјÈÇÊ¡ á ÍäÇ¡ ÔÇå ÈáæØ¡ ÈÇÈæäå æ ÏÑ 60 æäå íÇåÇä æÌæÏ ÏÇÑäÏ. ÏÑ æÇÞÚ íÇåÇä ãåãÊÑíä ãäÈÚ ˜æãÇÑíäåÇ åÓÊäÏ ÇãÇ ÇÓÊÎÑÇÌ ÇÒ ÂäåÇ ãáÇá ÂæÑ æ ÒãÇä ÈÑ ÇÓÊ æ äíÇÒ Èå ÏÓʐÇååÇí ííÏå ÏÇÑÏ.
ÈÓíÇÑí ÇÒ ÑæԝåÇí ÓäÊÒí ãÇääÏ ÑæÔ ÊÑǘ㠁ãä¡ Ñ˜íä¡ ÑÝæÑãÇÊÓ˜í¡ æǘäÔ æíÊ퐡 ÊÑǘã äææäǐá æ äæÂÑÇíí ˜áÇíÒä ÈÑÇí ÓäÊÒ ˜æãÇÑíä ãæÑÏ ÈÑÑÓí ÞÑÇÑ ÑÝÊåÇäÏ. æǘäÔ ÊÑǘãí ãä ÂÓÇäÊÑíä æ ãÊÏÇæáÊÑíä ÑæÔ ãæÑÏ ÇÓÊÝÇÏå ÈÑÇí Êåíåí ˜æãÇÑíäåÇ ÇÓÊ æ ÇÒ ØÑíÞ ÊÑǘã Ýäæá ÈÇ ?-˜ÊæÇÓÊÑåÇ ÏÑ ÍÖÜæÑ ˜ÇÊÇáíÒÑ ÇÓíÏ áæÆíÓ æ ÇÒ ØÑíÞ ÊÈÇÏá ÇÓÊÑí ˜ÇÊÇáíÒ ÔÏå ÈÇ ÇÓíÏ¡ ÊæÊæãÑÔÏä ˜Êæ- Çäæá¡ ÇÝÒÇíÔ ãÇí˜á æ ÂÈÒÏÇíí ˜ÇÊÇáíÒ ÔÏå ÈÇ ÇÓíÏ ÇäÌÇã ã흐íÑÏ. ÚãæãÇð ÓæáÝæÑí˜ ÇÓíÏ ÛáíÙ ¡ ÊÑí ÝáæÆæÑæÇÓÊí˜ ÇÓíÏ æ íÇ ÝÓÝÑæ Ýäæ˜ÓÇíÏ ÈÑÇí ÓäÊÒ ˜æãÇÑíä æ ãÔÊÞÇÊÔ ÇÓÊÝÇÏå ãíÔæÏ. ÚáÇæå ÈÑ Âä ÇÓÊÝÇÏå ÇÒ ÏíÑ ˜ÇÊÇáíҐÑåÇí åãä åãÇääÏ ˜áÑíÏåÇí ÝáÒí æ ÓæáÝæäí˜ ÇÓíÏ Èå ÚäæÇä ˜ÇÊÇáíÒÑ ÇÓíÏí ÏÑ æǘäÔ ãä ÒÇÑÔ ÔÏå ÇÓÊ ]26-33[.
ØÑÍ 1-3: Êåíå ˜æãÇÑíä ÇÒ ÊÑǘã Ýäá ÈÇ ?- ˜ÊæÇÓÊÑåÇ
1-2-3- ˜ÇÑÈÑÏ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÏÑ ÓäÊÒ ÊјíÈÇÊ Âáí
ãÞÇáÇÊ ÒíÇÏí ÏÑ ãæÑÏ æǘäԝåÇí 4-åíÏÑæ˜Óí ˜æãÇÑíä ÒÇÑÔ ÔÏå ÇÓÊ ˜å ÏÑ ÒíÑ Èå ÈÑÎí ÇÒÂäåÇ ÇÔÇÑå ÎæÇåÏ ÔÏ.
1-2-3-1- ÓäÊÒ ÈíÓ-˜æãÇÑíä
æǘäԝ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇ ÏÑ ÍÖæÑ ˜ÇÊÇáíҐÑåÇí ãÎÊáÝí äÙíÑ ¡ ¡ ¡ ¡ ¡ ¡ ¡¡ ¡ ¡ ÈÑÑÓí ÔÏå ÇÓÊ ˜å ÏÑ ÂäåÇ ÈíÓ ˜æãÇÑíä 21¡ ãÍÕæá ÇÕáí ÈæÏå ÇÓÊ (ÌÏæá1-1).
ØÑÍ 1-4: Êåíå ÈíÓ ˜æãÇÑíä ÇÒ ÊÑǘã 4- åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇí ÂÑæãÇÊí˜
ÌÏæá 1-1- ÈÑÑÓí ÓäÊÒ ÈíÓ ˜æãÇÑíä ÏÑ ÍÖæÑ ˜ÇÊÇáíҐÑåÇí ãÎÊáÝ
ÑÏíݘÇÊÇáíҐÑÍáÇáÏãÇ ÒãÇä(min)ÈÇÒÏå %ÔÑÇíØ æǘäÔãÑÌÚ1ÇÊÇäæá æ ÂÈ(1:1)706-398-81ÍÑÇÑÊ ˜áÇÓí˜2ÂÈ25h655ÑÝáǘÓ3ÂÈ8030-1095-85ÑÝáǘÓ41ÇÊÇäæá1001095ÑÝáǘÓ5ÇÊÇäæá æ ÂÈ (1:1)1003068ÑÝáǘÓ62ÇÊÇäæá æ ÂÈ (1:1)1009080ÑÝáǘÓ7Ïí ˜áÑæãÊÇä ÎÔ˜401892ÍÑÇÑÊ ˜áÇÓí˜8ãÊÇäæá2527-590~74ÑÝáǘÓ9ÂÈ8030-2590- 74ÑÝáǘÓ103 ÇÊÇäæá78590~ÑÝáǘÓ* æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇ ÏÑ ÔÑÇíØ ãÎÊáÝ
1-2-3-2- ÓäÊÒ ãÔÊÞÇÊ íÑÇäæíÑÇäåÇ
ÓäÊÒ ãÔÊÞÇÊ íÑÇäæ íÑÇä åÇ ÏÑ Ïæ ãÑÍáå ÇÒ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇ ÏÑ ÍÖæÑ ˜ÇÊÇáíҐÑåÇí ¡ ¡ p ÒÇÑÔ ÔÏå ÇÓÊ ÏÑ Çíä ÑæÔåÇ ÇÈÊÏÇ ãÔÊÞÇÊ ÈíÓ ˜æãÇÑíä Èå ÕæÑÊ ÍÏ æÇÓØ ÌÏÇ æ ÓÓ Øí í˜ ÝÑÇíäÏ ÍáÞæí ÔÏä æ ÈÇ ÍÐÝ í˜ ãæá˜æá ÂÈ ãÔÊÞÇÊ íÑÇäæ íÑÇä åÇ Èå ÏÓÊ ÂãÏäÏ.
ØÑÍ 1-5: Êåíå ãÔÊÞÇÊ íÑÇäæ íÑÇäåÇ ÇÒ ÊÑǘã 4- åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇí ÂÑæãÇÊí˜
ÌÏæá 1-2- ÈÑÑÓí ÓäÊÒ ãÔÊÞÇÊ íÑÇäæíÑÇäåÇ ÏÑ ÔÑÇíØ ãÎÊáÝ
ÑÏíݘÇÊÇáíҐÑÍáÇáÏãÇ ((ÒãÇä (h)ÈÇÒÏå %ÔÑÇíØ æǘäÔãÑÌÚ1Ïí ˜áÑæãÊÇä80680-60ÍÑÇÑÊ ˜áÇÓí˜2ÇÊÇäæá37580-65ÑÝáǘÓ3p-TsOHÇÓÊí˜ ÇÓíÏ805/292ÍÑÇÑÊ ˜áÇÓí˜
ÝÕá Ïæã
ÈÍË æ äÊíÌå íÑí
2-1- åÏÝ ÊÍÞíÞ
˜æãÇÑíä åÇ ÊјíÈÇÊí ÈÇ ÎæÇÕ ÏÇÑæíí ãÊÚÏÏ åÓÊäÏ. ÇÒ ÂäåÇ Èå ØæÑ ÓÊÑÏå ÏÑ ÝÚÇáíʝåÇí ÏÇÑæíí ãÇääÏ ÖÏ ÓÑØÇä¡ ÖÏ ÇäÚÞÇÏ Îæä¡ ÖÏ ÊÔäÌ ÇÓÊÝÇÏå ãíÔæÏ. 4-åíÏÑæ˜Óí ˜æãÇÑíä ÇÒ ÎÇäæÇÏå ãæÇÏ ÖÏ æíÊÇãíä K æ ÖÏ ÇäÚÞÇÏí ÇÓÊ. ãæÇÏ ÏÇÑæíí ˜å ãÚãæáÇð ÇÒ ÂäåÇ ÓÇÎÊå ãíÔæÏ¡ ÇÒ ØÑíÞ ÇÝÒÇíÔ í˜ ÇÓÊÎáÇÝ ÈÒѐ ÏÑ ãæÞÚíÊ 3 (˜ÑÈä ÍáÞå Èíä ÑæååÇí åíÏÑæ˜Óíá æ˜ÑÈæäíá) ÈÏÓÊ ãíÂíäÏ. Çíä ÇÓÊÎáÇÝ ÈÒѐ ÈÑÇí ÝÚÇáíʝåÇí ÖÏ ÇäÚÞÇÏí äíÇÒ ÇÓÊ ]47-48 [.
ÏÑ ÈíÔÊÑ ÒÇÑԝåÇí ÇÑÇÆå ÔÏå ÇÒ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇ ãÍÕæá ÇÕáí ÈíÓ ˜æãÇÑíä ÇÓÊ ˜å ÈÑÎí ÇÒ Çíä ÑæԝåÇ ÏÑ ÝÕá Çæá ÇÔÇÑå ÔÏå ÇÓÊ. ÏÑ Çíä ÊÍÞíÞ ÓäÊÒ ãÔÊÞÇÊ íÑÇäæ íÑÇäåÇ ÈÕæÑÊ Ê˜ ãÑÍáå Çí ÇÒ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä æ ÂáÏåíÏåÇí ÂÑæãÇÊí˜ ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ ÈÑÑÓí ÔÏå ÇÓÊ.
2-2- ÈÍË æ ÈÑÑÓí
æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ 3-ÈÑãæ ÈäÒ ÂáÏåíÏ (ÈÇ äÓÈÊ ÇÓÊæ˜íæãÊÑí 2 Èå 1) Èå ÚäæÇä ãÏá ÇäÊÎÇÈ æ Çã˜Çä ÇäÌÇã æǘäÔ ÏÑ ÏãÇí60 ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ æ ÏÑ ÔÑÇíØ ÈÏæä ÍáÇá ÈÑÑÓí ÔÏ. Ó ÇÒ äÏ ãÑÍáå ÔÓÊÔæ ÈÇ ÂÈ ÏÇÛ æ ÇÊÇäæá 96ÏÑÕÏ ÑÓæÈ ÓÝíÏ ÎÇáÕ ÈÇ ÈÇÒÏå 85 ÏÑÕÜÜÏ æ ÏãÜÜÇí ÐæÈ 300< ÊÔ˜íá ÔÜÜÏ. ÓÇÎÊÇÑ ãÍÕÜÜæá ÈÇ ØíÝ ÓäÌÜí IR¡ H NMR¹æ
C NMR¹³ ÊÃííÏ ÔÏ.
ØÑÍ 2-1- ÓäÊÒ 7-(3-ÈÑãæ Ýäíá) – H7- ÈíÓ [1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí Çæä
ÓÇÎÊÇÑ ÊјíÈ ÈÇ ØíÝ Èíäí IR ãæÑÏ ÊÃííÏ ÞÑÇÑ ÑÝÊ. ØíÝ IR Çíä ÊјíÈ Èå ÕæÑÊ ÞÑÕ KBr ËÈÊ ÔÏ. ØíÝ ÍÇæí ÇÑÊÚÇÔÇÊ ˜ÔÔí æ ÎãÔí ãæÑÏ äÙÑ ÈæÏ (Ô˜á ?-3).
ØíÝ IR ¡ ÇÑÊÚÇÔ ˜ÔÔí -HC ÂÑæãÇÊí˜í ÑÇ ÏÑ 3063¡ ÇÑÊÚÇÔ ˜ÔÔí -HC ÂáíÝÇÊí˜í ÑÇ ÏÑ
2933¡ ÇÑÊÚÇÔ ˜ÔÔí C=O ÑÇÏÑ 1653¡ ÇÑÊÚÇÔ ˜ÔÔí ÑÇ ÏÑ 1613¡ 1467¡ ÇÑÊÚÇÔ ˜ÔÔí O-C ÇÓÊÑí ÑÇ ÏÑ 1188 æ ÇÑÊÚÇÔ ˜ÔÔí Br-C ÑÇ ÏÑ 1051 äÔÇä ãíÏåÏ.
Ô˜á ?-1-ØíÝ IR ÊјíÈ ? -(3-ÈÑãæÝäíá) – H7- ÈíÓ [1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí Çæä
ØíÝ H NMR¹(MHz400) ÊјíÈ ÏÑ ÍáÇá 6d-DMSO¡ ÌÇÈÌÇíí ÔíãíÇíí (ppm¡ ) ÑæÊæä a ÑÇ Èå ÕæÑÊ í˜ÊÇíí ÏÑ 27/6¡ ÑæÊæä e ÑÇ Èå ÕæÑÊ ÏæÊÇíí- ÏæÊÇíí ÏÑ 11/7 ÈÇ ËÇÈÊ ÌÝÊ ÔÏä 8/7 æ 2/1 åÑÊÒ¡ ÑæÊæä d ÑÇ ÈÕæÑÊ Óå ÊÇíí ÏÑ 16/7 ÈÇ ËÇÈÊ ÌÝÊ ÔÏä 6/7 åÑÊÒ¡ ÑæÊæä c ÑÇ Èå ÕæÑÊ äÏ ÊÇíí ÏÑ 20/7¡ ÑæÊæä h ÑÇ Èå ÕæÑÊ ÏæÊÇíí-Óå ÊÇíí ÏÑ 26/7 ÈÇ ËÇÈÊ ÌÝÊ ÔÏä 8/7 æ 2/1 åÑÊÒ¡ ÑæÊæäåÇí f æ b ÑÇ Èå ÕæÑÊ äÏÊÇíí ÏÑ 27/7-30/7¡ ÑæÊæä g ÑÇ Èå ÕæÑÊ ÏæÊÇíí-Óå ÊÇíí ÏÑ 54/7 ÈÇ ËÇÈÊ ÌÝÊ ÔÏä 6/7 æ 6/1 åÑÊÒ¡ æ ÑæÊæä l ÑÇ Èå ÕæÑÊ ÏæÊÇíí- ÏæÊÇíí ÏÑ 84/7 ÈÇ ËÇÈÊ ÌÝÊ ÔÏä 0/8 æ 6/1 åÑÊÒ äÔÇä ãíÏåÏ.
Ô˜á ?-2- ØíÝ H NMR¹(MHz400) ÊјíÈ 7-(3-ÈÑãæÝäíá)- H7- ÈíÓ [1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí Çæä
Ô˜á 2-3-ØíÝ H NMR¹(MHz400) ÈÇÒ ÔÏå ÊјíÈ 7-(3-ÈÑãæÝäíá)- H7- ÈíÓ [1] ÈäÒæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí Çæä
ØíÝ C NMR ¹³ ÊјíÈ ÝæÞ ÏÑ ÍáÇá 6d-DMSO¡ ÌÇÈÌÇíí ÔíãíÇíí (mpm¡ ?) ˜ÑÈä ÂáíÝÇÊí˜í ÑÇ ÏÑ 5/36¡ ˜ÑÈä O=C ÇÓÊÑí ÑÇ ÏÑ 7/167 æ ˜ÑÈäåÇí ÏíÑ ÑÇ 5/103¡ 1/116¡ 8/119¡ 8/121¡ 6/123¡ 5/124¡ 4/126¡ 5/128¡ 6/129¡ 5/130¡ 8/131¡ 6/145¡ 9/152 æ 9/164 äÔÇä ãíÏåÏ (Ô˜á2-4 æ 2-5).
Ô˜á 2-4-ØíÝ 13C NMR (MHz100) ÊјíÈ 7-(3-ÈÑãæÝäíá)- H7- ÈíÓ [1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí Çæä
Ô˜á 2-5-ØíÝ 13C NMR (MHz001) ÈÇÒ ÔÏå ÊјíÈ 7-(3-ÈÑãæÝäíá)- H7- ÈíÓ [1] ÈäÒæ íÑÇäæ [3¡4- b:´3¡´4-e] íÑÇä-6¡8-Ïí Çæä
2-2-1- ã˜ÇäíÓã æǘäÔ
ã˜ÇäíÓ㠁íÔäåÇÏí ÈÑÇí Çíä æǘäÔ ÏÑ ØÑÍ 2-2 ÂæÑÏå ÔÏå ÇÓÊ.
ØÑÍ 2-2: ã˜ÇäíÓ㠁íÔäåÇÏí ÈÑÇí Êåíå ãÔÊÞÇÊ íÑÇäæ íÑÇäåÇ ÇÒ ÊÑǘã 4- åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏåÇí ÂÑæãÇÊí˜
2-2-2 – ÈÑÑÓí ÚæÇãá ãÄËÑ ÈÑ æǘäÔ
2-2-2-1-ÇËÑ ˜ÇÊÇáíҐÑ
ÈÇ ÊæÌå Èå Çíä˜å äæÚ ˜ÇÊÇáíÒÑ åã ãíÊæÇäÏ ÏÑ ÓÑÚÊ ÇäÌÇã æǘäÔ ãÄËÑ ÈÇÔÏ ÈäÇÈÑÇíä æǘäÔ ÏÑ ÍÖæÑ Ïæ ˜ÇÊÇáíÒÑ ÏíÑ äíÒ ÏÑ ÏãÇí C°60 ÈÑÑÓí ÔÏ ˜å ÈåÊÑíä äÊíÌå ÈÑÇí Çíä æǘäÔ ÇÓÊÝÇÏå ÇÒ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä- 4-ÓæáÝæäÇÊ ÈÇ ÈÇÒÏå ÈÇáÇ æ ÒãÇä ˜ã ÈÏÓÊ ÂãÏ.
ÌÏæá 2-1- ÈÑÑÓí ÇËÑ ˜ÇÊÇáíÒÑ ÏÑ ÓäÊÒ ÊјíÈ a3
ÈÇÒÏå (%)ÒãÇä (nmi)äæÚ ˜ÇÊÇáíҐÑÑÏíÝ8215Sodium diphenylamine-4-solfunate180120[Hmim]HSO4245120[Bmim]Br3* ÔÑÇíØ æǘäÔ: 4- åíÏÑæ˜Óí ˜æãÇÑíä (1 ãíáí ãæá)¡ ÂáÏåíÏ (5/0 ãíáí ãæá)¡ ÑæÔ ÑãÇÏåí ãÚãæáí¡ ÈÏæä ÍáÇá¡ ÏãÇí C°60
2-2-2-2 – ÇËÑ ÏãÇ
æä ÏãÇ ÈÑ ÓÑÚÊ æǘäÔ ãÄËÑ ÇÓÊ¡ ÓäÊÒ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏ ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ ÏÑ ÏãÇåÇí C° 100¡ C° ?5¡ C° 60¡ C° 40 æ ÏãÇí ÇÊÇÞ C° 25 ÏÑ ÍãÇã ÑæÛä ÈÑÑÓí æ ãÚáæã ÔÏ ˜å Çíä æǘäÔ ÏÑ ÏãÇí C° 60 ÈÇ ÈÇÒÏå ÈíÔÊÑ ÏÑ ÒãÇä ãäÇÓȝÊÑí ÇäÌÇã ãíÔæÏ (ÌÏæá 2-2).
ÌÏæá 2-2- ÈÑÑÓí ÇËÑ ÏãÇ ÈÑ ÓäÊÒ ÊјíÈ a3
ÈÇÒÏå (%)ÒãÇä (min)ÏãÇ (C°)ÑÏíÝ706025178304028?1?6038?1?8548?1?1005* ÔÑÇíØ æǘäÔ: 4- åíÏÑæ˜Óí ˜æãÇÑíä (1 ãíáí ãæá)¡ ÂáÏåíÏ (5/0 ãíáí ãæá)¡ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4- ÓæáÝæäÇÊ (g 1/0)¡ ÑæÔ ÑãÇÏåí ãÚãæáí¡ ÈÏæä ÍáÇá¡ ÏãÇ C? 60
2-2-3-ÓäÊÒ ãÔÊÞÇÊ ÌÏíÏ
ÈÑÇí ÈÑÑÓí ˜ÇÑÇíí Çíä ÑæÔ¡ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÇäæÇÚ ÂáÏåíÏåÇí ÂÑæãÇÊí˜ ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ ÇäÌÇã ÔÏ äÊÇíÌ Âä äÔÇä ãí ÏåÏ ˜å ÇÓÊÎáÇÝ åÇí Çá˜ÊÑæä ÏåäÏå íÇ ˜ÔäÏå ÈÑ Ñæí ÍáÞå ÂáÏåíÏ ÊÃËíÑ ÒíÇÏí ÈÑ ÓÑÚÊ æ ÈÇÒÏå æǘäÔ äÏÇÑÏ ÇãÇ ÂáÏåíÏåÇí ÇÑÊæ ãÍÕæá ÑÇ ÈÇ ÈÇÒÏå ˜ãÊÑí Èå ÏÓÊ ãí ÏåÏ.
ØÑÍ 2-3
ÌÏæá 2-3- ãÍÕæáÇÊ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏ ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä 4-ÓæáÝæäÇÊ ÏÑ ÏãÇí C? 60 æ ÈÏæä ÍáÇá
ãÍÕæáÇÊRÒãÇä(min)ÈÇÒÏå (%)ÏãÇí ÐæÈ (C°)ÏãÇí ÐæÈ ÒÇÑÔ ÔÏå ]ãÑÌÚ[a33-Br1585300>b34-C l1573252-250c34-Br1582267-265d34-NO22070300>e33-NO21572226-224]49[ 218 f32-Cl2065275-273]49[ 277-274 g32-NO22060228-226h34-OCH33090240-238]50[ 185 i34-N(CH3) 23092224-222j3H1075203-200]50[ 195 * ÔÑÇíØ æǘäÔ: 4- åíÏÑæ˜Óí ˜æãÇÑíä (1 ãíáí ãæá)¡ ÂáÏåíÏ (5/0 ãíáí ãæá)¡ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä- 4- ÓæáÝæäÇÊ (g 1/0)¡ ÏãÇ 60¡ ÑæÔ ÑãÇÏåí ãÚãæáí¡ ÈÏæä ÍáÇá
ãÔÊÞÇÊ ÓÇÎÊå ÔÏå ÏÑ Çíä ÊÍÞíÞ ÈÇ ÑæԝåÇí ÒÇÑÔ ÔÏå ]49-50[ ãÞÇíÓå æ ãÚáæã ÔÏ ˜å ÈÇ ÇÓÊÝÇÏå ÇÒ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4- ÓæáÝæäÇÊ ãÔÊÞÇÊ íÑÇäæ íÑÇäåÇ ÏÑ í˜ ãÑÍáå æ ÈÇ ÒãÇä æǘäÔ ˜ãÊÑ æ ÈÇÒÏå ÈÇáÇÊÑ ÊæáíÏ ãíÔæäÏ.
2-3-äÊíÌå íÑí
ÏÑ Çíä ÊÍÞíÞ ÊјíÈÇÊ ÌÏíÏ íÑÇäæ íÑÇäåÇ ÇÒ æǘäÔ 4-åíÏÑæ˜Óí ˜æãÇÑíä ÈÇ ÂáÏåíÏ Èå äÓÈÊ ÇÓÊæ˜íæãÊÑí 2 Èå 1 ÏÑ ÍÖæÑ ˜ÇÊÇáíÒÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ ÏÑ ÏãÇí C?60 æ ÈÏæä ÍáÇá ÓäÊÒ ÔÏåÇäÏ. ÈÇÒÏå ÈÇáÇ¡ ÒãÇä ˜æÊÇå æǘäÔ¡ ÇÓÊÝÇÏå ä˜ÑÏä ÍáÇá æ ˜ÇÊÇáíҐÑåÇí ÑÇä ÞíãÊ¡ ÌÏÇÓÇÒí ÂÓÇä ˜ÇÊÇáíÒÑ ÇÒ ãÍÕæá æ ÎÇáÕ ÓÇÒí ÂÓÇä ãÍÕæá ÇÒ ãÒíʝåÇí ÑæÔ ÇÑÇÆå ÔÏå ÇÓÊ.
íÔäåÇÏ ÈÑÇí ˜ÇÑåÇí ÂíäÏå:
• ÇÓÊÝÇÏå ÇÒ ˜ÇÊÇáíҐÑåÇí ÏíÑ
• ÇÓÊÝÇÏå ÇÒ ÂáÏåíÏåÇí åÊÑæÓí˜á æ ÂáíÝÇÊí˜
• ÇÓÊÝÇÏå ÇÒ Ê˜ä혝åÇí ÂÒãÇíԐÇåí ÏíÑ äÙíÑ ÑíÒ ãæÌ¡ ÝÑÇÕæÊ æ Çá˜ÊÑæÔíãí
ÝÕá Óæã
ÈÎÔ ÊÌÑÈí
3-1-ÈÎÔ ÊÌÑÈí
ÏãÇí ÐæÈ ÒÇÑÔ ÔÏå ÊÕÍíÍ äÔÏå ÇäÏ æ ÈÇ ÏÓʐÇå THERMO SCINTIFIC 9200 ÇäÏÇÒåíÑí ÔÏå ÇÓÊ. ØíݝåÇí ÒíÑ ÞÑãÒ ÈÇ ÏÓʐÇå 8600IR-FT SHIMADZU æ ØíݝåÇí H NMR¹ æ
C NMR¹³ ÈÇ ÏÓʐÇå ØíÝ ÓäÌ MHz BRUKER 400 ËÈÊ ÔÏå ÇÓÊ.
3-1-1-ÎÕæÕíÇÊ 4-åíÏÑæ˜Óí ˜æãÇÑíä
äÇã ÂíæÇ˜:2-åíÏÑæ˜Óí ˜Ñæãä-4-Çæä
äÇãåÇí ÏíÑ: 4-˜æãÇÑíäæá¡ ÈäÒæÊÊÑæäí˜ ÇÓíÏ æ 4-åíÏјÓí ˜æãÇÑíä
ÝÑãæá ãæá˜æáí: ÌÑã ãæáí: g/mol14/162
ÏãÇí ÐæÈ: C? 213-211 Ñä: æÏÑ ÓÝíÏ

Ô˜á 3-1-ÓÇÎÊÇÑ 4-åíÏÑæ˜Óí ˜æãÇÑíä
3-1-2-ÎÕæÕíÇÊ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ
ÝÑãæá ãæá˜æáí: S3NNaO10H12C ÌÑã ãæáí: 27/271
ÍáÇáíÊ ÏÑ ÂÈ: ÏÑ ÏãÇí C?20¡??? Ñã ÏÑ áíÊÑ ÍáÇáíÊ ÏÑ ÇÊÇäæá: ÏÑ ÏãÇí C?20¡ 5/? Ñã ÏÑ áíÊÑ
pH : 7/5 ( C?20¡ 10g/(l,H?O) ) Ñä ÑÓæÈ: ÎǘÓÊÑí ÏãÇí ÐæÈ: C?300<
Ô˜á 3-2- ÓÇÎÊÇÑ ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ
3-1-3-ÏÓÊæÑ ˜ÇÑ Úãæãí ÓäÊÒ íÑÇäæ íÑÇäåÇ j­a3
ÏÑ í˜ áæáå ÂÒãÇíÔ¡ 1 ãíáí ãæá 4-åíÏÑæ˜Óí ˜æãÇÑíä¡ 5/? ãíáí ãæá ÂáÏåíÏ j­a2 æ 1/? Ñã ÓÏíã Ïí Ýäíá Âãíä-4-ÓæáÝæäÇÊ ÇÖÇÝå ÑÏíÏ æ ÏÑ ÏãÇí C?60 ÏÑ ÍãÇã ÑæÛä¡ ÏÑ ÒãÇä ãäÇÓÈ (ÌÏæá 2-3) åãÒÏå ÔÏ. æǘäÔ ÊÇ ˜Çãá ÔÏä ÈÇ TLC ÏäÈÇá ÔÏ. ÓÓ Èå ãÎáæØ æǘäÔ ÂÈ ãÞØÑ ÇÖÇÝå ÔÏ æ ÑÓæÈ ÍÇÕá ÕÇÝ æ ÈÇ ÂÈ ÏÇÛ æ ÇÊÇäæá 96? ÓÑÏ ÔÓÊÔæ ÏÇÏå ÔÏ. ÓÇÎÊÇÑ ãÍÕæáÇÊ d-a3 ÈÇ ÑæԝåÇí
IR¡ H NMR¹ æ C NMR¹³ æ ãÍÕæáÇÊ j­e3 ÈÇ ÑæÔ IR ÊÃííÏ ÔÏ.
3-2- ÈÑÑÓí ÏÇÏååÇí ØíÝí
3-2-1- ÊјíÈ a3§
7-(3-Bromophenyl)-7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ: Ñä ÑÓæÈ
IR (KBr): 3063 (CH-aromatic), 2933 (CH-aliphatic), 1653 (C=O), 1612, 1467 (C=C), 1188 (C-O), 1051 (C-Br) cm-1.
1H NMR (400 MHz, DMSO-d6): : 6.27 (s, 1H, Ha), 7.11(dd, J = 7.8, 1.2 Hz, 1H, He), 7.16 (t, J = 7.6 Hz, 1H, Hd), 7.20 (m, 1H, Hc), 7.26 (dt, J = 7.8, 1.2 Hz, 2H, Hh), 7.27-7.30 (m, 3H, Hf, Hb), 7.54 (dt, J = 7.6, 1.6 Hz, 2H, Hg), 7.84 (dd, J = 8.0, 1.6 Hz, 2H, Hl) ppm.

13C NMR (100 MHz, DMSO-d6): ; 36.5, 103.5, 116.1, 119.8, 121.8, 123.6, 124.5, 126.4, 128.5, 129.6, 130.5, 131.8, 145.6, 152.9, 164.9, 167.7 ppm.
3-2-2- ÊјíÈ b3**
7-(4-Chlorophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ :Ñä ÑÓæÈ
m.p: 250-252
IR (KBr): 3060 (CH-aromatic), 2940 (CH-aliphatic), 1668 (C=O), 1610, 1490 (C=C), 1213 (C-O), 1097 (C-Cl) cm-1.
1H NMR (400 MHz, DMSO-d6): : 6.30 (s, 1H, Ha), 7.16 (d, J = 8.4 Hz, 2H, Hb), 7.26 (d, J = 8.4 Hz, 2H, Hc), 7.30 (t, J = 7.6 Hz, 2H, Hf), 7.35 (d, J = 8.0 Hz, 2H, Hd), 7.58 (dt, J = 7.8, 1.6 Hz, 2H, He), 7.89 (dd, J = 7.8, 1.2 Hz, 2H, Hg) ppm.
13C NMR (100 MHz, DMSO-d6): : 36.2, 104.1, 116.3, 118.3, 118.8, 124.0, 124.4, 128.3, 129.1, 130.4, 132.2, 140.2, 152.8, 165.1, 166.4 ppm.
3-2-3- ÊјíÈ c3††
7-(4-Bromophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ :Ñä ÑÓæÈ
m.p: 265-267
IR (KBr): 3072 (CH-aromatic), 2935 (CH-aliphatic), 1687 (C=O), 1620, 1485 (C=C), 1195 (C-O), 1043 (C-Br) cm-1.
1H NMR (400 MHz, DMSO-d6): : 6.25 (s, 1H, Ha), 7.08 (d, J = 8.4 Hz, 2H, Hb), 7.28 (t, J = 7.5 Hz, 2H, Hf), 7.31 (d, J = 8.2 Hz, 2H, Hd), 7.37 (d, J = 8.4 Hz, 2H, Hc), 7.56 (dt, J = 7.7, 1.6 Hz, 2H, He), 7.86 (dd, J = 8.0, 1.6 Hz, 2H, Hg) ppm.
13C NMR (100MHz, DMSO-d6): : 36.2, 103.9, 116.2, 118.6, 119.3, 123.8, 124.5, 129.5, 131.1, 131.9,144.3, 152.8, 164.9, 167.0 ppm.
3-2-4- ÊјíÈ d3‡‡
7-(4-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ :Ñä ÑÓæÈ
m.p: >300
IR (KBr): 3060 (CH-aromatic), 2930 (CH-aliphatic), 1660 (C=O), 1610, 1560 (C=C), 1520, 1349 (NO2), 1100 (C-O) cm-1.
1H NMR (400 MHz, DMSO-d6): : 6.35 (s, 1H, Ha), 7.24 (dt, J = 7.5, 1.2 Hz, 2H, Hf), 7.29 (d, J = 8.0 Hz, 2H, Hd), 7.36 (d, J = 8.8 Hz, 2H, Hb), 7.53 (dt, J = 7.6, 1.6 Hz, 2H, He), 7.81 (dd, J = 7.8 Hz, 2H, Hg), 8.06 (d, J = 8.8 Hz, 2H, Hc) ppm.
13C NMR (100 MHz, DMSO-d6): : 37.2, 103.2,116.1,120.0, 123.6, 124.6, 127.6, 128.3, 128.5, 131.7, 145.8, 152.7, 164.8, 168.2 ppm.
3-2-5- ÊјíÈ e3§§
7-(3-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ: Ñä ÑÓæÈ
m.p: 224-226
IR (KBr): 3072 (CH- aromatic), 2939 (CH- aliphatic), 1658, (C=O), 1608, 1564 (C=C), 1529, 1348 (NO2), 1103 (C-O) cm-1.
3-2-6- ÊјíÈ f3***
7-(2-Chlorophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ: Ñä ÑÓæÈ
m.p: 273-275
IR (KBr): 3055 (CH- aromatic), 2945 (CH- aliphatic), 1684 (C=O), 1610, 1402 (C=C), 1188 (C-O), 1074 (C-Cl) cm-1.
3-2- 7- ÊјíÈg3 †††
7-(2-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ:Ñä ÑÓæÈ
m.p: 226-228
IR (KBr): 3074 (CH-aromatic), 2900 (CH-aliphatic), 1652 (C=O), 1610, 1558 (C=C), 1521, 1354 (NO2), 1099 (C-O) cm-1.
3-2-8- ÊјíÈ h3‡‡‡
7-(4-Methoxyphenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ: Ñä ÑÓæÈ
m.p: 238-240
IR (KBr): 3068 (CH- aromatic), 2900 (CH- aliphatic), 1666 (C=O), 1610, 1506 (C=C), 1093 (C-O) cm-1.
3-2-9- ÊјíÈ i3§§§
7-(4-Dimethylamonumphenyl)- 7H-bis-[1] benzo-pyrano [3,4-b:3´,4´-e] pyran-6,8-dione.
ÕæÑÊí: Ñä ÑÓæÈ
m.p: 222-224
IR (KBr): 3041(CH- aromatic), 2918 (CH- aliphatic), 1677 (C=O), 1610, 1400 (C=C), 1093 (C-O) cm-1.
3-2-10- ÊјíÈ j3****
7-(Phenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÓÝíÏ : Ñä ÑÓæÈ
m.p: 200-203
IR (KBr): 3062 (CH-aromatic), 2939 (CH-aliphatic), 1672 (C=O), 1608, 1492 (C=C), 1099 (C-O) cm-1.
ÝÕá åÇÑã
ØíÝ åÇ
ÊјíÈ a3
7-(3-Bromophenyl)-7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(3-Bromophenyl)-7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(3-Bromophenyl)-7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(3-Bromophenyl)-7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(3-Bromophenyl)-7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ b3
7-(4-Chlorophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
-(4-Chlorophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Chlorophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Chlorophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ c3
7-(4-Bromophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Bromophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Bromophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Bromophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Bromophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ d3
7-(4-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
7-(4-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione
.
7-(4-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ e3
7-(3-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ f3
7-(2-Chlorophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ g3
7-(2-Nitrophenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.

ÊјíÈ h3
7-(4-Methoxyphenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ i3
7-(4-Dimethylamonumphenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ÊјíÈ j3
7-(Phenyl)- 7H-bis-[1] benzo-pyrano[3,4-b:3´,4´-e] pyran-6,8-dione.
ãÑÇÌÚ
Reference:
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Abstract:
Pyrans are an important group of organic compounds that have various biological and pharmacological properties and they are used in producing of peptides like fungus insecticides, antivirus, and antiseizure drugs.
In this study, for the first time, bis-benzo-pyrano pyran- 6,8 dione derivatives produced by one- pot three- component condensation of 4- hydroxy coumarin with various aromatic aldehydes in the presence of sodium diphenyl amin-4-solfunate as effective catalyst under mild condition. The products were obtained at a short time and high yield.
Keywords: 4-Hydroxy coumarin, Aldehyde, Bis-benzo-pyrano pyran-6,8 dione, Sodium diphenyl amine-4-solfunate
1 . Silica- bonded N-propylpiperazine sodium N-propionat
2 . Silica- bonded N-propylpiperazine
3 . Tetrabutylammonim Hexatungstate
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قیمت: تومان


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