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恩前列素

恩前列素

CAS号：73121-56-9

英文名：methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate

分子式

C23H28O6

熔点

密度

1.201g/cm3

分子量

400.465

沸点

552.9ºC at 760 mmHg

溶解度

信号词

危险品标志

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化合物简介

Enprostil is a synthetic analogue of prostaglandin E2 and was found to be effective in the treatment of patients with duodenal or gastric ulcers.

基本信息

中文名称

恩前列素

英文名称

methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate

中文别名

恩前列腺素、[1Α,2Β(1E,3R^^),3Α]-7-[-3-羟基-2-(-3-羟基-4-苯氧基-1-丁烯基)-5-氧环戊基]-4,5-庚二烯酸甲酯

英文别名

Camleed、enprostil、Enprostil (JAN/USAN/INN)、methyl (4,5,6R)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate、Syngard、Gardrine、methyl (4,5,6S)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate、Camleed (TN)

CAS号

73121-56-9

分子式

C23H28O6

分子量

400.465

精确质量

400.189

PSA

93.06

LOGP

2.6032

编号系统

UNII

J4IP5Z9DAU

物化性质

密度

1.201g/cm3

沸点

552.9ºC at 760 mmHg

闪点

185.7ºC

折射率

1.586

生产方法及用途

生产方法

化合物(Ⅰ)先经硅烷化，再氧化，然后脱硅烷基，得到恩前列素。

用途

为合成的去氢PGE2，能抑制动物和人体的基础胃酸和由组胺、五肽胃泌素、食物等引起的胃酸分泌。用于胃炎、胃溃疡及十二指肠溃疡。

合成路线

(-)-11α,15α-bis((tert-butyldimethylsilyl)oxy)-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

(-)-11α,15α-bis((tert-butyldimethylsilyl)oxy)-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

恩前列素

上游原料

共找到6个上游原料 >

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone

(3aR,4R,5R,6aS)-4-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol

(3aR,4R,5R,6aS)-4-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol

(-)-11α,15α-bis((tert-butyldimethylsilyl)oxy)-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

(-)-11α,15α-bis((tert-butyldimethylsilyl)oxy)-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

1-[5α-hydroxy-2β-[(E)-4-phenoxy-3α-tetrahydropyran-2-yloxy-1-butenyl]-3α-tetrahydropyran-2-yloxycyclopent-1α-yl]but-3-yn-2-ol

1-[5α-hydroxy-2β-[(E)-4-phenoxy-3α-tetrahydropyran-2-yloxy-1-butenyl]-3α-tetrahydropyran-2-yloxycyclopent-1α-yl]but-3-yn-2-ol

(3aR,4R,5R,6aS)-Hexahydro-4-[(E)-(3R)-4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-Hexahydro-4-[(E)-(3R)-4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one

(R)-3-((tert-butyldimethylsilyl)oxy)-4-phenoxy-1-butyne

(R)-3-((tert-butyldimethylsilyl)oxy)-4-phenoxy-1-butyne

上游原料

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone (3aR,4R,5R,6aS)-4-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol (-)-11α,15α-bis((tert-butyldimethylsilyl)oxy)-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester 1-[5α-hydroxy-2β-[(E)-4-phenoxy-3α-tetrahydropyran-2-yloxy-1-butenyl]-3α-tetrahydropyran-2-yloxycyclopent-1α-yl]but-3-yn-2-ol (3aR,4R,5R,6aS)-Hexahydro-4-[(E)-(3R)-4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one (R)-3-((tert-butyldimethylsilyl)oxy)-4-phenoxy-1-butyne