7-{(1R,2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester | 134005-69-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-{(1R,2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester
• CAS: 134005-69-9
• 化学式: C₃₃H₆₄O₅Si₂
• 分子量: 597.039
• InChiKey: CJYVSCURGSEVQA-NAGJOQLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.86
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-{(1R,2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester 在 lithium hydroxide 、 氢氟酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 13,14-Didehydro-PGF(1α)
  参考文献：
  名称：

  Synthesis and pharmacological activities of 13-Dehydro derivatives of primary prostaglandins

  摘要：

  13-Dehydro derivatives of prostaglandin E-1, E-2, E-3, F-1 alpha, and F-2 alpha were synthesized. Compared with natural prostaglandins, 13-dehydro analogues were found to exhibit more potent inhibitory activity against human platelet aggregation and relaxation of guinea-pig isolated trachea, while they showed less potent activity of contraction of guinea-pig isolated ileum. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00247-9
• 作为产物：
  描述：

  iodozinc(1+),methyl hexanoate 在 盐酸 、 三甲基氯硅烷 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 生成 7-{(1R,2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and pharmacological activities of 13-Dehydro derivatives of primary prostaglandins

  摘要：

  13-Dehydro derivatives of prostaglandin E-1, E-2, E-3, F-1 alpha, and F-2 alpha were synthesized. Compared with natural prostaglandins, 13-dehydro analogues were found to exhibit more potent inhibitory activity against human platelet aggregation and relaxation of guinea-pig isolated trachea, while they showed less potent activity of contraction of guinea-pig isolated ileum. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00247-9

文献信息

• Highly efficient synthesis of 13-dehydroprostaglandins by 1,4-addition reaction of alkynyl .omega. side-chain unit onto a cyclopentenone framework
  作者：Toshiharu Yoshino、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/jo00010a004

  日期：1991.5

  Optically active 2-((diethylamino)methyl)-4-siloxy-2-cyclopentenone (2) reacts with a diethyl(3-(tert-butyldimethylsiloxy)-1-alkynyl) aluminum compound via 1,4-addition pathway to afford the enone 5, useful intermediate for synthesis of PGs via two-component coupling process, in excellent yield, thus making it easy to synthesize 13-dehydro-PGs.