7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester | 134005-68-8

• 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)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
• CAS: 134005-68-8
• 化学式: C₃₃H₆₂O₅Si₂
• 分子量: 595.023
• InChiKey: LXPDZVODIHPEMK-UIRWWBRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.07
• 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：
  0.88
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester 在 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 生成 methyl 3(R)-hydroxy-2β-(3(S)-hydroxy-1-octynyl)-5-oxocyclopentane-1α-heptanoate
  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：

  (3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-[(3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-ynyl]-2-methylidenecyclopentan-1-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-ynyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
  参考文献：
  名称：

  Highly efficient synthesis of 13-dehydroprostaglandins by 1,4-addition reaction of alkynyl .omega. side-chain unit onto a cyclopentenone framework

  摘要：

  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.

  DOI：

  10.1021/jo00010a004