methyl 3(R)-hydroxy-2β-(3(S)-hydroxy-1-octynyl)-5-oxocyclopentane-1α-heptanoate | 64130-17-2

• 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: methyl 3(R)-hydroxy-2β-(3(S)-hydroxy-1-octynyl)-5-oxocyclopentane-1α-heptanoate
• 英文别名: methyl 7-[(1R,2S,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-ynyl]-5-oxocyclopentyl]heptanoate
• CAS: 64130-17-2
• 化学式: C₂₁H₃₄O₅
• 分子量: 366.498
• InChiKey: JBKBHSPVIDVXHR-JRBPQWBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3(R)-hydroxy-2β-(3(S)-hydroxy-1-octynyl)-5-oxocyclopentane-1α-heptanoate 在 porcine liver esterase 、 phosphate buffer 作用下， 生成 3(R)-hydroxy-2β-(3(S)-hydroxy-1-octynyl)-5-oxocyclopentane-1α-heptanoic acid
  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 、 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

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.
• US3970683A
  申请人：——

  公开号：US3970683A

  公开（公告）日：1976-07-20