16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester | 69222-87-3

• 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: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester
• 英文别名: methyl (E)-7-[(1R,2R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
• CAS: 69222-87-3
• 化学式: C₂₃H₃₁ClO₆
• 分子量: 438.949
• InChiKey: DVBATKLFQCCUII-GQOWFAAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  96.22
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 生成 methyl 7-[2-[4-(3-chlorophenoxy)-3-(oxan-2-yloxy)but-1-enyl]-3,5-bis(oxan-2-yloxy)cyclopentyl]-2-phenylselanylhept-5-enoate
  参考文献：
  名称：

  Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain

  摘要：

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.

  DOI：

  10.1021/jm00179a011
• 作为产物：
  描述：

  methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate 在 二苯硫醚 作用下， 以 甲醇 、 苯 为溶剂， 反应 22.0h， 以61%的产率得到16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester
  参考文献：
  名称：

  Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain

  摘要：

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.

  DOI：

  10.1021/jm00179a011