16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F1α 11,15αβ-bis(tetrahydropyran-2-yl ether) | 73275-80-6

• 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-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F1α 11,15αβ-bis(tetrahydropyran-2-yl ether)
• 英文别名: 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F_1α 11,15αβ-bis(tetrahydropyran-2-yl ether)
• CAS: 73275-80-6
• 化学式: C₃₃H₄₃F₃O₈
• 分子量: 624.695
• InChiKey: YQHTUHRDYZZHAT-IGQBBJRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  103.68
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F1α 11,15αβ-bis(tetrahydropyran-2-yl ether) 在 Pd-BaSO₄ 吡啶 、 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E)-(S)-3-hydroxy-4-(3-trifluoromethyl-phenoxy)-but-1-enyl]-cyclopentyl}-hept-2-enoic acid
  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：

  5-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-4-(3-trifluoromethyl-phenoxy)-but-1-enyl]-cyclopentyl}-pentanoic acid 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.08h， 生成 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F1α 11,15αβ-bis(tetrahydropyran-2-yl ether)
  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