(Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(4-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester | 62525-20-6

• 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: (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(4-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester
• CAS: 62525-20-6
• 化学式: C₄₄H₅₉ClO₉Se
• 分子量: 846.36
• InChiKey: QXZPPNSYDDXETD-DUQNNVFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  55.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(4-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester 在 双氧水 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 0.33h， 以85%的产率得到(2E,5Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(4-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,5-dienoic acid 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
• 作为产物：
  描述：

  methyl (Z)-7-((1R,2S,3R,5S)-5-acetoxy-2-(((2-methoxypropan-2-yl)oxy)methyl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate 在 盐酸 、 sodium tetrahydroborate 、 pyridine-SO3 complex 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 7.75h， 生成 (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(4-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid 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