16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F_1α methyl ester | 68399-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F_1α methyl ester
• 英文别名: methyl (2E,5E)-7-[(1R,2R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hepta-2,5-dienoate
• CAS: 68399-12-2
• 化学式: C₂₃H₂₉ClO₆
• 分子量: 436.933
• InChiKey: FNAMRDZHKYQEBA-XPSLYBKESA-N

物化性质

• 沸点：
  592.6±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 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 、 双氧水 、 对甲苯磺酸 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 24.24h， 生成 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin 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

文献信息

• Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain
  作者：Masaki Hayashi、Yoshinobu Arai、Hirohisa Wakatsuka、Masanori Kawamura、Yoshitaka Konishi、Takeshi Tsuda、Kimiichiro Matsumoto

  DOI：10.1021/jm00179a011

  日期：1980.5

  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.