3-Iodo-benzoic acid (3R,5S,8S,9R,10S,13S,14S,16R,17S)-17-acetyl-9-chloro-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester | 96354-44-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-Iodo-benzoic acid (3R,5S,8S,9R,10S,13S,14S,16R,17S)-17-acetyl-9-chloro-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester
• CAS: 96354-44-8
• 化学式: C₂₈H₃₄ClIO₄
• 分子量: 596.933
• InChiKey: JBXRISDADPTLDU-WUDBRHHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.9
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Iodo-benzoic acid (3R,5S,8S,9R,10S,13S,14S,16R,17S)-17-acetyl-9-chloro-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 生成 1-((3R,5S,8S,10S,13S,14S,16R,17S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,10,12,13,14,15,16-tetradecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-17-yl)-ethanone
  参考文献：
  名称：

  An efficient synthesis of 3α-hydroxy-5α-pregna-9(11),16-diene-20-one

  摘要：

  3 alpha-Hydroxy-5 alpha-pregna-9(11),16-diene-20-one (6) was synthesized for the first time from the commercially available 16,17 alpha-epoxy-3 beta-hydroxy-5-pregnen-20-one(1) in several steps. The key step involves a remote chlorination reaction utilizing m-iodobenzoate group as a free-radical guide.

  DOI：

  10.1016/s0039-128x(84)90120-x
• 作为产物：
  描述：

  (3β,5α,16α)-16,17-epoxy-3-hydroxypregnan-20-one 在 2,3-二氯碘苯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-Iodo-benzoic acid (3R,5S,8S,9R,10S,13S,14S,16R,17S)-17-acetyl-9-chloro-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  An efficient synthesis of 3α-hydroxy-5α-pregna-9(11),16-diene-20-one

  摘要：

  3 alpha-Hydroxy-5 alpha-pregna-9(11),16-diene-20-one (6) was synthesized for the first time from the commercially available 16,17 alpha-epoxy-3 beta-hydroxy-5-pregnen-20-one(1) in several steps. The key step involves a remote chlorination reaction utilizing m-iodobenzoate group as a free-radical guide.

  DOI：

  10.1016/s0039-128x(84)90120-x