2-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxyethyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate | 181633-74-9

• 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: 2-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxyethyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 181633-74-9
• 化学式: C₅₄H₈₀F₆O₈
• 分子量: 971.215
• InChiKey: NZOHNMQRPCPCHK-ZMQYMIQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  68
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxyethyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate 在 4-二甲氨基吡啶 、 碳酸氢钠 、 2,6-二氯苯甲酰氯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 43.0h， 生成 cholaphane
  参考文献：
  名称：

  Substituted Methyl 5β-Cholan-24-oates; Part III: Synthesis of a Novel Cholaphane from Ethylene Glycol Diester of Lithocholic Acid by Cyclization with Terephthalic Acid

  摘要：

  一种新型的cholaphane，含有脂肪族和芳香族间隔基，由3α-羟基-5β-cholan-24-oic 酸（石胆酸）的乙二醇二酯通过对苯二甲酸环化（山口法）制备而成。

  DOI：

  10.1055/s-1996-4338
• 作为产物：
  描述：

  石胆酸 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 49.25h， 生成 2-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxyethyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(2,2,2-trifluoroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  Substituted Methyl 5β-Cholan-24-oates; Part III: Synthesis of a Novel Cholaphane from Ethylene Glycol Diester of Lithocholic Acid by Cyclization with Terephthalic Acid

  摘要：

  一种新型的cholaphane，含有脂肪族和芳香族间隔基，由3α-羟基-5β-cholan-24-oic 酸（石胆酸）的乙二醇二酯通过对苯二甲酸环化（山口法）制备而成。

  DOI：

  10.1055/s-1996-4338

文献信息

• Substituted Methyl 5β-Cholan-24-oates; Part III: Synthesis of a Novel Cholaphane from Ethylene Glycol Diester of Lithocholic Acid by Cyclization with Terephthalic Acid
  作者：Erkki Kolehmainen、Jari Tamminen、Kari Lappalainen、Tuire Torkkel、Raimo Seppälä

  DOI：10.1055/s-1996-4338

  日期：1996.9

  A novel cholaphane, containing both an aliphatic and an aromatic spacer, has been prepared from ethylene glycol diester of 3α-hydroxy-5β-cholan-24-oic acid (lithocholic acid) by cyclization (Yamaguchi method) with terephthalic acid.

  一种新型的cholaphane，含有脂肪族和芳香族间隔基，由3α-羟基-5β-cholan-24-oic 酸（石胆酸）的乙二醇二酯通过对苯二甲酸环化（山口法）制备而成。