lithocholic acid ethane-1,2-diol diester | 181633-75-0

• 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: lithocholic acid ethane-1,2-diol diester
• 英文别名: 2-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-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)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 181633-75-0
• 化学式: C₅₀H₈₂O₆
• 分子量: 779.197
• InChiKey: RGXXHDDEOQSNJN-AJEPHTPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  lithocholic acid ethane-1,2-diol diester 、 邻乙酰水杨酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 120.0h， 以2.5%的产率得到3α,3'α-bis(2-acetoxyphenylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol
  参考文献：
  名称：

  3α,3′α-Bis(n-acetoxyphenylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol diesters (n = 2-4):13C NMR chemical shifts, variable-temperature and NOE1H NMR measurements and MO calculations of novel bile acid-based dimers

  摘要：

  Three novel bile acid-based molecular dimers, 3 alpha,3'alpha-bis(n -acetoxyphenylcarboxy)-5 beta-cholan-24-oic acid ethane-1,2-diol diesters (n = 2-4), 1-3, were synthesized from lithocholic acid (3 alpha-hydroxy-5 beta-cholan-24-oic acid) ethane-1,2-diol diester and isomeric n-acetoxybenzoyl chlorides (n = 2-4). Their cleft-type conformational preferences were suggested theoretically by PM3 molecular orbital calculations. Molecular weights determined by the matrix-assisted laser desorption/ionization time-of-flight technique and C-13 NMR chemical shifts of the 1-3 are also presented. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1097-458x(200010)38:10<877::aid-mrc750>3.0.co;2-2
• 作为产物：
  描述：

  石胆酸 在 吡啶 、 氯化亚砜 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 为溶剂， 反应 52.25h， 生成 lithocholic acid ethane-1,2-diol diester
  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

• Tamminen, Jari; Lappalainen, Kari; Laihia, Katri, Magnetic Resonance in Chemistry, 1999, vol. 37, # 2, p. 163 - 165
  作者：Tamminen, Jari、Lappalainen, Kari、Laihia, Katri、Maenttaeri, Pia、Salo, Hannu、Kolehmainen, Erkki

  DOI：——

  日期：——
• 3α,3′α-Bis(n-acetoxyphenylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol diesters (n = 2-4):13C NMR chemical shifts, variable-temperature and NOE1H NMR measurements and MO calculations of novel bile acid-based dimers
  作者：Jari Tamminen、Erkki Kolehmainen、Juha Linnanto、Hannu Salo、Pia Mänttäri

  DOI：10.1002/1097-458x(200010)38:10<877::aid-mrc750>3.0.co;2-2

  日期：2000.10

  Three novel bile acid-based molecular dimers, 3 alpha,3'alpha-bis(n -acetoxyphenylcarboxy)-5 beta-cholan-24-oic acid ethane-1,2-diol diesters (n = 2-4), 1-3, were synthesized from lithocholic acid (3 alpha-hydroxy-5 beta-cholan-24-oic acid) ethane-1,2-diol diester and isomeric n-acetoxybenzoyl chlorides (n = 2-4). Their cleft-type conformational preferences were suggested theoretically by PM3 molecular orbital calculations. Molecular weights determined by the matrix-assisted laser desorption/ionization time-of-flight technique and C-13 NMR chemical shifts of the 1-3 are also presented. Copyright (C) 2000 John Wiley & Sons, Ltd.
• 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。