Acetic acid (3R,5R,6S,8S,9S,10R,13R,14S,17R)-3-acetoxy-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester | 67371-35-1

• 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: Acetic acid (3R,5R,6S,8S,9S,10R,13R,14S,17R)-3-acetoxy-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester
• 英文别名: (3I+/-,5I(2),6I+/-)-3,6-Bis(acetyloxy)cholan-24-oyl chloride；[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-6-acetyloxy-17-[(2R)-5-chloro-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 67371-35-1
• 化学式: C₂₈H₄₃ClO₅
• 分子量: 495.099
• InChiKey: LQGWBODUBULJPH-FXFOLUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,5R,6S,8S,9S,10R,13R,14S,17R)-3-acetoxy-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester 在 吡啶 、 氢氧化钾 、 potassium acetate 、 lithium chloride 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 24-oxocholesterol
  参考文献：
  名称：

  Synthesis of desmosterol and epidesmosterol from hyodeoxycholic acid

  摘要：

  A new synthesis of desmosterol was described using hyodeoxycholic acid (3alpha,6alpha-dihydroxy-5beta-cholanic acid) as a starting material. Epidesmosterol (3alpha-hydroxycholesta-5,24-diene) was also synthesized for the first time from the same starting material.

  DOI：

  10.1016/s0039-128x(77)80025-1
• 作为产物：
  描述：

  3α,6α-diacetoxy-5β-cholan-24-oic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Acetic acid (3R,5R,6S,8S,9S,10R,13R,14S,17R)-3-acetoxy-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester
  参考文献：
  名称：

  Synthesis and antifungal activity of bile acid-derived oxazoles

  摘要：

  Peracetylated bile acids (1a-g) were used as starting materials for the preparation of fourteen new derivatives bearing an oxazole moiety in their side chain (6a-g, 8a-g). The key step for the synthetic path was a Dakin-West reaction followed by a Robinson-Gabriel cyclodehydration. A simpler model oxazole (12) was also synthesized. The antifungal activity of the new compounds (6a-g) as well as their starting bile acids (1a-g) was tested against Candida albicans. Compounds 6e and 6g showed the highest percentages of inhibition (63.84% and 61.40% at 250 mu g/mL respectively). Deacetylation of compounds 6a-g, led to compounds 8a-g which showed lower activities than the acetylated derivatives. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.01.014

文献信息

• (Trifluoroisopropenyl)tributyltin as a Novel .alpha.-(Trifluoromethyl)ethenyl Carbanion Synthetic Equivalent. Preparation and Its Palladium-Promoted Coupling with Acyl Chlorides
  作者：Yuanyao Xu、Fuqiang Jin、Weiyuan Huang

  DOI：10.1021/jo00088a061

  日期：1994.5