3α,7α,12α-tris(chloroacetyloxy)-5β-cholanic acid

• 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: 3α,7α,12α-tris(chloroacetyloxy)-5β-cholanic acid
• 英文别名: (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris[(2-chloroacetyl)oxy]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• 化学式: C₃₀H₄₃Cl₃O₈
• 分子量: 638.026
• InChiKey: MHCKTPNZGAJZKB-RLONDOPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3α,7α,12α-tris(chloroacetyloxy)-5β-cholanic acid 在 COCl₂ 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  基于胆汁酸的树突状光收集系统的简单构造。

  摘要：

  [结构：见正文]报道了一种由9个萘普生和一个蒽标记的胆酸衍生的树枝状结构的合成方法。这种多色，新颖的树枝状结构可作为有效的分子光收集器。

  DOI：

  10.1021/ol050809m
• 作为产物：
  描述：

  胆酸 、 氯乙酸酐 在 吡啶 作用下， 反应 0.75h， 以79%的产率得到3α,7α,12α-tris(chloroacetyloxy)-5β-cholanic acid
  参考文献：
  名称：

  Hydroxyl-Terminated Dendritic Oligomers from Bile Acids:  Synthesis and Properties

  摘要：

  [GRAPHICS]The high reactivity of the chloroacetyl group has been exploited for the synthesis of bile acid based first and second generation dendrons with multiple hydroxyl groups. The synthesis involves only a few steps and avoids the use of protecting groups for the terminal hydroxyl groups. These dendritic structures with facially amphiphilic bile acid backbones on the periphery were able to solubilize cresol red, a hydrophilic dye, in a nonpolar solvent. HPLC analysis of the dendrons suggests that hydrophobicity increases with increase in oligomer size, but in each generation, the dendrons with a higher degree of branching are less hydrophobic.

  DOI：

  10.1021/jo052173i

文献信息

• A Simple Construction of a Bile Acid Based Dendritic Light Harvesting System
  作者：N. Vijayalakshmi、Uday Maitra

  DOI：10.1021/ol050809m

  日期：2005.6.1

  [structure: see text] A facile synthesis of a cholic acid derived dendritic structure labeled with nine naproxens and a single anthracene is reported. This multichromophoric, novel dendritic construct acts as an efficient molecular light harvester.

  [结构：见正文]报道了一种由9个萘普生和一个蒽标记的胆酸衍生的树枝状结构的合成方法。这种多色，新颖的树枝状结构可作为有效的分子光收集器。
• Hydroxyl-Terminated Dendritic Oligomers from Bile Acids:  Synthesis and Properties
  作者：N. Vijayalakshmi、Uday Maitra

  DOI：10.1021/jo052173i

  日期：2006.1.1

  [GRAPHICS]The high reactivity of the chloroacetyl group has been exploited for the synthesis of bile acid based first and second generation dendrons with multiple hydroxyl groups. The synthesis involves only a few steps and avoids the use of protecting groups for the terminal hydroxyl groups. These dendritic structures with facially amphiphilic bile acid backbones on the periphery were able to solubilize cresol red, a hydrophilic dye, in a nonpolar solvent. HPLC analysis of the dendrons suggests that hydrophobicity increases with increase in oligomer size, but in each generation, the dendrons with a higher degree of branching are less hydrophobic.