3α,12α-bis(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,12α-bis(chloroacetyloxy)-5β-cholanic acid
• 英文别名: (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-bis[(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: C₂₈H₄₂Cl₂O₆
• 分子量: 545.544
• InChiKey: PMUWUZADCAAAHK-CNZWOIIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3α,12α-bis(chloroacetyloxy)-5β-cholanic acid 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成
  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
• 作为产物：
  描述：

  去氧胆酸 、 氯乙酸酐 在 吡啶 作用下， 反应 0.75h， 以75%的产率得到3α,12α-bis(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

• Synthesis and optimization of stapled DOCK peptides with improved drug-like properties
  作者：Atiruj Theppawong、Ewout De Geyter、Annemieke Madder

  DOI：10.24820/ark.5550190.p012.170

  日期：——