1-naphthylmethyl 3α,7α,12α-tris(chloroacetyloxy)-5β-cholan-24-oate | 875341-40-5

• 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: 1-naphthylmethyl 3α,7α,12α-tris(chloroacetyloxy)-5β-cholan-24-oate
• 英文别名: naphthalen-1-ylmethyl (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]pentanoate
• CAS: 875341-40-5
• 化学式: C₄₁H₅₁Cl₃O₈
• 分子量: 778.21
• InChiKey: KGRVKBXBARUWDM-COVZNTEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-naphthylmethyl 3α,7α,12α-tris(chloroacetyloxy)-5β-cholan-24-oate 、 sodium cholate 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到
  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：

  氯乙酰氯 、 1-Naphthylmethyl cholate 在 苄基三乙基氯化铵 作用下， 以 甲苯 为溶剂， 以80%的产率得到1-naphthylmethyl 3α,7α,12α-tris(chloroacetyloxy)-5β-cholan-24-oate
  参考文献：
  名称：

  胆酸低聚物-牛磺酸结合物的合成：它们的聚集和胆固醇增溶研究

  摘要：

  合成了胆酸单元之间具有不同间隔物的两种胆酸衍生的低聚物的牛磺酸缀合物。这些分子在水性介质中自组装。通过使用荧光光谱分析测量临界胶束浓度 (CMC) 值，并通过动态光散射和电子显微镜表征聚集体。研究了这些四聚体中胆酸单元对溶解胆固醇的协同作用。还研究了这些分子作为亲脂性染料的纳米载体的能力。

  DOI：

  10.1002/ejoc.201200312

文献信息

• Synthesis of Cholic Acid Oligomer-Taurine Conjugates: A Study of Their Aggregation and Cholesterol Solubilization
  作者：T. B. N. Satyanarayana、Uday Maitra、A. J. Savyasachi

  DOI：10.1002/ejoc.201200312

  日期：2012.7

  Taurine conjugates of two cholic acid derived oligomers with different spacers between the cholic acid units were synthesized. These molecules self-assemble in aqueous media. The critical micelle concentration (CMC) values were measured by using fluorescence spectroscopic analysis and the aggregates were characterized by dynamic light scattering and electron microscopy. The cooperativity of the cholic

  合成了胆酸单元之间具有不同间隔物的两种胆酸衍生的低聚物的牛磺酸缀合物。这些分子在水性介质中自组装。通过使用荧光光谱分析测量临界胶束浓度 (CMC) 值，并通过动态光散射和电子显微镜表征聚集体。研究了这些四聚体中胆酸单元对溶解胆固醇的协同作用。还研究了这些分子作为亲脂性染料的纳米载体的能力。
• 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.