1-naphthylmethyl 3α,12α-bis(chloroacetyloxy)-5β-cholan-24-oate | 875341-39-2

• 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,12α-bis(chloroacetyloxy)-5β-cholan-24-oate
• 英文别名: naphthalen-1-ylmethyl (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]pentanoate
• CAS: 875341-39-2
• 化学式: C₃₉H₅₀Cl₂O₆
• 分子量: 685.728
• InChiKey: HAMURXDIWGPFJI-BIWXRCBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-naphthylmethyl 3α,12α-bis(chloroacetyloxy)-5β-cholan-24-oate 、 sodium cholate 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以86%的产率得到[2-[[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-12-[2-[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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]oxyacetyl]oxy-10,13-dimethyl-17-[(2R)-5-(naphthalen-1-ylmethoxy)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethyl] (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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
  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 deoxycholate 在 calcium hydride 、 苄基三乙基氯化铵 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以86%的产率得到1-naphthylmethyl 3α,12α-bis(chloroacetyloxy)-5β-cholan-24-oate
  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

• 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.