[3β,5β,7α,12α]-3-[(adamantyl-1-acetyl)amino]-7,12-dihydroxycholan-24-oic acid | 1209000-30-5

• 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: [3β,5β,7α,12α]-3-[(adamantyl-1-acetyl)amino]-7,12-dihydroxycholan-24-oic acid
• 英文别名: (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[2-(1-adamantyl)acetyl]amino]-7,12-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]pentanoic acid
• CAS: 1209000-30-5
• 化学式: C₃₆H₅₇NO₅
• 分子量: 583.852
• InChiKey: SOASPIYLRFMBBI-DLZVXUOWSA-N

物化性质

• 沸点：
  756.3±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-金刚烷乙酸 在 氯化亚砜 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.0h， 生成 [3β,5β,7α,12α]-3-[(adamantyl-1-acetyl)amino]-7,12-dihydroxycholan-24-oic acid
  参考文献：
  名称：

  Enantioresolution and Chameleonic Mimicry of 2-Butanol with an Adamantylacetyl Derivative of Cholic Acid

  摘要：

  [3 beta,5 beta,7 alpha,12 alpha]-3[(Adamantyl-1-acetyl)-amino]-7-12-dihydroxycholan-24-oic acid (AdCH(2)CA) was synthesized by the reaction between 1-adamantyl acetyl chloride and the methyl ester of 3 beta-amino-cholic acid and hydrolysis of the ester. The acid wits recrystallized from racemic 2-butanol (0.1 % water). Crystals are orthorhombic (P2(1)2(1)2(1)) and form inclusion complexes with water and 2-butanol with a 1:1:1 stoichiometry. Only the S-enantiomer is included into the structure of the crystal, exhibiting a chameleonic mimicry with the steroid bilayers. The isolation of crystals allows the enantioresolution of the racemate with a high purity (approximate to 99%) of S-2-butanol. The steroid molecules are disposed in an antiparallel orientation in the hydrophobic layer and it parallel orientation in the hydrophilic one.

  DOI：

  10.1021/cg9009064