methyl (R)-4-((3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-(adamantan-1-yl)acetamido)-7,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate | 1209000-29-2

• 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: methyl (R)-4-((3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-(adamantan-1-yl)acetamido)-7,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
• CAS: 1209000-29-2
• 化学式: C₃₇H₅₉NO₅
• 分子量: 597.879
• InChiKey: LXSJTLKEVNURIU-ORLNIUSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  95.86
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (R)-4-((3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-(adamantan-1-yl)acetamido)-7,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以90%的产率得到[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
• 作为产物：
  描述：

  1-金刚烷乙酰氯 、 (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid methyl ester 在 三乙胺 作用下， 以 氯仿 为溶剂， 以40%的产率得到methyl (R)-4-((3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-(adamantan-1-yl)acetamido)-7,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
  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