(R)-3-((5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-butyric acid methyl ester | 61844-73-3

• 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: (R)-3-((5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-butyric acid methyl ester
• CAS: 61844-73-3
• 化学式: C₂₄H₃₈O₅
• 分子量: 406.563
• InChiKey: DVJLKORIYFJIBP-DXTOHYNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-3-((5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-butyric acid methyl ester 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 methyl (3R)-3-[(3S,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanoate
  参考文献：
  名称：

  Bile acids. LII. The synthesis of 24-nor-5α-cholic acid and its 3β-isomer

  摘要：

  To aid in the identification of trihydroxy acidic metabolite(s) derived from beta-sitosterol, 3alpha,7alpha,12alpha-trihydroxy-24-nor-5beta-cholan-23-oic acid was prepared and its methyl ester was treated with Raney nickel in boiling p-cymene to provide methyl 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5alpha-cholanate, 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5beta-cholante and 3-oxo-7alpha,12alpha-dihydroxy-24-norchol-4-enoate. The latter compound was synthesized from the 3-oxo-5beta-derivative with SeO2 to provide a product with identical properties. Catalytic reduction of either saturated 3-oxo-derivative provided the appropriate 3,7,12-triols isomeric at C-3. Results from gas liquid and partition chromatography, mass spectrometry, and otherr physical properties of the acids, their methyl esters and other derivatives are compatible with the assigned structures.

  DOI：

  10.1016/0039-128x(76)90007-6
• 作为产物：
  描述：

  胆酸甲酯 在 镍 4-异丙基甲苯 、 碳酸氢钠 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 (R)-3-((5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Bile acids. LII. The synthesis of 24-nor-5α-cholic acid and its 3β-isomer

  摘要：

  To aid in the identification of trihydroxy acidic metabolite(s) derived from beta-sitosterol, 3alpha,7alpha,12alpha-trihydroxy-24-nor-5beta-cholan-23-oic acid was prepared and its methyl ester was treated with Raney nickel in boiling p-cymene to provide methyl 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5alpha-cholanate, 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5beta-cholante and 3-oxo-7alpha,12alpha-dihydroxy-24-norchol-4-enoate. The latter compound was synthesized from the 3-oxo-5beta-derivative with SeO2 to provide a product with identical properties. Catalytic reduction of either saturated 3-oxo-derivative provided the appropriate 3,7,12-triols isomeric at C-3. Results from gas liquid and partition chromatography, mass spectrometry, and otherr physical properties of the acids, their methyl esters and other derivatives are compatible with the assigned structures.

  DOI：

  10.1016/0039-128x(76)90007-6