methyl 3-oxo-7α-hydroxy-5β-cholane-24-carboxylate | 80722-55-0

• 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 3-oxo-7α-hydroxy-5β-cholane-24-carboxylate
• CAS: 80722-55-0
• 化学式: C₂₆H₄₂O₄
• 分子量: 418.617
• InChiKey: WUVQMHHIIYCHLV-ZTMFVMPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-oxo-7α-hydroxy-5β-cholane-24-carboxylate 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 生成 3-oxo-4,6-choladiene-24-carboxylic acid
  参考文献：
  名称：

  Bile acids. LXXIII. Synthesis of analogs of 7α-hydroxy-4-cholesten-3-one as substrates for hepatic steroid 12α-hydroxylase

  摘要：

  Analogs of 7 alpha-hydroxy-4-cholesten-3-one were prepared to ascertain structural features necessary for maximal activity of hepatic microsomal 12 alpha-steroid hydroxylase. Methyl 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24-carboxylate derived from chenodeoxycholic acid was oxidized at C-3 with silver carbonate/Celite. The product was hydrolyzed and dehydrogenated with SeO2 to provide 3-oxo-7 alpha-hydroxy-4-cholene-24-carboxylic acid. 5 beta-Cholestane-3 alpha,7 alpha,25-triol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol were similarly oxidized at C-3 and dehydrogenated to provide 7 alpha,25-dihydroxy-4-cholesten-3-one and 7 alpha,12 alpha,25-trihydroxy-4-cholesten-3-one, respectively. The products were characterized by thin-layer and gas chromatography, ultraviolet, infrared, proton resonance and mass spectrometry.

  DOI：

  10.1016/s0039-128x(84)80020-3
• 作为产物：
  描述：

  (5R)-5-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-二羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]己酸 在 盐酸 、 4-异丙基甲苯 、 镍 、 2,2-二甲氧基丙烷 作用下， 反应 2.0h， 生成 methyl 3-oxo-7α-hydroxy-5β-cholane-24-carboxylate
  参考文献：
  名称：

  Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids

  摘要：

  Interest in the structural requirements of a sterol or bile acid for maximal activity by an hepatic microsomal steroid 12 alpha-hydroxylase prompted the preparation of 5 alpha-cholestane-3 alpha, 7 alpha, 25-triol and 5 alpha-analogs of 3 alpha, 7 alpha-dihydroxy-5 beta-cholane-24-carboxylic acid. Methyl 3 alpha, 7 alpha-dihydroxy-5 beta-cholane-24-carboxylate derived from methyl chenodeoxycholate via the Arndt-Eistert reaction was allomerized with Raney nickel in boiling p-cymene to provide a number of product of which methyl 3, 7-dioxo-5 beta- and 5 alpha-cholane-24-carboxylates, methyl 3-oxo-7 alpha-hydroxy-5 beta-and 5 alpha-cholane-24-carboxylates, were identified. Reduction with K-Selectride of methyl 3-oxo-7 alpha-hydroxy-5 beta-cholane-24-carboxylate, provided a high yield of methyl 3 alpha, 7 alpha-dihydroxy-5 alpha-cholane-24-carboxylate. Treatment of this ester with an excess of methyl magnesium iodide afforded 5 alpha-cholestane-3 alpha, 7 alpha, 25-triol. The products were characterized by thin-layer and gas liquid chromatography, proton resonance, infrared and mass spectrometry.

  DOI：

  10.1016/0039-128x(81)90080-5