methyl 3α,7α-dihydroxy-5β-cholane-24-carboxylate | 38636-81-6

• 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 3α,7α-dihydroxy-5β-cholane-24-carboxylate
• 英文别名: 25-Homo-chenodesoxycholsaeuremethylester；methyl (5R)-5-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]hexanoate
• CAS: 38636-81-6
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: DQNZAUISCWIAHU-BJLOMENOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 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：
  0.96
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3α,7α-dihydroxy-5β-cholane-24-carboxylate 在 selenium(IV) oxide 、 silver carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 26.0h， 生成 7α,25-dihydroxy-4-cholesten-3-one
  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：

  鹅去氧胆酸 以 乙醚 为溶剂， 反应 2.0h， 生成 methyl 3α,7α-dihydroxy-5β-cholane-24-carboxylate
  参考文献：
  名称：

  Mehrwertige Alkohole aus Sterinen und Sterinderivaten，VI斯特雷德米特Strecturmerkmalen des Ecdysons und der Elatericine

  摘要：

  AUS Litho-，Desoxy- UNDChenodesoxycholsäure（1A - C ^）wurden黚死Homosäuren 5A - Ç模具叔-C 25 -Carbinole 7A - Ç dargestellt。位于Das Ecdyson-Analoge Produkt 18b umwandeln中的胆固醇。Hyodesoxy- UNDHomohyodesoxycholsäurewurden裸片Tetrole部33a，b übergeführt。Aus 34a – d沸腾的硬脂酸酯37a – d mit diosphenolischer Struktur gewonnen。

  DOI：

  10.1002/jlac.19727580109

文献信息

• New bile alcohols — synthesis of 5β-cholestane-3α, 7α, 25-triol and 5β-cholestane-3α, 7α, 25-24(14C)-triol1
  作者：Bertram I. Cohen、G.S. Tint、Taiju Kuramoto、Erwin H. Mosbach

  DOI：10.1016/0039-128x(75)90093-8

  日期：1975.3

  the diformoxy derivative (II) using formic acid. Reaction of II with thionyl chloride yielded the acid chloride which was treated with diazomethane (CH 2 N 2 or 14 CH 2 N 2 ) to produce 3ga, 7α-diformoxy-24-oxo-25-diazo-25-homocholane (III, A or B). 25-Homochenodeoxycholic acid (IV, A or B) was formed from III by means of the Wolff rearrangement of the Arndt-Eistert synthesis. The methyl ester of V (A

  摘要 5β-胆甾烷-3α, 7α, 25-三醇和5β-胆甾烷-3α, 7α, 25-24( 14 C)-三醇由3α, 7α-二羟基-5β-胆酸（鹅去氧胆酸）合成。鹅去氧胆酸使用甲酸转化为二甲氧基衍生物(II)。II 与亚硫酰氯反应生成酰氯，用重氮甲烷（CH 2 N 2 或 14 CH 2 N 2 ）处理生成 3ga, 7α-diformoxy-24-oxo-25-diazo-25-homocholane (III, A或 B)。25-高鹅脱氧胆酸（IV、A 或 B）是通过 Arndt-Eistert 合成的沃尔夫重排由 III 形成的。V(A或B)的甲酯在醚中用甲基碘化镁处理以提供所需的三醇VI(A和B)。三醇通过质谱和元素分析进行​​鉴定，并通过薄层色谱和气液色谱进行表征。3α、7α、
• Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids
  作者：S.V. Hiremath、William H. Elliott

  DOI：10.1016/0039-128x(81)90080-5

  日期：1981.10

  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.