(3beta,5beta,7alpha,12alpha)-3-(甲酰氧基)-7,12-二羟基胆烷-24-酸甲酯 | 42921-40-4

• 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
• 中文名称: (3beta,5beta,7alpha,12alpha)-3-(甲酰氧基)-7,12-二羟基胆烷-24-酸甲酯
• 英文名称: methyl 3β-(formyloxy)-7α,12α-dihydroxy-5β-cholanate
• 英文别名: methyl (4R)-4-[(3S,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3-formyloxy-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]pentanoate
• CAS: 42921-40-4
• 化学式: C₂₆H₄₂O₆
• 分子量: 450.616
• InChiKey: FWYFJXRFKRLLLV-SZNCYGQESA-N

物化性质

• 沸点：
  546.7±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、四氢呋喃

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3beta,5beta,7alpha,12alpha)-3-(甲酰氧基)-7,12-二羟基胆烷-24-酸甲酯 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.13h， 生成 methyl 3β-methacryloyloxy-7α,12α-dihydroxy-5β-cholanoate
  参考文献：
  名称：

  Stereoselective synthesis of 3β-bile acid derivatives from the 3ga-analog

  摘要：

  The stereoselective transformation from the commonly occurring 3 alpha-bile acids and derivatives to their 3 beta-analogs is important for certain applications of these amphiphilic natural compounds, especially in the preparation of polymers. We report here the stereoselective conversion of methyl cholate to its 3 beta-hydroxy epimer by the use of the Mitsunobu reaction and to a 3 beta-amino cholic acid analog via a tosylation followed by a S(n)2 displacement with sodium azide and a hydrogenation of the azide group with overall yields of 86% and 78%, respectively. The preparation of the methacrylate and methacrylamide derivatives from these compounds is also described.

  DOI：

  10.1016/0009-3084(95)02476-y
• 作为产物：
  描述：

  甲酸 、 胆酸甲酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 (3beta,5beta,7alpha,12alpha)-3-(甲酰氧基)-7,12-二羟基胆烷-24-酸甲酯
  参考文献：
  名称：

  Stereoselective synthesis of 3β-bile acid derivatives from the 3ga-analog

  摘要：

  The stereoselective transformation from the commonly occurring 3 alpha-bile acids and derivatives to their 3 beta-analogs is important for certain applications of these amphiphilic natural compounds, especially in the preparation of polymers. We report here the stereoselective conversion of methyl cholate to its 3 beta-hydroxy epimer by the use of the Mitsunobu reaction and to a 3 beta-amino cholic acid analog via a tosylation followed by a S(n)2 displacement with sodium azide and a hydrogenation of the azide group with overall yields of 86% and 78%, respectively. The preparation of the methacrylate and methacrylamide derivatives from these compounds is also described.

  DOI：

  10.1016/0009-3084(95)02476-y

文献信息

• Potential bile acid metabolites. 7. 3,7,12-Trihydroxy-5.beta.-cholanic acids and related compounds
  作者：Takashi Iida、Frederic C. Chang

  DOI：10.1021/jo00136a031

  日期：1982.7