3-oxo-12α-formoxy-4-cholen-24-oic acid | 88674-55-9

• 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: 3-oxo-12α-formoxy-4-cholen-24-oic acid
• 英文别名: (4R)-4-[(8R,9S,10R,12S,13R,14S,17R)-12-formyloxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 88674-55-9
• 化学式: C₂₅H₃₆O₅
• 分子量: 416.558
• InChiKey: LNRSBLMPYSPXBS-ZAJRCTALSA-N

物化性质

• 熔点：
  195-197 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  567.1±49.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-oxo-12α-formoxy-4-cholen-24-oic acid 在 sodium hydroxide 作用下， 以86%的产率得到12α-hydroxy-3-oxochol-4-en-24-oic acid
  参考文献：
  名称：

  Improved synthesis of 3-keto, 4-ene-3-keto, and 4,6-diene-3-keto bile acids

  摘要：

  Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80% yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups. The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60% yield, via bromination, dehydrobromination, and deformylation. By extending the dehydrobromination reaction, the 7 alpha-formoxyl group of the intermediate 4-ene-3-keto-7 alpha,12 alpha-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.

  DOI：

  10.1016/0039-128x(83)90087-9
• 作为产物：
  描述：

  4β-bromo-12α-formyloxy-3-oxo-5β-cholanoic acid 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到3-oxo-12α-formoxy-4-cholen-24-oic acid
  参考文献：
  名称：

  Improved synthesis of 3-keto, 4-ene-3-keto, and 4,6-diene-3-keto bile acids

  摘要：

  Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80% yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups. The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60% yield, via bromination, dehydrobromination, and deformylation. By extending the dehydrobromination reaction, the 7 alpha-formoxyl group of the intermediate 4-ene-3-keto-7 alpha,12 alpha-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.

  DOI：

  10.1016/0039-128x(83)90087-9

文献信息

• IIDA, TAKASHI;TAMARU, TAMAAKI;CHANG, FREDERIC C.;GOTO, JUNICHI;NAMBARA, T+, J. LIPID RES., 32,(1991) N, C. 649-658
  作者：IIDA, TAKASHI、TAMARU, TAMAAKI、CHANG, FREDERIC C.、GOTO, JUNICHI、NAMBARA, T+

  DOI：——

  日期：——