(3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸 | 64986-86-3

• 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
• 中文名称: (3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸
• 英文名称: 7,12 diformate of cholic acid
• 英文别名: 7,12-diformylcholic acid；3α-hydroxy-7α,12α-diformyloxy-5β-cholan-24-oic acid；3a-Hydroxy-7a,12a-diformyloxy-5b-cholan-24-oic acid；(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diformyloxy-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 64986-86-3
• 化学式: C₂₆H₄₀O₇
• 分子量: 464.599
• InChiKey: DAKGJCRYZHTYJF-HZAMXZRMSA-N

物化性质

• 熔点：
  96-99 °C
• 沸点：
  589.9±50.0 °C(Predicted)
• 密度：
  1.21

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以92%的产率得到3-oxo-7α,12α-diformoxy-5β-cholan-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：

  cholic acid triformate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (3alpha,5beta,7alpha,12alpha)-7,12-双(甲酰氧基)-3-羟基胆烷-24-酸
  参考文献：
  名称：

  The “triamino-analogue” of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry

  摘要：

  胆酸1已被转化为三胺5，具有全反式多环异胆酰基骨架和共同定向的轴向氨基基团；该体系的潜在支架作用通过转化为预组织的阴离子受体得到了展示。

  DOI：

  10.1039/b602415g

文献信息

• The “triamino-analogue” of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry
  作者：Khadga M. Bhattarai、Vicente del Amo、Germinal Magro、Adam L. Sisson、Jean-Baptiste Joos、Jonathan P. H. Charmant、Anob Kantacha、Anthony P. Davis

  DOI：10.1039/b602415g

  日期：——

  Cholic acid 1 has been converted into triamine 5 with the all-trans polycyclic allocholanoyl skeleton and co-directed, axial amino groups; the potential of this system as a scaffold is illustrated by conversion to a preorganised anion receptor.

  胆酸1已被转化为三胺5，具有全反式多环异胆酰基骨架和共同定向的轴向氨基基团；该体系的潜在支架作用通过转化为预组织的阴离子受体得到了展示。
• Synthesis of 3-glucuronides of unconjugated and conjugated bile acids.
  作者：JUNICHI GOTO、KAZUHIKO SUZAKI、TOSHIO NAMBARA

  DOI：10.1248/cpb.28.1258

  日期：——

  The 3-glucuronides of unconjugated, glyco- and tauro-conjugated bile acids have been prepared by an unequivocal route. Among three synthetic routes leading to the desired compounds, a method involving glucuronidation of the p-nitrophenyl ester by means of the Koenigs-Knorr reaction and subsequent conversion of the activated ester into the glyco-and tauro-conjugates was found to be most suitable. The nuclear magnetic resonance spectral data for bile acid glucuronides and related compounds are tabulated.

  非结合胆汁酸、糖结合胆汁酸和牛磺结合胆汁酸的 3-葡萄糖醛酸苷是通过一种明确的途径制备出来的。在获得所需化合物的三种合成路线中，通过柯尼希斯-克诺尔（Koenigs-Knorr）反应对硝基苯酯进行葡萄糖醛酸化，然后将活化的酯转化为糖型和牛磺酸型共轭物的方法最为合适。胆汁酸葡萄糖醛酸和相关化合物的核磁共振光谱数据已列表。
• Zhu, Xingpei; Amouzou, Etchri; McLean, Stewart, Canadian Journal of Chemistry, 1987, vol. 65, p. 2447 - 2449
  作者：Zhu, Xingpei、Amouzou, Etchri、McLean, Stewart

  DOI：——

  日期：——
• KRAMER, WERNER;SCHNEIDER, STEPHAN, J. LIPID RES., 30,(1989) N, C. 1281-1288
  作者：KRAMER, WERNER、SCHNEIDER, STEPHAN

  DOI：——

  日期：——
• ZHU, XINGPEI;AMOUZOU, ETCHRI;MCLEAN, STEWART, CAN. J. CHEM., 65,(1987) N 10, 2447-2449
  作者：ZHU, XINGPEI、AMOUZOU, ETCHRI、MCLEAN, STEWART

  DOI：——

  日期：——