3α-hydroxy-7α-acetoxy-12-oxo-5β-cholanoic acid-(24) | 77499-22-0

• 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: 3α-hydroxy-7α-acetoxy-12-oxo-5β-cholanoic acid-(24)
• 英文别名: 3α-Hydroxy-7α-acetoxy-12-oxo-5β-cholansaeure-(24)；(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-acetyloxy-3-hydroxy-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 77499-22-0
• 化学式: C₂₆H₄₀O₆
• 分子量: 448.6
• InChiKey: XQVPUYVJDCWVQR-VYARKJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-7α-acetoxy-12-oxo-5β-cholanoic acid-(24) 在 无水碳酸镉 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 吡啶 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 12.0h， 生成 tauro-12-dehydrocholic acid 7-acetate 3-glucuronide acetate-methyl ester
  参考文献：
  名称：

  Studies on analysis of bile acids. Preparation of 3-glucuronides of 7- and 12-oxo bile acids.

  摘要：

  已合成具有7-或12-氧基团的未结合和糖结合、牛磺酸结合胆汁酸的3-葡萄糖醛酸酯。在C-3位引入葡萄糖醛酸残基是通过使用碳酸镉作为催化剂的Koenigs-Knorr反应实现的。结合胆汁酸的3-葡萄糖醛酸酯是通过三个串联反应制备的：与对硝基苯酚酯化、在C-3位进行葡萄糖醛酸化，以及与乙基甘氨酸或牛磺酸形成酰胺。简要讨论了氧基胆汁酸及相关化合物的3-葡萄糖醛酸酯的核磁共振光谱特性。

  DOI：

  10.1248/cpb.30.4422
• 作为产物：
  描述：

  3α,7α-diacetoxy-12-one-5β-cholan-24-oic acid 在 sodium hydroxide 作用下， 生成 3α-hydroxy-7α-acetoxy-12-oxo-5β-cholanoic acid-(24)
  参考文献：
  名称：

  Wieland; Kapitel, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1932, vol. 212, p. 269,273

  摘要：

  DOI：

文献信息

• Cyclocholates with 12-Oxo and 7,12-Oxo Groups
  作者：Hongwu Gao、Jerry Ray Dias

  DOI：10.1002/(sici)1099-0690(199804)1998:4<719::aid-ejoc719>3.0.co;2-f

  日期：1998.4

  Syntheses of bile acid cyclooligomers with 12- and 7,12-oxo groups (6a-d, 7a-c, 8a-b) by the Yamaguchi method are described. Cyclotrimerization is the principal reaction route for these cholic acid systems. Conversion of 7- and 12-hydroxy groups in cholic acid (1a-b) to oxo groups (4a-c, 5a-c), followed by macrocyclization (6a-d, 7a-c, 8a-b) and selective reduction of the oxo groups back to hydroxy ones without cleaving the 24-carboxylic ester Linkages (11) constitutes a new strategy in the synthesis of cyclocholates having unprotected hydroxy groups.
• Goto, Junichi; Kato, Hiroaki; Kaneko, Kiyoshi, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 11, p. 3389 - 3394
  作者：Goto, Junichi、Kato, Hiroaki、Kaneko, Kiyoshi、Nambara, Toshio

  DOI：——

  日期：——
• Studies on analysis of bile acids. Preparation of 3-glucuronides of 7- and 12-oxo bile acids.
  作者：JUNICHI GOTO、KAZUHIKO SUZAKI、TOSHIO NAMBARA

  DOI：10.1248/cpb.30.4422

  日期：——

  The 3-glucuronides of unconjugated and glyco- and tauro-conjugated bile acids having a 7- or 12-oxo group have been synthesized. Introduction of a glucuronyl residue at the C-3 position was achieved by the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. The 3-glucuronides of conjugated bile acids were prepared by three sequential reactions : esterification with p-nitrophenol, glucuronidation at C-3, and amide formation with ethyl glycinate or taurine. The nuclear magnetic resonance spectral properties of 3-glucuronides of oxo bile acids and related compounds are briefly discussed.

  已合成具有7-或12-氧基团的未结合和糖结合、牛磺酸结合胆汁酸的3-葡萄糖醛酸酯。在C-3位引入葡萄糖醛酸残基是通过使用碳酸镉作为催化剂的Koenigs-Knorr反应实现的。结合胆汁酸的3-葡萄糖醛酸酯是通过三个串联反应制备的：与对硝基苯酚酯化、在C-3位进行葡萄糖醛酸化，以及与乙基甘氨酸或牛磺酸形成酰胺。简要讨论了氧基胆汁酸及相关化合物的3-葡萄糖醛酸酯的核磁共振光谱特性。
• Wieland; Kapitel, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1932, vol. 212, p. 269,273
  作者：Wieland、Kapitel

  DOI：——

  日期：——