(12α)-12,24-bis(benzoyloxy)-4-oxachol-5-en-3-one | 473462-16-7

• 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: (12α)-12,24-bis(benzoyloxy)-4-oxachol-5-en-3-one
• 英文别名: [(4R)-4-[(1R,3aS,3bS,9aR,9bS,11S,11aR)-11-benzoyloxy-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,8,9,9b,10,11-decahydro-1H-indeno[5,4-f]chromen-1-yl]pentyl] benzoate
• CAS: 473462-16-7
• 化学式: C₃₇H₄₄O₆
• 分子量: 584.753
• InChiKey: FBMPPZVRDRDTOM-UENPKWHLSA-N

物化性质

• 沸点：
  686.1±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酰氯-13C2 、 (12α)-12,24-bis(benzoyloxy)-4-oxachol-5-en-3-one 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.12h， 生成 [(4R)-4-[(1R,3aS,3bS,9aR,9bS,11S,11aR)-8-acetyl-11-benzoyloxy-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,8,9,9b,10,11-decahydro-1H-indeno[5,4-f]chromen-1-yl]pentyl] benzoate
  参考文献：
  名称：

  Synthesis of [3,4-¹³C₂]-Enriched Bile Salts as NMR Probes of Protein−Ligand Interactions

  摘要：

  Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-C-13(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-C-13(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-C-13(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)- double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-C-13(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and H-1-C-13 HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.

  DOI：

  10.1021/jo0259109
• 作为产物：
  描述：

  去氧胆酸 在 吡啶 、 sodium tetrahydroborate 、 高氯酸 、 jones reagent 、 溴 、 sodium 、 乙酸酐 、 lithium carbonate 、 臭氧 、 溶剂黄146 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 15.59h， 生成 (12α)-12,24-bis(benzoyloxy)-4-oxachol-5-en-3-one
  参考文献：
  名称：

  Synthesis of [3,4-¹³C₂]-Enriched Bile Salts as NMR Probes of Protein−Ligand Interactions

  摘要：

  Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-C-13(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-C-13(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-C-13(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)- double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-C-13(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and H-1-C-13 HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.

  DOI：

  10.1021/jo0259109

文献信息

• Synthesis of [3,4-¹³C₂]-Enriched Bile Salts as NMR Probes of Protein−Ligand Interactions
  作者：Gregory P. Tochtrop、Gregory T. DeKoster、David P. Cistola、Douglas F. Covey

  DOI：10.1021/jo0259109

  日期：2002.9.1

  Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-C-13(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-C-13(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-C-13(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)- double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-C-13(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and H-1-C-13 HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.