7-Oxo-3β-hydroxycholestane-5α-carbonitrile | 2740-45-6

• 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: 7-Oxo-3β-hydroxycholestane-5α-carbonitrile
• 英文别名: 3β-Hydroxy-7-oxo-5α-cholestan-5-carbonitril；(3S,5S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-7-oxo-2,3,4,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-5-carbonitrile
• CAS: 2740-45-6
• 化学式: C₂₈H₄₅NO₂
• 分子量: 427.671
• InChiKey: DCIFXNAGBCWOEO-NOGRQRSOSA-N

物化性质

• 熔点：
  162-166 °C
• 沸点：
  550.9±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Oxo-3β-hydroxycholestane-5α-carbonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以92%的产率得到3β,7β-Dihydroxycholestane-5α,7α-carbolactam
  参考文献：
  名称：

  Syntheses of Substituted Succinimides by Radical .beta.-Fragmentation of Bicyclic Carbinol Amides. A New Expeditious Synthesis of 2-[2-(Methoxycarbonyl)ethyl]-3-[(methoxycarbonyl)methyl]- 3-methylsuccinimide, the Ring-B Imide of Vitamin B12

  摘要：

  A mild and efficient synthesis of substituted succinimides by radical beta-fragmentation of carbinol amides is described. The carbinol amides studied were generated by treatment of the corresponding alpha,beta-unsaturated ketones with hydrogen cyanide and subsequent hydrolysis of the cyanide intermediates. Photolysis with visible light in the presence of (diacetoxyiodo)benzene (DIB) and iodine of azabicyclic carbinol amides of the types 1-hydroxy-2-azabicyclo[3.3.0] octan-3-one (e.g., 4, 6, and 7) and 1-hydroxy-2-azabicyclo[3.2.1]octan-3-one (e.g., 16, 17, and 21) led to the substituted succinimides in good yields. A novel and operationally simple synthesis of the ring-B imide 28 is described, employing this P-fragmentation reaction on the carbinol amide 7 as the key step. The transformation of the resulting succinimide 11 into the target 28 was accomplished in one step by oxidation of the primary iodide and the phenyl group with RUO(4).

  DOI：

  10.1021/jo00089a021
• 作为产物：
  描述：

  5-胆甾烯-3β-醇-7-酮 、 氰化钾 在 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-Oxo-3β-hydroxycholestane-5α-carbonitrile
  参考文献：
  名称：

  Hydrocyanation. VI. Application of the new hydrocyanation methods to conjugate hydrocyanation of .alpha.,.beta.-unsaturated ketones, conjugated dienones, and conjugated enamines and to preparation of .alpha.-cyanohydrins

  摘要：

  DOI：

  10.1021/ja00768a039

文献信息

• Hydrocyanation. VI. Application of the new hydrocyanation methods to conjugate hydrocyanation of .alpha.,.beta.-unsaturated ketones, conjugated dienones, and conjugated enamines and to preparation of .alpha.-cyanohydrins
  作者：W. Nagata、M. Yoshioka、M. Murakami

  DOI：10.1021/ja00768a039

  日期：1972.6
• Syntheses of Substituted Succinimides by Radical .beta.-Fragmentation of Bicyclic Carbinol Amides. A New Expeditious Synthesis of 2-[2-(Methoxycarbonyl)ethyl]-3-[(methoxycarbonyl)methyl]- 3-methylsuccinimide, the Ring-B Imide of Vitamin B12
  作者：Rosendo Hernandez、Ernesto Suarez、Daniel Melian

  DOI：10.1021/jo00089a021

  日期：1994.5

  A mild and efficient synthesis of substituted succinimides by radical beta-fragmentation of carbinol amides is described. The carbinol amides studied were generated by treatment of the corresponding alpha,beta-unsaturated ketones with hydrogen cyanide and subsequent hydrolysis of the cyanide intermediates. Photolysis with visible light in the presence of (diacetoxyiodo)benzene (DIB) and iodine of azabicyclic carbinol amides of the types 1-hydroxy-2-azabicyclo[3.3.0] octan-3-one (e.g., 4, 6, and 7) and 1-hydroxy-2-azabicyclo[3.2.1]octan-3-one (e.g., 16, 17, and 21) led to the substituted succinimides in good yields. A novel and operationally simple synthesis of the ring-B imide 28 is described, employing this P-fragmentation reaction on the carbinol amide 7 as the key step. The transformation of the resulting succinimide 11 into the target 28 was accomplished in one step by oxidation of the primary iodide and the phenyl group with RUO(4).