3β,7β-Dihydroxycholestane-5α,7α-carbolactam | 158657-74-0

• 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: 3β,7β-Dihydroxycholestane-5α,7α-carbolactam
• 英文别名: (1S,3S,6R,7S,10R,11R,14S,15S,16S)-3,16-dihydroxy-6,10-dimethyl-11-[(2R)-6-methylheptan-2-yl]-17-azapentacyclo[14.2.1.01,6.07,15.010,14]nonadecan-18-one
• CAS: 158657-74-0
• 化学式: C₂₈H₄₇NO₃
• 分子量: 445.686
• InChiKey: DIINGXDRAPVPTL-VINRAIAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,7β-Dihydroxycholestane-5α,7α-carbolactam 在 吡啶 、 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成
  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：

  7-氧代胆甾-5-烯-3-beta-基乙酸酯 在 sodium hydroxide 、 氯化二乙基铝 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 9.0h， 生成 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

文献信息

• 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).