1-cyclohexyl-1-hydroxy-3-penten-2-one | 241484-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-1-hydroxy-3-penten-2-one
• 英文别名: (E)-1-cyclohexyl-1-hydroxypent-3-en-2-one
• CAS: 241484-66-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: BSYXEYIEUYIZJY-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己烷基甲醛 在 正丁基锂 、 silver nitrate 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-cyclohexyl-1-hydroxy-3-penten-2-one
  参考文献：
  名称：

  Nucleophilic alkenoylation of aldehydes with metalated α-aminonitriles: regioselective synthesis of α-hydroxyenones

  摘要：

  An efficient regioselective two-step synthesis of alpha-hydroxyenones 3a-p is reported. The methodology involves nucleophilic addition of metalated beta,gamma-unsaturated-alpha-aminonitriles to aldehydes, followed by a mild silver nitrate induced hydrolysis of the aminonitrile adducts to afford the title compounds in overall yields of 61-83%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00953-3

文献信息

• Three-carbon annelations. Regiocontrolled reactivity of trimethylsilyl- and ethoxyethyl-protected cyanohydrins. Versatile homoenolate and acyl anion equivalents
  作者：Richard M. Jacobson、George P. Lahm、John W. Clader

  DOI：10.1021/jo01291a005

  日期：1980.2
• Nucleophilic alkenoylation of aldehydes with metalated α-aminonitriles: regioselective synthesis of α-hydroxyenones
  作者：Fabrice Pierre、Dieter Enders

  DOI：10.1016/s0040-4039(99)00953-3

  日期：1999.7

  An efficient regioselective two-step synthesis of alpha-hydroxyenones 3a-p is reported. The methodology involves nucleophilic addition of metalated beta,gamma-unsaturated-alpha-aminonitriles to aldehydes, followed by a mild silver nitrate induced hydrolysis of the aminonitrile adducts to afford the title compounds in overall yields of 61-83%. (C) 1999 Elsevier Science Ltd. All rights reserved.