(Z)-4-cyclohexyl-3-ethylidene-4-methyl-1-oxetan-2-one | 145475-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (Z)-4-cyclohexyl-3-ethylidene-4-methyl-1-oxetan-2-one
• 英文别名: (3Z)-4-cyclohexyl-3-ethylidene-4-methyloxetan-2-one
• CAS: 145475-69-0
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: TUWBDJRBLQTNTI-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-4-cyclohexyl-3-ethylidene-4-methyl-1-oxetan-2-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (1-methyl-1,2-butadienyl)cyclohexane
  参考文献：
  名称：

  Synthesis of allenes via thermal cycloreversion of .alpha.-alkylidene-.beta.-lactones

  摘要：

  This paper describes the application of the solution-phase [2 + 2] cycloreversion of alpha-alkylidene-beta-lactones as a practical method for the generation of substituted allenes. Upon heating in dimethylformamide solution at 110-125-degrees-C, these unsaturated beta-lactone derivatives undergo decarboxylation to provide allenes in good to excellent yield. Alpha-alkylidene-beta-lactones are conveniently prepared via the phenylselenylation of beta-lactone enolates followed by oxidative elimination of the resulting alpha-phenylseleno derivatives. The beta-lactone starting materials are synthesized by the addition of thiol ester enolates to ketones and aldehydes according to our recently reported procedure.

  DOI：

  10.1021/jo00054a011
• 作为产物：
  描述：

  4-cyclohexyl-3-ethyl-4-methyl-1-oxetan-2-one 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Z)-4-cyclohexyl-3-ethylidene-4-methyl-1-oxetan-2-one
  参考文献：
  名称：

  Synthesis of allenes via thermal cycloreversion of .alpha.-alkylidene-.beta.-lactones

  摘要：

  This paper describes the application of the solution-phase [2 + 2] cycloreversion of alpha-alkylidene-beta-lactones as a practical method for the generation of substituted allenes. Upon heating in dimethylformamide solution at 110-125-degrees-C, these unsaturated beta-lactone derivatives undergo decarboxylation to provide allenes in good to excellent yield. Alpha-alkylidene-beta-lactones are conveniently prepared via the phenylselenylation of beta-lactone enolates followed by oxidative elimination of the resulting alpha-phenylseleno derivatives. The beta-lactone starting materials are synthesized by the addition of thiol ester enolates to ketones and aldehydes according to our recently reported procedure.

  DOI：

  10.1021/jo00054a011