4-Carbethoxy-3-methylidene-6,8,8-trimethyl-(E)-cyclonon-5-en-1-one | 150352-12-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Carbethoxy-3-methylidene-6,8,8-trimethyl-(E)-cyclonon-5-en-1-one
• 英文别名: ethyl (2E)-3,5,5-trimethyl-9-methylidene-7-oxocyclonon-2-ene-1-carboxylate
• CAS: 150352-12-8
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: RSERQOFVCKJJBF-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-Carbethoxy-3-methylidene-6,8,8-trimethyl-(E)-cyclonon-5-en-1-one 在 aluminum oxide 作用下， 以 正己烷 、 乙酸乙酯 为溶剂， 以100%的产率得到4-Carbethoxy-1-hydroxy-3-methylidene-6,8,8-trimethylbicyclo<4.3.0>non-4-ene
  参考文献：
  名称：

  Studies in base-catalyzed allenic oxy-Cope rearrangement: an expedient synthesis of functionalized bicyclo[4.3.0] and -[4.4.0] systems and 3,5-cycloundecadien-1-one

  摘要：

  The base-catalyzed oxy-Cope rearrangement of systems incorporating an allenic pi system was studied. The rearrangement incidentally leads to functionalized bicyclo[4.3.0]nonane 15, bicyclo[4.4.0]decanes 6 and 10, and 3,5-cycloundecadien-1-one 20. The effect of ring size and nature of the base on the rearrangement was also studied.

  DOI：

  10.1021/jo00072a035
• 作为产物：
  描述：

  1-Allenyl-2-(2'-carbethoxyvinyl)-2,4,4-trimethylcyclopentan-1-ol 在 sodium ethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以90%的产率得到4-Carbethoxy-3-methylidene-6,8,8-trimethyl-(E)-cyclonon-5-en-1-one
  参考文献：
  名称：

  Studies in base-catalyzed allenic oxy-Cope rearrangement: an expedient synthesis of functionalized bicyclo[4.3.0] and -[4.4.0] systems and 3,5-cycloundecadien-1-one

  摘要：

  The base-catalyzed oxy-Cope rearrangement of systems incorporating an allenic pi system was studied. The rearrangement incidentally leads to functionalized bicyclo[4.3.0]nonane 15, bicyclo[4.4.0]decanes 6 and 10, and 3,5-cycloundecadien-1-one 20. The effect of ring size and nature of the base on the rearrangement was also studied.

  DOI：

  10.1021/jo00072a035