4-(ethoxycarbonyl)-2-ethylcyclohepta-2,4,6-trien-1-one | 136175-80-9

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 4-(ethoxycarbonyl)-2-ethylcyclohepta-2,4,6-trien-1-one
• 英文别名: Ethyl 6-ethyl-5-oxocyclohepta-1,3,6-triene-1-carboxylate
• CAS: 136175-80-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: GTMWPAQNDNGXDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-Diazo-hexa-3,5-dienoic acid ethyl ester 在 rhodium(II) pivalate 盐酸 、 柠檬酸 作用下， 以 四氢呋喃 、 水 、 正戊烷 为溶剂， 反应 1.33h， 生成 4-(ethoxycarbonyl)-2-ethylcyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Versatile synthesis of tropones by reaction of rhodium(II)-stabilized vinylcarbenoids with 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene

  摘要：

  Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene leads to [3 + 4] annulation products by a tandem cyclopropanation/Cope rearrangement sequence. The resulting cycloheptadienes are readily converted to cycloheptatrienones either by hydrolysis with mild acid followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or by treatment with dichloroethoxyoxovanadium. The efficiency of the general strategy was demonstrated through a short synthesis of nezukone.

  DOI：

  10.1021/jo00022a041

文献信息

• Versatile synthesis of tropones by reaction of rhodium(II)-stabilized vinylcarbenoids with 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene
  作者：Huw M. L. Davies、T. Jeffrey Clark、Garland F. Kimmer

  DOI：10.1021/jo00022a041

  日期：1991.10

  Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene leads to [3 + 4] annulation products by a tandem cyclopropanation/Cope rearrangement sequence. The resulting cycloheptadienes are readily converted to cycloheptatrienones either by hydrolysis with mild acid followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or by treatment with dichloroethoxyoxovanadium. The efficiency of the general strategy was demonstrated through a short synthesis of nezukone.