ethyl 1-[(Z)-4-chlorobut-2-enyl]-2-oxocycloheptane-1-carboxylate | 781662-49-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 1-[(Z)-4-chlorobut-2-enyl]-2-oxocycloheptane-1-carboxylate
• CAS: 781662-49-5
• 化学式: C₁₄H₂₁ClO₃
• 分子量: 272.772
• InChiKey: GHQBAVCDSATNHZ-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-[(Z)-4-chlorobut-2-enyl]-2-oxocycloheptane-1-carboxylate 在 盐酸 、 potassium hydride 、 叔丁醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.67h， 生成 (3S,5R)-3-Vinyl-2-oxa-spiro[4.6]undecane-1,6-dione
  参考文献：
  名称：

  Synthesis of Bicyclo[4.n.1]alkanones

  摘要：

  Cyclic P-keto ester monoanions react with 1,4-dihalobutenes to give C-alkylated products which subsequently undergo a stereoselective S(N)2' O-alkylation reaction to yield functionalized enol ethers. When the starting material was ethyl cyclopentanone carboxylate, the C-alkylated product, treated with a base, directly afforded the functionalized bicyclo[4.2.1]nonanone. The enol ethers were submitted to a flash vacuum thermolysis (FVT) reaction to readily afford functionalized bicyclo[4.n.1] alkanones (n = 3, 4). This reaction sequence was applied to the synthesis of a functionalized tricyclo[7.4.1.0(1,5)]tetradecanone, which represents an analogue to the tricyclic core of ingenol.

  DOI：

  10.1021/jo048923q
• 作为产物：
  描述：

  2-氧代环庚烷甲酸乙酯 、 顺式-1,4-二氯-2-丁烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到ethyl 1-[(Z)-4-chlorobut-2-enyl]-2-oxocycloheptane-1-carboxylate
  参考文献：
  名称：

  Synthesis of Bicyclo[4.n.1]alkanones

  摘要：

  Cyclic P-keto ester monoanions react with 1,4-dihalobutenes to give C-alkylated products which subsequently undergo a stereoselective S(N)2' O-alkylation reaction to yield functionalized enol ethers. When the starting material was ethyl cyclopentanone carboxylate, the C-alkylated product, treated with a base, directly afforded the functionalized bicyclo[4.2.1]nonanone. The enol ethers were submitted to a flash vacuum thermolysis (FVT) reaction to readily afford functionalized bicyclo[4.n.1] alkanones (n = 3, 4). This reaction sequence was applied to the synthesis of a functionalized tricyclo[7.4.1.0(1,5)]tetradecanone, which represents an analogue to the tricyclic core of ingenol.

  DOI：

  10.1021/jo048923q

文献信息

• Synthesis of Bicyclo[4.<i>n</i>.1]alkanones
  作者：Joaquin Montalt、Frédéric Linker、Frédéric Ratel、Michel Miesch

  DOI：10.1021/jo048923q

  日期：2004.10.1

  Cyclic P-keto ester monoanions react with 1,4-dihalobutenes to give C-alkylated products which subsequently undergo a stereoselective S(N)2' O-alkylation reaction to yield functionalized enol ethers. When the starting material was ethyl cyclopentanone carboxylate, the C-alkylated product, treated with a base, directly afforded the functionalized bicyclo[4.2.1]nonanone. The enol ethers were submitted to a flash vacuum thermolysis (FVT) reaction to readily afford functionalized bicyclo[4.n.1] alkanones (n = 3, 4). This reaction sequence was applied to the synthesis of a functionalized tricyclo[7.4.1.0(1,5)]tetradecanone, which represents an analogue to the tricyclic core of ingenol.