5-(3-氧代环丁基)戊酸乙酯 | 1019842-26-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-(3-氧代环丁基)戊酸乙酯
• 英文名称: 5-(3-oxo-cyclobutyl)-pentanoic acid ethyl ester
• 英文别名: Ethyl 5-(3-oxocyclobutyl)pentanoate；ethyl 5-(3-oxocyclobutyl)pentanoate
• CAS: 1019842-26-2
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: IHJRHQKNFSPYRT-UHFFFAOYSA-N

物化性质

• 沸点：
  278.6±13.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  5-(3-氧代环丁基)戊酸乙酯 、 1-benzyloxyallene 在 正丁基锂 、 diethylzinc 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 生成 5-[3-(1-benzyloxy-propa-1,2-dienyl)-3-hydroxy-cyclobutyl]-pentanoic acid ethyl ester 、 5-[3-(1-benzyloxy-propa-1,2-dienyl)-3-hydroxy-cyclobutyl]-pentanoic acid ethyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Diastereo- and Enantioselective Wagner−Meerwein Shift: Control of Absolute Stereochemistry in the C−C Bond Migration Event

  摘要：

  Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a pi-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the pi-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an alpha-chiral O-tertiary center which has various synthetic applications.

  DOI：

  10.1021/ja7111299
• 作为产物：
  描述：

  在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以5.6 g的产率得到5-(3-氧代环丁基)戊酸乙酯
  参考文献：
  名称：

  Palladium-Catalyzed Diastereo- and Enantioselective Wagner−Meerwein Shift: Control of Absolute Stereochemistry in the C−C Bond Migration Event

  摘要：

  Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a pi-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the pi-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an alpha-chiral O-tertiary center which has various synthetic applications.

  DOI：

  10.1021/ja7111299

文献信息

• Palladium-Catalyzed Diastereo- and Enantioselective Wagner−Meerwein Shift: Control of Absolute Stereochemistry in the C−C Bond Migration Event
  作者：Barry M. Trost、Jia Xie

  DOI：10.1021/ja7111299

  日期：2008.5.1

  Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a pi-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the pi-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an alpha-chiral O-tertiary center which has various synthetic applications.