ethyl (E)-5,5-dichloro-4-oxopent-2-enoate | 137777-26-5

• 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 (E)-5,5-dichloro-4-oxopent-2-enoate
• CAS: 137777-26-5
• 化学式: C₇H₈Cl₂O₃
• 分子量: 211.045
• InChiKey: IDSSVXQUJFNKPM-ONEGZZNKSA-N

物化性质

• 沸点：
  253.1±40.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  二氯甲烷 、 富马酸二乙酯 在 lithium dicyclohexylamide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.08h， 以60%的产率得到ethyl (E)-5,5-dichloro-4-oxopent-2-enoate
  参考文献：
  名称：

  Reactivity of in situ generated dihalomethyllithium towards dicarboxylic acid diesters and lactones: Synthetic applications

  摘要：

  The reaction of dicarboxylic acid diesters 1, with in situ generated dihalomethyllithium (1:1.4 molar ratio) at -78-degrees-C leads, after hydrolysis, to the corresponding dihalomethylketoesters 3. The same process using an excess of the carbenoid (1:4 molar ratio) yields the expected tetrahalodiketones 5. The reaction of these carbenoids with gamma- and delta-lactones 6 at -78-degrees-C yields, after hydrolysis, 2-(dihalomethyl) gamma- or delta-lactols 7 or 8, respectively. The reaction of lactols 7 or 8 with triethylsilane or allyltrimethylsilane in the presence of BF3.OEt2 affords the corresponding substituted tetrahydrofurans or pyrans 10 or 12. The use of epsilon-caprolactone as starting material in the reaction with dihalomethyllithium leads to the corresponding 1,1-dihalo-7-hydroxy-2-heptanones.

  DOI：

  10.1016/s0040-4020(01)81943-8

文献信息

• Reactivity of in situ generated dihalomethyllithium towards dicarboxylic acid diesters and lactones: Synthetic applications
  作者：José Barluenga、Luján Llavona、Miguel Yus、José M Concellón

  DOI：10.1016/s0040-4020(01)81943-8

  日期：1991.9

  The reaction of dicarboxylic acid diesters 1, with in situ generated dihalomethyllithium (1:1.4 molar ratio) at -78-degrees-C leads, after hydrolysis, to the corresponding dihalomethylketoesters 3. The same process using an excess of the carbenoid (1:4 molar ratio) yields the expected tetrahalodiketones 5. The reaction of these carbenoids with gamma- and delta-lactones 6 at -78-degrees-C yields, after hydrolysis, 2-(dihalomethyl) gamma- or delta-lactols 7 or 8, respectively. The reaction of lactols 7 or 8 with triethylsilane or allyltrimethylsilane in the presence of BF3.OEt2 affords the corresponding substituted tetrahydrofurans or pyrans 10 or 12. The use of epsilon-caprolactone as starting material in the reaction with dihalomethyllithium leads to the corresponding 1,1-dihalo-7-hydroxy-2-heptanones.