methyl 7,7-dichloro-6-oxoheptanoate | 87274-36-0

• 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: methyl 7,7-dichloro-6-oxoheptanoate
• CAS: 87274-36-0
• 化学式: C₈H₁₂Cl₂O₃
• 分子量: 227.087
• InChiKey: BWSXRESMCJLNGH-UHFFFAOYSA-N

物化性质

• 沸点：
  285.4±30.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  己二酸二甲酯 、 二氯甲烷 在 lithium dicyclohexylamide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.08h， 以52%的产率得到methyl 7,7-dichloro-6-oxoheptanoate
  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

• Photochemistry of α,α-disubstituted bicyclic cyclobutanones - a potential thermal-photochemical metathesis reaction
  作者：Edward Lee-Ruff、Alan C. Hopkinson、Hira Kazarians-Moghaddam

  DOI：10.1016/s0040-4039(00)81845-6

  日期：1983.1

  Under certain conditions the photolysis of α,α-disubstituted cyclobutanones give terminal olefinic esters. A two-stage thermal photochemical metathesis is described.

  在某些条件下，α，α-二取代的环丁酮的光解反应可生成末端烯烃酯。描述了两阶段热光化学复分解。
• LEE-RUFF, E.;HOPKINSON, A. C.;KAZARIANS-MOGHADDAM, H., TETRAHEDRON LETT., 1983, 24, N 20, 2067-2070
  作者：LEE-RUFF, E.、HOPKINSON, A. C.、KAZARIANS-MOGHADDAM, H.

  DOI：——

  日期：——
• 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.