Diethyl n-hexylmalonate-d

• 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: Diethyl n-hexylmalonate-d
• 英文别名: Diethyl 2-deuterio-2-hexylpropanedioate
• 化学式: C₁₃H₂₄O₄
• 分子量: 245.323
• InChiKey: HSHMTDVEKPAEGS-WORMITQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-二碘己烷 、 丙二酸二乙酯-D2 在 2,3,5-trimethylfuro<2,3-e>pyrano<2,3-b>pyridin-7-one 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-己烯 、 正己烷 、 1,5-已二烯 、 Diethyl n-hexylmalonate-d
  参考文献：
  名称：

  Electrochemical Reduction of 1,6-Dihalohexanes at Carbon Cathodes in Dimethylformamide

  摘要：

  Cyclic voltammograms for the reduction of 1,6-dibromo-, 1,6-diiodo-, 1-bromo-6-chloro-, and 1-chloro-6-iodohexane at glassy carbon electrodes in dimethylformamide containing tetramethylammonium perchlorate exhibit single irreversible waves that correspond to the reductive cleavage of carbon-bromine or carbon-iodine bonds. When large-scale controlled-potential electrolyses of either 1,6-dibromo- or 1,6-diiodohexane are performed at reticulated vitreous carbon, the principal products are n-hexane (30-45%), 1-hexene (28-34%), 1,5-hexadiene (6-16%), and cyclohexane (<7%), with n-dodecane being another significant species obtained from 1,6-diiodohexane. Because a carbon-chlorine bond is not directly reducible, 1-bromo-6-chloro- and 1-chloro-5-iodohexane give rise mainly to 1-chlorohexane (47-64%), 6-chloro-1-hexene (20-33%), and 1,12-dichlorododecane (2-25%). From these product distributions, and with the aid of experiments done in the presence of deuterium-labeled reagents, we conclude that the electrolytic reduction of 1,6-diiodo- and 1-chloro-6-iodohexane involves both radical and carbanion intermediates, whereas only carbanionic pathways are important for electrolyses of 1,6-dibromo- and 1-bromo-6-chlorohexane.

  DOI：

  10.1021/jo00108a034

文献信息

• Electrochemical Reduction of 1,6-Dihalohexanes at Carbon Cathodes in Dimethylformamide
  作者：Mohammad S. Mubarak、Dennis G. Peters

  DOI：10.1021/jo00108a034

  日期：1995.2

  Cyclic voltammograms for the reduction of 1,6-dibromo-, 1,6-diiodo-, 1-bromo-6-chloro-, and 1-chloro-6-iodohexane at glassy carbon electrodes in dimethylformamide containing tetramethylammonium perchlorate exhibit single irreversible waves that correspond to the reductive cleavage of carbon-bromine or carbon-iodine bonds. When large-scale controlled-potential electrolyses of either 1,6-dibromo- or 1,6-diiodohexane are performed at reticulated vitreous carbon, the principal products are n-hexane (30-45%), 1-hexene (28-34%), 1,5-hexadiene (6-16%), and cyclohexane (<7%), with n-dodecane being another significant species obtained from 1,6-diiodohexane. Because a carbon-chlorine bond is not directly reducible, 1-bromo-6-chloro- and 1-chloro-5-iodohexane give rise mainly to 1-chlorohexane (47-64%), 6-chloro-1-hexene (20-33%), and 1,12-dichlorododecane (2-25%). From these product distributions, and with the aid of experiments done in the presence of deuterium-labeled reagents, we conclude that the electrolytic reduction of 1,6-diiodo- and 1-chloro-6-iodohexane involves both radical and carbanion intermediates, whereas only carbanionic pathways are important for electrolyses of 1,6-dibromo- and 1-bromo-6-chlorohexane.