ethyl 2,2-dichlorooctanoate

• 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 2,2-dichlorooctanoate
• 化学式: C₁₀H₁₈Cl₂O₂
• 分子量: 241.158
• InChiKey: PDAXSUHVGNNJLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-己烯 、 三氯乙酸乙酯 在 TiO₂#dotAg 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以3%的产率得到ethyl 2,2,4-trichlorooctanoate
  参考文献：
  名称：

  Addition Reaction of Polychloro Compounds to Carbon-Carbon Multiple Bonds Catalyzed by Semiconductor Particles under Photoirradiation

  摘要：

  Polychloro compounds were added to olefins in the presence of semiconductor particles (TiO2 or CdS) under photoirradiation. The photoreaction without semiconductors afforded no adducts at all; however, loading of TiO2 with Ag, Cu, or Fe3O4 enhanced the yield of the photoaddition reaction even further. Semiconductors operate as catalysts for the one-electron injection into the polychloro compounds. The relative adsorptions of the polychloro compounds onto the semiconductor particles correlate with the yields of the adducts, while the half-wave reduction potentials of the polychlorides do not. This semiconductor-catalyzed reaction was selective to unfunctionalized olefins and to those bearing a functional group at a remote position. An alkyne furnished the product via further reduction following addition, i.e., 1,1,3-trichloro-1-heptene (7) from 1-hexyne and carbon tetrachloride.

  DOI：

  10.1021/jo00085a013

文献信息

• Addition Reaction of Polychloro Compounds to Carbon-Carbon Multiple Bonds Catalyzed by Semiconductor Particles under Photoirradiation
  作者：Michiharu Mitani、Takuya Kiriyama、Tomoaki Kuratate

  DOI：10.1021/jo00085a013

  日期：1994.3

  Polychloro compounds were added to olefins in the presence of semiconductor particles (TiO2 or CdS) under photoirradiation. The photoreaction without semiconductors afforded no adducts at all; however, loading of TiO2 with Ag, Cu, or Fe3O4 enhanced the yield of the photoaddition reaction even further. Semiconductors operate as catalysts for the one-electron injection into the polychloro compounds. The relative adsorptions of the polychloro compounds onto the semiconductor particles correlate with the yields of the adducts, while the half-wave reduction potentials of the polychlorides do not. This semiconductor-catalyzed reaction was selective to unfunctionalized olefins and to those bearing a functional group at a remote position. An alkyne furnished the product via further reduction following addition, i.e., 1,1,3-trichloro-1-heptene (7) from 1-hexyne and carbon tetrachloride.