1,1,3-trichloro-4-(perfluoro-1,1-dimethylbutyl)but-1-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,3-trichloro-4-(perfluoro-1,1-dimethylbutyl)but-1-ene
• 英文别名: 1,1,3-Trichloro-6,6,7,7,8,8,8-heptafluoro-5,5-bis(trifluoromethyl)oct-1-ene；1,1,3-trichloro-6,6,7,7,8,8,8-heptafluoro-5,5-bis(trifluoromethyl)oct-1-ene
• 化学式: C₁₀H₄Cl₃F₁₃
• 分子量: 477.48
• InChiKey: AUDZZSTUYFMNBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4-(perfluoro-1,1-dimethylbutyl)-1,1,1,3-tetrachlorobutane 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以7%的产率得到1,1,3-trichloro-4-(perfluoro-1,1-dimethylbutyl)but-1-ene
  参考文献：
  名称：

  Synthetic utility of 3-(perfluoro-1,1-dimethylbutyl)prop-1-ene. Part VI. A free-radical addition of CCl4 and CBr4 and dehydrohalogenation of the adducts

  摘要：

  Heating the title compound 1 in excess CCl4 and in the presence of a free-radical initiator (t-butyl peroxide) at 120 degrees C afforded 1,1,1,3-tetrachloro-4-(perfluoro-1,1-dimethylbutyl)butane (2) as the main product together with considerable amounts of cyclic dimer, 1,4-bis(perfluoro-1,1-dimethylbutyl)cyclohexane (3). Reaction of 1 with CBr4 at 120 degrees C gave 1,1,1,3-tetrabromo-4-(perfluoro-1,1-dimethylbutyl)butane (4) as the sole product while at 220 degrees C a mixture of 1,2-dibromo-3-(perfluoro-1,1-dimethylbutyl)propane (5) and 1,1-dibromo-4-(perfluoro-1,1-dimethylbutyl)buta-1,3-diene (6) was formed. Treatment of adducts 2 and 4 with methanolic potassium hydroxide at ambient temperature gave mixtures of 1,1,3-trihalo-4-(perfluoro-1,1-dimethylbutyl)but-1-enes (7) or (8) and 1,1-dihalo-4-(perfluoro-1,1-dimethylbutyl (9) or (6) in ratios depending on the adduct to base ratio and on the reaction conditions. Using an excess of the base and reflux temperature, adduct 4 and diene 6 were converted into methyl 4-(perfluoro-1,1-dimethylbutyl)buten-3-oate (10).

  DOI：

  10.1016/0022-1139(94)03125-j

文献信息

• Synthetic utility of 3-(perfluoro-1,1-dimethylbutyl)prop-1-ene. Part VI. A free-radical addition of CCl4 and CBr4 and dehydrohalogenation of the adducts
  作者：Halina Plenkiewicz、Wojciech Dmowski

  DOI：10.1016/0022-1139(94)03125-j

  日期：1995.2

  Heating the title compound 1 in excess CCl4 and in the presence of a free-radical initiator (t-butyl peroxide) at 120 degrees C afforded 1,1,1,3-tetrachloro-4-(perfluoro-1,1-dimethylbutyl)butane (2) as the main product together with considerable amounts of cyclic dimer, 1,4-bis(perfluoro-1,1-dimethylbutyl)cyclohexane (3). Reaction of 1 with CBr4 at 120 degrees C gave 1,1,1,3-tetrabromo-4-(perfluoro-1,1-dimethylbutyl)butane (4) as the sole product while at 220 degrees C a mixture of 1,2-dibromo-3-(perfluoro-1,1-dimethylbutyl)propane (5) and 1,1-dibromo-4-(perfluoro-1,1-dimethylbutyl)buta-1,3-diene (6) was formed. Treatment of adducts 2 and 4 with methanolic potassium hydroxide at ambient temperature gave mixtures of 1,1,3-trihalo-4-(perfluoro-1,1-dimethylbutyl)but-1-enes (7) or (8) and 1,1-dihalo-4-(perfluoro-1,1-dimethylbutyl (9) or (6) in ratios depending on the adduct to base ratio and on the reaction conditions. Using an excess of the base and reflux temperature, adduct 4 and diene 6 were converted into methyl 4-(perfluoro-1,1-dimethylbutyl)buten-3-oate (10).