1-acetyl-2-chlorotetrafluorocyclobutene | 125065-94-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1-acetyl-2-chlorotetrafluorocyclobutene
• 英文别名: 1-(2-chloro-3,3,4,4-tetrafluorocyclobuten-1-yl)ethanone
• CAS: 125065-94-3
• 化学式: C₆H₃ClF₄O
• 分子量: 202.536
• InChiKey: WLQZJEQAQVZTHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  乙醇 、 1-acetyl-2-chlorotetrafluorocyclobutene 在 氢氧化钾 作用下， 反应 0.5h， 以73%的产率得到1-acetyl-2-ethoxytetrafluorocyclobutene
  参考文献：
  名称：

  Reaction of 1-chloroperfluorocycloalkene derivatives with nucleophiles

  摘要：

  1-Acetyl-2-chloroperfluorocycloalkenes and 1-benzoyl-2-chloroperfluorocycloalkenes have been prepared by the coupling of 2-chloroperfluorocycloalkenyl copper reagent with acetyl chloride and benzoyl chloride, respectively. Similarly, 1-chloro-2-(p-nitrophenyl)perfluoro-cyclopentene and -cyclohexene were prepared by the reaction of 2-chloroperfluorocyclo-pentenyl and -hexenyl copper reagent with p-nitroiodobenzene.The compounds contain not only highly activated double bands but also charge-stabilizing groups in vinylic positions. The reaction of these compounds has been studied with various nucleophiles. They were very susceptible to nucleophilic attack at the chlorine-bonded carbon atom. Cyclobutene and cyclopentene derivatives underwent interesting nucleophilic displacement reactions of vinylic chlorine with alkoxide, amine and triethyl phosphite without allylic rearrangement under mild conditions. The stabilization effect to the generated carbanion intermediate by the acyl or p-nitrophenyl group undoubtedly dictates selectivity.However, additional factors must be considered in cyclohexene derivatives in which both 'inward' and 'outward' eliminations occur from methoxide ion attack on perfluoroacyclohexene derivatives. Also the order of activating power for a double bond has been found to be benzoyl > acetyl >> p-nitrophenyl and 1-chlorotetrafluorocyclobutene derivatives were more reactive than 1-chlorohexafluorocyclopentene derivatives towards the various nucleophiles.

  DOI：

  10.1016/0022-1139(93)02893-j
• 作为产物：
  描述：

  2-chlorotetrafluorocyclobut-1-enylzinc iodide 、 乙酰氯 在 copper(I) bromide 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 以87%的产率得到1-acetyl-2-chlorotetrafluorocyclobutene
  参考文献：
  名称：

  Jeong, Yeon-Tae; Jung, Ji-Hun; Shin, Seong-Kwon, Journal of the Chemical Society. Perkin transactions I, 1991, # 6, p. 1601 - 1606

  摘要：

  DOI：

文献信息

• Preparation and reactions of 2-chloroperfluorocyclobutenyl copper reagent
  作者：Seong-Kwon Shin、Sam-Kwon Choi

  DOI：10.1016/s0022-1139(00)82731-1

  日期：1989.6
• SEONG-KWON, SHIN;SAM-KWON, CHOI, J. FLUOR. CHEM., 43,(1989) N, C. 439-441
  作者：SEONG-KWON, SHIN、SAM-KWON, CHOI

  DOI：——

  日期：——
• Jeong, Yeon-Tae; Jung, Ji-Hun; Shin, Seong-Kwon, Journal of the Chemical Society. Perkin transactions I, 1991, # 6, p. 1601 - 1606
  作者：Jeong, Yeon-Tae、Jung, Ji-Hun、Shin, Seong-Kwon、Kim, Yong-Gyu、Jeong, In-Howa、Choi, Sam-Kwon

  DOI：——

  日期：——
• Reaction of 1-chloroperfluorocycloalkene derivatives with nucleophiles
  作者：Ji-Hun Jung、Yeon-Tae Jeong、Sam-Kwon Choi

  DOI：10.1016/0022-1139(93)02893-j

  日期：1994.1

  1-Acetyl-2-chloroperfluorocycloalkenes and 1-benzoyl-2-chloroperfluorocycloalkenes have been prepared by the coupling of 2-chloroperfluorocycloalkenyl copper reagent with acetyl chloride and benzoyl chloride, respectively. Similarly, 1-chloro-2-(p-nitrophenyl)perfluoro-cyclopentene and -cyclohexene were prepared by the reaction of 2-chloroperfluorocyclo-pentenyl and -hexenyl copper reagent with p-nitroiodobenzene.The compounds contain not only highly activated double bands but also charge-stabilizing groups in vinylic positions. The reaction of these compounds has been studied with various nucleophiles. They were very susceptible to nucleophilic attack at the chlorine-bonded carbon atom. Cyclobutene and cyclopentene derivatives underwent interesting nucleophilic displacement reactions of vinylic chlorine with alkoxide, amine and triethyl phosphite without allylic rearrangement under mild conditions. The stabilization effect to the generated carbanion intermediate by the acyl or p-nitrophenyl group undoubtedly dictates selectivity.However, additional factors must be considered in cyclohexene derivatives in which both 'inward' and 'outward' eliminations occur from methoxide ion attack on perfluoroacyclohexene derivatives. Also the order of activating power for a double bond has been found to be benzoyl > acetyl >> p-nitrophenyl and 1-chlorotetrafluorocyclobutene derivatives were more reactive than 1-chlorohexafluorocyclopentene derivatives towards the various nucleophiles.