1-acetyl-2-chlorohexafluorocyclopentene | 123145-77-7

• 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-chlorohexafluorocyclopentene
• 英文别名: 1-(2-chloro-3,3,4,4,5,5-hexafluorocyclopenten-1-yl)ethanone
• CAS: 123145-77-7
• 化学式: C₇H₃ClF₆O
• 分子量: 252.544
• InChiKey: NYYMJPVCEAMDGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  73-74 °C(Press: 50 Torr)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1-acetyl-2-chlorohexafluorocyclopentene 、 亚磷酸三乙酯 以 乙二醇二甲醚 为溶剂， 反应 8.0h， 以78%的产率得到diethyl 2-acetylhexafluoro-1-cyclopentene-1-yl phosphonate
  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-chlorohexafluorocyclopent-1-enylcopper 、 乙酰氯 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到1-acetyl-2-chlorohexafluorocyclopentene
  参考文献：
  名称：

  2-氯六氟环戊烯基铜试剂的合成及化学反应性

  摘要：

  2-氯六氟环戊烯基铜试剂很容易在温和的条件下从1-氯-2-碘六氟环戊烯原位生产，可直接用于合成以前无法获得的取代多氟环戊烯。

  DOI：

  10.1039/c39880001478

文献信息

• Synthesis and chemical reactivity of 2-chlorohexafluorocyclopentenylcopper reagent
  作者：Sam-Kwon Choi、Yeon-Tae Jeong

  DOI：10.1039/c39880001478

  日期：——

  2-Chlorohexaflurocyclopentenylcopper reagent is readily produced in situ from 1-chloro-2-iodohexafluorocyclopentene under mild conditions and can be directly utilised in the synthesis of previously inaccessible substituted polyfluorocyclopentenes.

  2-氯六氟环戊烯基铜试剂很容易在温和的条件下从1-氯-2-碘六氟环戊烯原位生产，可直接用于合成以前无法获得的取代多氟环戊烯。
• CHOI, SAM-KWON;JEONG, YEON-TAE, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 22, C. 1478-1479
  作者：CHOI, SAM-KWON、JEONG, YEON-TAE

  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.