1-氯环丁烯 | 1473-54-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 1-氯环丁烯
• 英文名称: 1-chlorocyclobutene
• 英文别名: chlorocyclobutene；ethylenevinyl chloride；1-Chlor-cyclobuten-(1)；1-Chlor-cyclobuten；1-Chlorcyclobuten
• CAS: 1473-54-7
• 化学式: C₄H₅Cl
• 分子量: 88.5367
• InChiKey: KFDYVJZZXORXMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-氯环丁烯 在 溴 作用下， 以 氯仿 为溶剂， 生成 1-Chlor-1,2-dibrom-cyclobutan
  参考文献：
  名称：

  Wittig,G.; Wilson,E.R., Chemische Berichte, 1965, vol. 98, p. 451 - 457

  摘要：

  DOI：
• 作为产物：
  描述：

  cyclopropylchlorocarbene 在 吡啶 作用下， 以 异辛烷 为溶剂， 生成 1-氯环丁烯
  参考文献：
  名称：

  烷基氯卡宾中 1,2- 迁移率

  摘要：

  Les (烷基氯) 亚甲基子类光解 eclair des (烷基-3 氯-3) diazirines

  DOI：

  10.1021/ja00197a086

文献信息

• Comparison of syn dehydrohalogenations from -1-bromo-2-chlorocycloalkanes promoted by complex base and by potassium -butoxide
  作者：Alan P. Croft、Richard A. Bartsch

  DOI：10.1016/s0040-4039(00)88009-0

  日期：1983.1

  Compared with t-BuOK-t-BuOH, syn eliminations from trans-1-bromo-2-chlorocycloalkanes (C4-C8) induced by NaNH2-NaO-t-Bu in THF are rapid, exhibit greater propensity for dehydrechlorination and show little sensitivity to ring size of the dihalocycloalkane.

  与t-BuOK-t-BuOH相比，NaNH 2 -NaO-t-Bu在THF中诱导的反式1-溴-2-氯环烷烃（C 4 -C 8）的同构消除速度快，表现出更大的脱水氯化倾向，并且对二卤代环烷的环尺寸几乎不敏感。
• Kinetics of alkylhalocarbene rearrangements: modulation by fluorine substituents
  作者：Robert A. Moss、Guo Jie Ho、Weiguo Liu

  DOI：10.1021/ja00029a025

  日期：1992.1

  Rate constants were measured by laser flash photolytic methods for hydrogen and carbon 1,2-migrations in four different alkylchlorocarbenes and in the analogous alkylfluorocarbenes. The carbenes, products, and rate constants (s-1) were as follows: phenoxymethylchlorocarbene to (Z)- and (E)-1-chloro-2-phenoxyethene (Z/E approximately 4/1), k = 3.6 x 10(7); phenoxymethylfluorocarbene to (Z)-1-fluoro-2-phenoxyethene (Z/E > 10/1), k = 1.3 x 10(7); neopentylchlorocarbene to (Z)- and (E)-1-tert-butyl-2-chloroethene (Z/E = 1/12), k = 1.4 x 10(7); neopentylfluorocarbene to (Z)- and (E)-1-tert-butyl-2-fluoroethene (Z/E = 1/2.5), k = 2.6 X 10(6); cyclobutylchlorocarbene to 1-chlorocyclopentene (C migration) and chloromethylenecyclobutane (H migration), k(c) = 4.6 X 10(7), k(H) = 2.1 X 10(7); cyclobutylfluorocarbene to 1-fluorocyclopentene (C migration) and fluoromethylenecyclobutane (H migration), k(c) = 1.8 x 10(6), k(H) = 5.3 x 10(5); cyclopropylchlorocarbene to 1-chlorocyclobutene, k = 9 x 10(5); cyclopropylfluorocarbene to 1-fluorocyclobutene, k = 1.4 x 10(5). Activation energies for several of these processes were in the range of 2-4 kcal/mol, with A approximately 10(8)-10(9) s-1.
• Activation parameters for a 1,2 carbon shift in a carbene rearrangement
  作者：Robert A. Moss、Guo Jie Ho、Shilan Shen、Karsten Krogh-Jespersen

  DOI：10.1021/ja00160a059

  日期：1990.2
• A new synthesis of 3-fluoro- and 3-chlorocyclobutenes from dihalocyclobutanes. The five isomers of chlorofluorocyclobutane
  作者：Norman C. Craig、Steven S. Borick、Michael A. Fisher、Thomas R. Tucker、Yong-Zhuang Xiao

  DOI：10.1016/s0022-1139(00)82413-6

  日期：1992.11

  3-Fluorocyclobutene (1) and 3-chlorocyclobutene (2) have been obtained by simpler syntheses and in higher yield than previously reported. One of the synthetic steps involves a three-phase-transfer-catalysis technique that could be of wider utility. New examples are cited of applying AgF2, an underutilized reagent, as a fluorinating agent near room temperature. Compounds 1 and 2 have been characterized by mass, NMR and vibrational spectroscopies. The NMR spectra have been fully analyzed. Useful group frequencies in the vibrational spectra of halocyclobutenes have been identified. The five monochloro-monofluorocyclobutane precursors of fluorocyclobutenes have also been separated and characterized. From NMR coupling constants, conformer mixtures have been identified for three of the isomers.
• Elusive carbenes. Olefinic capture of cyclopropylchlorocarbene and related species
  作者：Robert A. Moss、Mary E. Fantina

  DOI：10.1021/ja00489a058

  日期：1978.10