2-氯环丁烯 | 93280-82-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 2-氯环丁烯
• 英文名称: 2-chlorocyclobutene
• 英文别名: 3-chlorocyclobutene；3-Chlorcyclobut-1-en
• CAS: 93280-82-1
• 化学式: C₄H₅Cl
• 分子量: 88.5367
• InChiKey: NGDXTAVUVLANKC-UHFFFAOYSA-N

物化性质

• 沸点：
  91.2±9.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：

  2-氯环丁烯 生成 1-氯丁-1,3-二烯
  参考文献：
  名称：

  Stereoselective substituent effects on conrotatory electrocyclic reactions of cyclobutenes

  摘要：

  DOI：

  10.1021/ja00337a067
• 作为产物：
  描述：

  cis-3,4-dichlorocyclobutene 在 三正丁基氢锡 作用下， 以65%的产率得到2-氯环丁烯
  参考文献：
  名称：

  Stereoselective substituent effects on conrotatory electrocyclic reactions of cyclobutenes

  摘要：

  DOI：

  10.1021/ja00337a067

文献信息

• Cycloalkane and Cycloalkene C−H Bond Dissociation Energies
  作者：Zhixin Tian、Alireza Fattahi、Lev Lis、Steven R. Kass

  DOI：10.1021/ja065348u

  日期：2006.12.1

  Both C-H bond dissociation energies for cyclobutene were measured in the gas phase (BDE = 91.2 +/- 2.3 (allyl) and 112.5 +/- 2.5 (vinyl) kcal mol-1) via a thermodynamic cycle by carrying out proton affinity and electron-binding energy measurements on 1- and 3-cyclobutenyl anions. The results were compared to those for an acyclic model compound, cis-2-butene, and provide the needed information to experimentally

  环丁烯的两个 CH 键解离能均在气相（BDE = 91.2 +/- 2.3（烯丙基）和 112.5 +/- 2.5（乙烯基）kcal mol-1）中通过热力学循环通过进行质子亲合力和电子- 1- 和 3- 环丁烯基阴离子的结合能测量。将结果与无环模型化合物顺式 2-丁烯的结果进行比较，并提供所需信息以通过实验确定环丁二烯的形成热。还对环烷烃、环烯烃和选定的参考化合物进行了化学准确的 G3 和 W1 计算。似乎通常引用的环丙烷、环丁烷和环己烷的键能 3 到 4 kcal mol-1 太小了，它们的 pi 键强度（如 BDE1 - BDE2 给出的）误差高达 8 kcal mol-1。
• 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.
• Vibrational spectra and assignments for 1-fluoro- and 1-chlorocyclobutenes: revised assignment for cyclobutene
  作者：Norman C. Craig、Steven S. Borick、Thomas R. Tucker、Yong Zhuang Xiao

  DOI：10.1021/j100162a023

  日期：1991.5

  Gas-phase infrared spectra and liquid-phase Raman spectra are presented for 1-chlorocyclobutene and 1-fluorocyclobutene. Complete assignments of vibrational fundamentals are proposed for these molecules of C(s) symmetry. For 1-chlorocyclobutene (cm-1): (a') 3090, 2947, 2940, 1595, 1452, 1434, 1250, 1197, 1165, 1120, 916, 891, 869, 493, 299; (a") 2980, 2966, 1140, 1070, 1016, 854, 751, 395, 211. For 1-fluorocyclobutene (cm-1): (a') 3111, 2954, 2948, 1667, 1464, 1437, 1306, 1214, 1189, 1154, 972, 911, 866, 651, 412; (a") 2982, 2969, 1142, 1076, 1020, 855, 764, 436, 264. Frequencies of CH-rich modes correlate closely for these isotopomer-like molecules. These results along with a Raman spectrum of liquid cyclobutene near -100-degrees-C have provided evidence for assigning five unsettled vibrational fundamentals of cyclobutene. These modes in cm-1 are (a2) nu-9 = 2944, nu-11 = 1011, and nu-12 = 846 and (b1) nu-19 = 903 and nu-20 = 888. Ring-puckering frequencies for a variety of halogen-substituted cyclobutenes are compared and found to follow an understandable pattern.
• KIRMSE, W.;RONDAN, N. G.;HOUK, K. N., J. AMER. CHEM. SOC., 1984, 106, N 25, 7989-7991
  作者：KIRMSE, W.、RONDAN, N. G.、HOUK, K. N.

  DOI：——

  日期：——
• The Heat of Formation of Cyclobutadiene
  作者：Alireza Fattahi、Lev Lis、Zhixin Tian、Steven R. Kass

  DOI：10.1002/anie.200600839

  日期：2006.7.24