(E,Z)-1,4-二氯-1,3-丁二烯 | 3588-13-4

• 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: (E,Z)-1,4-二氯-1,3-丁二烯
• 英文名称: cis,trans-1,4-dichloro-1,3-butadiene
• 英文别名: (Z,E)-1,4-dichloro-1,3-butadiene；(Z-E)-1,4-dichlorobutadiene；1c,4t-dichloro-buta-1,3-diene；cis.trans-1.4-Dichlor-butadien-(1.3)；cis,trans-1,4-Dichlor-1,3-butadien；trans,cis-1,4-Dichlor-1,3-butadien；(1E,3Z)-1,4-Dichlorobuta-1,3-diene；(1Z,3E)-1,4-dichlorobuta-1,3-diene
• CAS: 3588-13-4
• 化学式: C₄H₄Cl₂
• 分子量: 122.982
• InChiKey: LDZSRRMBFGBOAE-HSFFGMMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903299090

反应信息

• 作为反应物：
  描述：

  (E,Z)-1,4-二氯-1,3-丁二烯 生成 (E,Z)-<1,4-D2>-1,3-Butadien
  参考文献：
  名称：

  MUELLER, P.;JOLY, D.;MERMOUD, F., HELV. CHIM. ACTA, 1984, 67, N 1, 105-112

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-3,4-dichlorocyclobutene 以 various solvent(s) 为溶剂， 反应 36.0h， 以67%的产率得到(E,Z)-1,4-二氯-1,3-丁二烯
  参考文献：
  名称：

  2,3-二氯-5,6-二氰基对苯醌对1,4，-环己二烯脱氢的立体化学

  摘要：

  由顺-3，4-二氯环丁烯（5）合成了顺-和反-（3，6-D 2）-1，4-环己二烯1a和1b。用DDQ芳香化为苯是顺式立体特异性的，不确定度为5％。讨论了有关用2,3-二氯-5,6-二氰基对苯醌（DDQ）进行1,4-二氢芳烃芳构化的协同或逐步机理的结果。

  DOI：

  10.1002/hlca.19840670113

文献信息

• Production of orbitally forbidden products in the IR-laser-induced isomerization of cis-3,4-dichlorocyclobutene
  作者：Chung-Rei Mao、Nathan Presser、Lian-Shun John、Robert M. Moriarty、Robert J. Gordon

  DOI：10.1021/ja00398a046

  日期：1981.4

  the net result of many chiral centers is optical yields approaching 100%. Finally, we suggest a method for increasing optical yields in asymmetric induction for natural product synthesis. Where a concerted reaction is involved in the synthesis, we may study the effect of individual chiral prosthetic groups at different sites in the molecule and predict which combination will lead to the highest optical

  许多手性中心的最终结果是光学产率接近 100%。最后，我们提出了一种在天然产物合成的不对称诱导中增加光学产率的方法。在合成中涉及协同反应的情况下，我们可以研究分子中不同位点的单个手性辅基的影响，并预测哪种组合将导致最高的光学产率。因此，我们可以在不依赖偶然性的情况下系统地改进非对称归纳。
• Structural evidence for the existence of a symmetrical high energy species in the degenerate vinylcyclopropane rearrangement
  作者：M. Robert Willcott、Virgil H. Cargle

  DOI：10.1021/ja01043a062

  日期：1969.7
• Infrared multiphoton induced isomerization of <i>cis</i>‐3,4‐ dichlorocyclobutene. I. Experimental results
  作者：Nathan Presser、Chung‐Rei Mao、Robert M. Moriarty、Robert J. Gordon

  DOI：10.1063/1.444618

  日期：1983.5.15

  The yield and product distribution in the laser-induced isomerization of cis-3,4-dichlorocyclobutene (DCCB) have been measured as functions of laser fluence, DCCB pressure, and buffer gas pressure. Both Woodward–Hoffman allowed and ‘‘forbidden’’ isomers were observed. The fraction of ‘‘forbidden’’ products was found to increase linearly with fluence above a threshold of 3.5 J/cm2. At high fluence the yield increased quadratically with neat DCCB pressure. Both the yield and fraction of ‘‘forbidden’’ products declined monotonically with buffer gas pressure. These observations are explained in terms of a two-channel mechanism, in which the allowed isomer is formed in a concerted path and the forbidden isomers are produced from a diradical intermediate in a nonconcerted reaction.
• Stereochemistry of Dehydrogenation of 1,4,-Cyclohexadiene with 2,3-Dichloro-5,6-dicyano-<i>p</i>-benzoquinone
  作者：Paul Müller、Daniel Joly、François Mermoud

  DOI：10.1002/hlca.19840670113

  日期：1984.2.1

  cis- and trans-(3,6-D2)-1,4-cyclohexadienes 1a and 1b have been synthesized from cis-3,4-dichlorocyclobutene (5). Aromatization to benzene with DDQ is cis-stereospecific with an uncertainty of 5%. This result is discussed in relation to concerted or stepwise mechanisms for aromatization of 1,4-dihydroaromatics with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ).

  由顺-3，4-二氯环丁烯（5）合成了顺-和反-（3，6-D 2）-1，4-环己二烯1a和1b。用DDQ芳香化为苯是顺式立体特异性的，不确定度为5％。讨论了有关用2,3-二氯-5,6-二氰基对苯醌（DDQ）进行1,4-二氢芳烃芳构化的协同或逐步机理的结果。
• MUELLER, P.;JOLY, D.;MERMOUD, F., HELV. CHIM. ACTA, 1984, 67, N 1, 105-112
  作者：MUELLER, P.、JOLY, D.、MERMOUD, F.

  DOI：——

  日期：——