2,4-dichlorophenylethynyl chloride | 1313869-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dichlorophenylethynyl chloride
• 英文别名: 2,4-Dichloro-1-(2-chloroethynyl)benzene
• CAS: 1313869-14-5
• 化学式: C₈H₃Cl₃
• 分子量: 205.471
• InChiKey: APGCWGRHKRPJBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• 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

反应信息

• 作为反应物：
  描述：

  2,4-dichlorophenylethynyl chloride 在 1,5-cis,cis-cyclooctadiene 、 bis(η3-allyl-μ-chloropalladium(II)) 、 溶剂黄146 、 lithium chloride 作用下， 反应 4.0h， 以90%的产率得到2,4-dichloro-1-[(Z)-1,2-dichloroethenyl]benzene
  参考文献：
  名称：

  Highly stereoselective synthesis of (Z)-1,2-dihaloalkenes by a Pd-catalyzed hydrohalogenation of alkynyl halides

  摘要：

  一种前所未有的钯催化的炔基卤化物的氢卤化反应已经实现，能够区域和立体选择性合成（Z）-1,2-二卤烯，使用的催化剂为[(烯丙基)PdCl]2，配体为顺,顺-1,5-环辛二烯。该方法的优势通过迭代交叉偶联反应组装三取代的（Z）-烯炔和通过串联的Diels–Alder–芳构化反应组装多功能苯烃得到了很好的体现。

  DOI：

  10.1039/c2cc31553j

文献信息

• Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio- and Stereoselective Synthesis of (<i>Z</i>)-β-Haloenol Acetates
  作者：Xiaoyi Chen、Dongxu Chen、Zenghui Lu、Lichun Kong、Gangguo Zhu

  DOI：10.1021/jo2005318

  日期：2011.8.5

  Pd-catalyzed coupling of haloalkynes with allyl acetate has been reported, providing a convenient method for the stereoselective synthesis of (Z)-β-haloenol acetates in good yields. The synthetic utility of this method is demonstrated by the formation of functionalized enol acetates via the Suzuki–Miyaura or Sonogashira coupling of the resulting (Z)-β-haloenol acetate products.

  已经报道了钯催化卤代炔烃与乙酸烯丙酯的偶联，为以高收率立体选择性合成（Z）-β-卤代烯醇乙酸酯提供了便利的方法。该方法的合成实用性通过生成的（Z）-β-卤代烯醇乙酸酯产物的Suzuki-Miyaura或Sonogashira偶联形成官能化的烯醇乙酸酯得到证明。
• Au-Catalyzed Addition of Nucleophiles to Chloroalkynes: A Regio- and Stereoselective Synthesis of (<i>Z</i> )-Alkenyl Chlorides
  作者：Congrong Liu、Yunbo Xue、Lianghui Ding、Haiyun Zhang、Fulai Yang

  DOI：10.1002/ejoc.201801222

  日期：2018.12.13

  developed for the regio‐ and stereoselective synthesis of (Z)‐alkenyl chlorides via the gold‐catalyzed addition between chloroalkynes and protic nucleophiles. A broad range of protic nucleophiles smoothly react with aromatic, vinylic, or aliphatic chloroalkynes to afford various functionalized (Z)‐alkenyl chlorides with high to excellent yields and extremely high stereoselectivity.

  已经开发了一种协议，用于通过在氯炔烃和质子亲核试剂之间进行金催化的加成反应来合成（Z）-烯基氯化物的区域和立体选择性合成。各种各样的质子亲核试剂可与芳族，乙烯基或脂族氯炔烃平稳反应，从而以高到极好的收率和极高的立体选择性提供各种官能化的（Z）-烯基氯化物。
• Synthesis of cis-1,2-dichlorovinylsulfones via Fe-catalyzed regio- and stereoselective addition of sulfonyl chlorides to aromatic chloroalkynes
  作者：Lina Wang、Hui Zhu、Jianwei Che、Yuanfa Yang、Gangguo Zhu

  DOI：10.1016/j.tetlet.2013.12.063

  日期：2014.1

  An iron-catalyzed regio- and stereoselective chlorosulfonylation of aryl chloroalkynes has been described, producing cis-1,2-dichlorovinylsulfones in satisfactory yields with good to excellent stereoselectivity (Z/E up to 95:5). A variety of functional groups such as F, NO2, Cl, Br, OMe, and t-Bu are found to be compatible under the reaction conditions. (C) 2013 Elsevier Ltd. All rights reserved.