2-Chloro-3-(4-bromphenyl)propiononitril | 17849-33-1

• 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-Chloro-3-(4-bromphenyl)propiononitril
• 英文别名: 3-(4-bromo-phenyl)-2-chloro-propionitrile；3-(4-Brom-phenyl)-2-chlor-propionitril；4-Bromo-I+/--chlorobenzenepropanenitrile；3-(4-bromophenyl)-2-chloropropanenitrile
• CAS: 17849-33-1
• 化学式: C₉H₇BrClN
• 分子量: 244.518
• InChiKey: QSOBNUHONIXGBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Chloro-3-(4-bromphenyl)propiononitril 、 氢化铝锂 、 溶剂黄146 、 盐酸 以68%的产率得到
  参考文献：
  名称：

  BERNAT J., CHEM. ZVESTI, 1979, 33, NO 5, 656-662

  摘要：

  DOI：
• 作为产物：
  描述：

  4-bromo-benzenediazonium ion 、 丙烯腈 在 magnesium oxide 、 丙酮 、 copper dichloride 作用下， 生成 2-Chloro-3-(4-bromphenyl)propiononitril
  参考文献：
  名称：

  Dombrowskii et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3346,3347; engl. Ausg. S. 3381

  摘要：

  DOI：

文献信息

• Arenediazonium tetrachlorocuprates(II). Modification of the Meerwein and Sandmeyer reactions
  作者：Mykola D. Obushak、Mykhaylo B. Lyakhovych、Mykola I. Ganushchak

  DOI：10.1016/s0040-4039(98)02165-0

  日期：1998.12

  In the copper-catalysed reactions of arenediazonium chlorides with unsaturated compounds arenediazonium tetrachlorocuprates(II) are formed as intermediates. A general method of preparation of these complexed diazonium salts is described. In polar solvents these salts undergo chlorinative dediazoniation to give chloroarenes in high yield. The reaction of an arenediazonium tetrachlorocuprate(II) with

  在铜催化的壬二鎓氯化物与不饱和化合物的铜催化反应中，形成了四氯铜鎓（II）间二氮杂鎓。描述了这些络合的重氮盐的一般制备方法。在极性溶剂中，这些盐会进行氯化脱重氮反应，从而以高收率得到氯代芳烃。芳烯二鎓四氯铜酸酯（II）与活化的烯烃的反应产生与Meerwein反应相同的产物。提出了用于该反应的自由基阳离子机理。
• ——
  作者：N. D. Obushak、M. B. Lyakhovich、E. E. Bilaya

  DOI：10.1023/a:1015394423091

  日期：——

  Chloroarylation of unsaturated compounds with arenediazonium chlorides in the presence of CuCl2 as catalyst involves intermediate formation of arenediazonium tetrachlorocuprates(II) [ArN2+](2) CuCl42-. A procedure for preparative isolation of these intermediates was developed, and they were shown to be efficient arylating agents. Reactions of [ArN2+](2) CuCl42- with unsaturated compounds gave the corresponding Meerwein products; a mechanism was proposed for these reactions. In polar solvents arenediazonium tetrachlorocuprates(II) are converted into chloroarenes, presumably through a cyclic transition state.
• A Modular Dual‐Catalytic Aryl‐Chlorination of Alkenes
  作者：Bo Li、Ala Bunescu、Daniel Drazen、Katherine Rolph、Jean Michalland、Matthew J. Gaunt

  DOI：10.1002/anie.202405939

  日期：2024.8.19

  Alkyl chlorides are a class of versatile building blocks widely used to generate C(sp3)‐rich scaffolds through transformation such as nucleophilic substitution, radical addition reactions and metal‐catalyzed cross‐coupling processes. Despite their utility in the synthesis of high‐value functional molecules, distinct methods for the preparation of alkyl chlorides are underrepresented. Here, we report a visible‐light‐mediated dual catalysis strategy for the modular synthesis of highly functionalized and structurally diverse arylated chloroalkanes via the coupling of diaryliodonium salts, alkenes and potassium chloride. A distinctive aspect of this transformation is a ligand‐design‐driven approach for the development of a copper(II)‐based atom‐transfer catalyst that enables the aryl‐chlorination of electron‐poor alkenes, complementing its iron(III)‐based counterpart that accommodates non‐activated aliphatic alkenes and styrene derivatives. The complementarity of the two dual catalytic systems allows the efficient aryl‐chlorination of alkenes bearing different stereo‐electronic properties and a broad range of functional groups, maximizing the structural diversity of the 1‐aryl, 2‐chloroalkane products.