1-(1-氯-2-苯基乙基)-4-甲基苯 | 22692-62-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(1-氯-2-苯基乙基)-4-甲基苯
• 英文名称: 1-p-tolyl-2-phenylethyl chloride
• 英文别名: α-Chlor-4-methyl-dibenzyl；1-(1-Chloro-2-phenylethyl)-4-methylbenzene
• CAS: 22692-62-2
• 化学式: C₁₅H₁₅Cl
• 分子量: 230.737
• InChiKey: JHJSWMRGVCPITM-UHFFFAOYSA-N

物化性质

• 沸点：
  315.7±11.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-(1-氯-2-苯基乙基)-4-甲基苯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 1-甲基-4-((e)-苯乙烯)-苯
  参考文献：
  名称：

  乙醇钠促进乙醇中1,2-二芳基-1-氯乙烷的消除反应。α-和β-苯基取代基的动力学效应

  摘要：

  研究了乙醇钠促进乙醇中几种取代的1,2-二芳基-1-氯乙烷的消除反应动力学。根据β-苯基取代基的动力学效应，已计算出+ 2·26的ρ值。该值比从取代的苯乙基氯的相应消除中发现的（+ 2·50）略低，因此表明在消除反应中引入α-苯基基本上不会改变过渡态的碳负离子特性。 β-苯基活化的底物。对于α-苯基取代基观察到小的动力学效应。吸电子的α-苯基取代基可提高反应速率：β处于过渡状态。

  DOI：

  10.1039/p29750000329
• 作为产物：
  描述：

  1-(4-甲基苯基)-2-苯基乙醇 在 氯化亚砜 作用下， 生成 1-(1-氯-2-苯基乙基)-4-甲基苯
  参考文献：
  名称：

  乙醇钠促进乙醇中1,2-二芳基-1-氯乙烷的消除反应。α-和β-苯基取代基的动力学效应

  摘要：

  研究了乙醇钠促进乙醇中几种取代的1,2-二芳基-1-氯乙烷的消除反应动力学。根据β-苯基取代基的动力学效应，已计算出+ 2·26的ρ值。该值比从取代的苯乙基氯的相应消除中发现的（+ 2·50）略低，因此表明在消除反应中引入α-苯基基本上不会改变过渡态的碳负离子特性。 β-苯基活化的底物。对于α-苯基取代基观察到小的动力学效应。吸电子的α-苯基取代基可提高反应速率：β处于过渡状态。

  DOI：

  10.1039/p29750000329

文献信息

• Palladium-Catalyzed Oxidative Arylhalogenation of Alkenes: Synthetic Scope and Mechanistic Insights
  作者：Dipannita Kalyani、Andrew D. Satterfield、Melanie S. Sanford

  DOI：10.1021/ja101851v

  日期：2010.6.23

  This article describes the development of a Pd-catalyzed reaction for the arylhalogenation (halogen = Cl or Br) of diverse alpha-olefins by oxidatively intercepting Mizoroki-Heck intermediates. These transformations afford synthetically useful 1,2- and 1,1-arylhalogenated products in good yields with good to excellent selectivities that can be modulated by changing the nature of the halogenating reagent and/or the reaction conditions. The selectivity of these reactions can be rationally tuned by (i) controlling the relative rates of oxidative functionalization versus beta-hydride elimination from equilibrating Pd-II-alkyl species and (ii) stabilization of organometallic Pd-II intermediates through the formation of pi-benzyl adducts. These arylhalogenations exhibit modest to excellent levels of stereoselectivity, and the key carbon-halogen bond-forming step proceeds with predominant retention of stereochemistry at carbon.
• Laarhoven,W.H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1967, vol. 86, p. 821 - 829
  作者：Laarhoven,W.H. et al.

  DOI：——

  日期：——
• Anantaraman,R.; Pillai,M.M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1976, vol. 14B, p. 361 - 363
  作者：Anantaraman,R.、Pillai,M.M.

  DOI：——

  日期：——
• 10.1002/anie.202405939
  作者：Li, Bo、Bunescu, Ala、Drazen, Daniel、Rolph, Katherine、Michalland, Jean、Gaunt, Matthew J.

  DOI：10.1002/anie.202405939

  日期：——

  AbstractAlkyl 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.
• Elimination reactions of 1,2-diaryl-1-chloroethanes promoted by sodium ethoxide in ethanol. The kinetic effects of α- and β-phenyl substituents
  作者：Enrico Baciocchi、Piero Perucci、Cesare Rol

  DOI：10.1039/p29750000329

  日期：——

  The kinetics of the elimination reactions of several substituted 1,2-diaryl-1-chloroethanes promoted by sodium ethoxide in ethanol have been studied. On the basis of the kinetic effects of β-phenyl substituents a ρ value of +2·26 has been calculated. This value is slightly less positive than that (+2·50) found in the corresponding elimination from substituted phenylethyl chlorides, thus showing that

  研究了乙醇钠促进乙醇中几种取代的1,2-二芳基-1-氯乙烷的消除反应动力学。根据β-苯基取代基的动力学效应，已计算出+ 2·26的ρ值。该值比从取代的苯乙基氯的相应消除中发现的（+ 2·50）略低，因此表明在消除反应中引入α-苯基基本上不会改变过渡态的碳负离子特性。 β-苯基活化的底物。对于α-苯基取代基观察到小的动力学效应。吸电子的α-苯基取代基可提高反应速率：β处于过渡状态。