4-[2-(4-氯苯基)乙基]苯甲腈 | 10270-28-7

• 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: 4-[2-(4-氯苯基)乙基]苯甲腈
• 英文名称: 4-(2-(4'-chlorophenyl)ethyl)benzonitrile
• 英文别名: 4-(4-chlorophenethyl)benzonitrile；4-(4-Chlor-phenaethyl)-benzonitril；4-[2-(4-Chlorophenyl)ethyl]benzonitrile
• CAS: 10270-28-7
• 化学式: C₁₅H₁₂ClN
• 分子量: 241.72
• InChiKey: WLOMDOBWKSANPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-氯-4-(2-碘乙基)-苯 在 N,N-二甲基乙酰胺 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride 、 四丁基溴化铵 作用下， 反应 8.0h， 生成 4-[2-(4-氯苯基)乙基]苯甲腈
  参考文献：
  名称：

  锌的机械化学活化及其在根岸交叉偶联中的应用

  摘要：

  据报道，锌的形式独立活化，同时产生有机锌物质，并通过机械化学方法参与根岸交叉偶联反应。报道的方法对 C(sp 3 )–C(sp 2 ) 和 C(sp 2 )–C(sp 2 ) 偶联表现出广泛的底物范围，并且对许多重要的官能团具有耐受性。该方法可以为从贱金属原位生成有机金属化合物及其通过机械化学方法参与合成反应提供广泛的机会。

  DOI：

  10.1002/anie.201806480

文献信息

• A Ball-Milling-Enabled Cross-Electrophile Coupling
  作者：Andrew C. Jones、William I. Nicholson、Jamie A. Leitch、Duncan L. Browne

  DOI：10.1021/acs.orglett.1c02096

  日期：2021.8.20

  cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is herein described. Under a mechanochemical manifold, the reductive C–C bond formation was achieved in the absence of bulk solvent and air/moisture sensitive setups, in reaction times of 2 h. The mechanical action provided by ball milling permits the use of a range of zinc sources to turnover the nickel catalytic cycle, enabling

  本文描述了通过球磨实现的芳基卤化物和烷基卤化物的镍催化交叉亲电偶联。在机械化学歧管下，在没有本体溶剂和空气/水分敏感设置的情况下，在 2 小时的反应时间内实现了还原性 C-C 键的形成。球磨提供的机械作用允许使用一系列锌源来翻转镍催化循环，从而合成 28 种交叉亲电子偶联产物。
• Addition of aryl radicals generated from electrochemical reduction of aryl halides on carbon-carbon double bonds.
  作者：Zoubida Chami、Monique Gareil、Jean Pinson、Jean-Michel Saveant、André Thiebault

  DOI：10.1016/s0040-4039(00)80170-7

  日期：——

  Aryl radicals generated by electrochemical reduction of aryl halides in aprotic medium react with styrene and its derivatives to give arylated addition compounds.

  在非质子介质中通过电化学还原芳基卤化物生成的芳基与苯乙烯及其衍生物反应，生成芳基化加成化合物。
• Aryl radicals from electrochemical reduction of aryl halides. Addition on olefins
  作者：Zoubida Chami、Monique Gareil、Jean Pinson、Jean Michel Saveant、Andre Thiebault

  DOI：10.1021/jo00002a020

  日期：1991.1

  Aryl radicals generated by direct and indirect (by means of an aromatic anion radical mediator) electrochemistry are reacted with olefins in liquid ammonia and in organic solvents (Me2SO, MeCN, DMF). The arylated product is obtained in good yield in the latter case. In pure liquid NH3, the yields are extremely poor. They are improved upon addition of a proton donor such as urea or water; further increase of yields is obtained upon addition of 2-propanol. A reaction mechanism is proposed based on these observations and on the results of deuterium incorporation experiments. Cyclic voltammetry is used to determine the rate constant of the key step in the mechanism, viz, the addition of the aryl radical to the olefin, through its competition with its reaction with nucleophiles in the framework of an S(RN)1 substitution process.
• 10.1016/j.mcat.2024.114228
  作者：Wang, Mingchun、Song, Ao、Wang, Xiupeng、Xiong, Qingchen、Li, Zhaopeng、Shen, Xiangyan、Wang, Rongzhou、Cong, Hailin

  DOI：10.1016/j.mcat.2024.114228

  日期：——
• Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling
  作者：Qun Cao、Joseph L. Howard、Emilie Wheatley、Duncan L. Browne

  DOI：10.1002/anie.201806480

  日期：2018.8.27

  A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross‐coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation

  据报道，锌的形式独立活化，同时产生有机锌物质，并通过机械化学方法参与根岸交叉偶联反应。报道的方法对 C(sp 3 )–C(sp 2 ) 和 C(sp 2 )–C(sp 2 ) 偶联表现出广泛的底物范围，并且对许多重要的官能团具有耐受性。该方法可以为从贱金属原位生成有机金属化合物及其通过机械化学方法参与合成反应提供广泛的机会。