N-[1-(4-chlorophenyl)propyl]phenylamine | 22920-62-3

• 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: N-[1-(4-chlorophenyl)propyl]phenylamine
• 英文别名: N-[1-(4-chlorophenyl)propyl]aniline
• CAS: 22920-62-3
• 化学式: C₁₅H₁₆ClN
• 分子量: 245.752
• InChiKey: MOGKQOQJQFPPMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯苯丙酮 在 (2S)-1-formyl-N-Ph-piperazine-2-carboxamide-based reagent 、 4 A molecular sieve 、 三氯硅烷 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 60.0h， 生成 N-[1-(4-chlorophenyl)propyl]phenylamine
  参考文献：
  名称：

  1-哌嗪-2-羧酸衍生的N-甲酰胺，是一种高度对映选择性的路易斯碱性催化剂，用于N-芳基亚胺的氢化硅烷化，具有前所未有的底物特性。

  摘要：

  [反应：见正文] 1-哌嗪-2-羧酸衍生的N-甲酰胺已被开发为高度对映选择性的Lewis碱性催化剂，用于N-芳基亚胺与三氯硅烷的氢化硅烷化反应。发现N 4上的芳烃磺酰基对于催化剂的高对映选择性是至关重要的。对于包括芳香族和脂肪族酮亚胺在内的多种底物，特别是那些具有相对较大烷基的R（2）的底物，均获得了高分离产率（高达99％）和对映选择性（高达97％）。

  DOI：

  10.1021/ol060984i

文献信息

• Cerium(IV)-Promoted Ethylation of Schiff Bases by Triethylaluminum
  作者：Jochanan Blum、Dmitry Tsvelikhovsky、Herbert Schumann

  DOI：10.1055/s-2006-942379

  日期：2006.6

  Schiff bases Ar1CH=NAr2 that are refractory towards Et3Al are activated at room temperature by cerium(IV) compounds. The ethylation takes place selectively at the methine moiety of the imine. The process is strongly influenced by steric hindrance and depends on the electronic nature of the substrate: electron-donating substituents promote the reaction while electron-withdrawing groups cause it to slow down. Application of cerium(IV) ammonium nitrate as promoter gives the best results. In the absence of excess Et3Al it causes, however, transformation of the Schiff base to the corresponding aldehydes and amines.

  铈（IV）化合物可在室温下激活对 Et3Al 具有耐受性的希夫碱 Ar1CH=NAr2。乙化作用选择性地发生在亚胺的甲基上。这一过程受到立体阻碍的强烈影响，并取决于底物的电子性质：供电子的取代基会促进反应，而抽电子的基团则会导致反应减慢。使用硝酸铵铈（IV）作为促进剂能产生最佳效果。不过，在没有过量 Et3Al 的情况下，它会导致希夫碱转化为相应的醛和胺。
• Diethylzinc: A Chain-Transfer Agent in Intermolecular Radical Additions. A Parallel with Triethylborane
  作者：Michèle P. Bertrand、Laurence Feray、Robert Nouguier、P. Perfetti

  DOI：10.1021/jo9912404

  日期：1999.12.1

  In the presence of oxygen, diethylzinc can be used to promote radical additions to C=N bond containing radical accepters and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reactions is established. The methodology is restricted to secondary and tertiaryalkyl radicals generated from the corresponding alkyl iodides. It could not be extended either to C=C bond containing radical accepters such as methyl methacrylate and nitrocyclohexene or to diethylazodicarboxylate.
• Lanthanide-Promoted Ethylation of Schiff Bases by Triethylaluminum
  作者：Dmitry Tsvelikhovsky、Dmitri Gelman、Gary A. Molander、Jochanan Blum

  DOI：10.1021/ol049420+

  日期：2004.6.1

  Schiff bases of aromatic aldehydes and anilines that fail to react with triethylaluminum are smoothly alkylated at room temperature in the presence of lanthanide catalysts. The alkylation takes place selectively at the vinylic carbon atom.
• Addition of diethylzinc to imines promoted by Lewis acid
  作者：Xue Long Hou、Xiao Lan Zheng、Li Xin Dai

  DOI：10.1016/s0040-4039(98)01442-7

  日期：1998.9

  The alkylation of imines by using diethylzinc reagent in the presence of Lewis acid afforded secondary amines in high yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• <scp>l</scp>-Piperazine-2-carboxylic Acid Derived <i>N</i>-Formamide as a Highly Enantioselective Lewis Basic Catalyst for Hydrosilylation of <i>N</i>-Aryl Imines with an Unprecedented Substrate Profile
  作者：Zhouyu Wang、Mounuo Cheng、Pengcheng Wu、Siyu Wei、Jian Sun

  DOI：10.1021/ol060984i

  日期：2006.7.1

  l-Piperazine-2-carboxylic acid derived N-formamides have been developed as highly enantioselective Lewis basic catalysts for the hydrosilylation of N-aryl imines with trichlorosilane. The arene sulfonyl group on N4 was found to be critical for the high enantioselectivity of the catalyst. High isolated yields (up to 99%) and enantioselectivities (up to 97%) were obtained for a broad range of substrates, including

  [反应：见正文] 1-哌嗪-2-羧酸衍生的N-甲酰胺已被开发为高度对映选择性的Lewis碱性催化剂，用于N-芳基亚胺与三氯硅烷的氢化硅烷化反应。发现N 4上的芳烃磺酰基对于催化剂的高对映选择性是至关重要的。对于包括芳香族和脂肪族酮亚胺在内的多种底物，特别是那些具有相对较大烷基的R（2）的底物，均获得了高分离产率（高达99％）和对映选择性（高达97％）。