N-(2,4-dichlorobenzylidene)-1-(2,4-dichlorophenyl)methylamine | 122184-54-7

• 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-(2,4-dichlorobenzylidene)-1-(2,4-dichlorophenyl)methylamine
• 英文别名: N-(2,4-dichlorobenzylidene)-2,4-dichlorophenylmethylamine；N-(2,4-dichlorobenzyl)-1-(2,4-dichlorophenyl)methanimine；N-(2,4-dichlorobenzyl)-2,4-dichlorobenzaldimine；benzylamine；1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methyl]methanimine
• CAS: 122184-54-7
• 化学式: C₁₄H₉Cl₄N
• 分子量: 333.044
• InChiKey: LKHZOKZRZRQKDT-UHFFFAOYSA-N

物化性质

• 沸点：
  420.7±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲胺 在 Iron(III) nitrate nonahydrate 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以71%的产率得到N-(2,4-dichlorobenzylidene)-1-(2,4-dichlorophenyl)methylamine
  参考文献：
  名称：

  铁催化的胺或醇和胺在空气下的需氧氧化反应直接合成亚胺

  摘要：

  通过直接使用空气作为经济和安全的氧化剂，大量廉价的铁很容易催化伯胺，仲胺，苄胺与苯胺的氧化反应和醇与胺的氧化反应，为制备有用的化合物提供了几种直接，实用和绿色的方法亚胺。

  DOI：

  10.1021/ol4010118

文献信息

• Cu(I)/TEMPO-catalyzed aerobic oxidative synthesis of imines directly from primary and secondary amines under ambient and neat conditions
  作者：Bo Huang、Haiwen Tian、Shoushuai Lin、Meihua Xie、Xiaochun Yu、Qing Xu

  DOI：10.1016/j.tetlet.2013.03.098

  日期：2013.5

  By catalyst and condition screening, a simple Cu(I)/TEMPO-catalyst system was found to be an active and highly effective catalyst for the aerobic oxidation of amines to imines in open air at room temperature under neat conditions. This new method provided a mild, efficient, and practical alternative for the synthesis of the useful imines directly from primary and secondary amines.

  通过催化剂和条件筛选，发现一种简单的Cu（I）/ TEMPO-催化剂体系是一种在室温和纯净条件下，在露天条件下将胺有氧氧化为亚胺的活性和高效催化剂。这种新方法为直接从伯胺和仲胺合成有用的亚胺提供了温和，有效和实用的替代方法。
• Selective aerobic oxidation of halides and amines with an inorganic-ligand supported zinc catalyst
  作者：Jingjing Wang、Yongyan Zhai、Ying Wang、Han Yu、Wenshu Zhao、Yongge Wei

  DOI：10.1039/c8dt03003k

  日期：——

  A practical, efficient and environmentally benign catalytic protocol for the oxidative cross-coupling reaction of halides with amines, oxidative self-coupling of amines and oxidation of halides was developed with inorganic-ligand supported ZnPOM (NH4)4[ZnMo6O18(OH)6] using molecular oxygen. This method mainly utilizes an inorganic polymolybdate ligand to support the Zn2+ ion, avoiding the use of complicated

  利用无机配体负载的ZnPOM（NH 4）4 [ZnMo 6 O 18（ OH）6 ]使用分子氧。该方法主要利用无机多钼酸盐配体来支撑Zn 2+离子，避免了使用复杂的有机配体。
• Convenient and clean synthesis of imines from primary benzylamines
  作者：Guobiao Chu、Chunbao Li

  DOI：10.1039/c0ob00043d

  日期：——

  The current syntheses of imines from benzylamines are often performed in organic solvents or under harsh reaction conditions. Clean oxidation of primary benzylamines to imines has been successfully achieved using H2O2 in water at room temperature catalyzed by V2O5. Among the 10 imine products, 5 of them precipitated from the reaction and led pure products after simple filtration. No organic solvents are needed in the whole process. The yields are good to quantitative. This represents an efficient and green procedure of the synthesis of imines. A similar green oxidation of benzylamines to aromatic aldehydes is also reported. A benzylic anion-involved mechanism is proposed based on the experiments.

  目前，从苄胺合成亚胺的合成通常在有机溶剂中或在苛刻的反应条件下进行。使用H2O2在水中室温下催化生成亚胺的初级苄胺的清洁氧化已成功实现，催化剂为V2O5。在10种亚胺产物中，5种从反应中沉淀出来，并通过简单过滤得到纯产品。整个过程中不需要有机溶剂。产率良好，接近定量。这代表了一种有效且绿色的亚胺合成程序。还有类似的苄胺向芳香醛的绿色氧化也有报道。根据实验提出了一种涉及苄基阴离子的机制。
• Iron-Catalyzed Direct Synthesis of Imines from Amines or Alcohols and Amines via Aerobic Oxidative Reactions under Air
  作者：Erlei Zhang、Haiwen Tian、Sendong Xu、Xiaochun Yu、Qing Xu

  DOI：10.1021/ol4010118

  日期：2013.6.7

  Abundant and cheap iron readily catalyzed the aerobic oxidative reactions of primary amines, secondary amines, benzylamines with anilines, and alcohols with amines by directly using air as the economic and safe oxidant, providing several direct, practical, and greener approaches for the preparation of useful imines.

  通过直接使用空气作为经济和安全的氧化剂，大量廉价的铁很容易催化伯胺，仲胺，苄胺与苯胺的氧化反应和醇与胺的氧化反应，为制备有用的化合物提供了几种直接，实用和绿色的方法亚胺。
• Selective Formation of Imines by Aerobic Photocatalytic Oxidation of Amines on TiO₂
  作者：Xianjun Lang、Hongwei Ji、Chuncheng Chen、Wanhong Ma、Jincai Zhao

  DOI：10.1002/anie.201007056

  日期：2011.4.18

  An oxygenation pathway: The title transformation involves a two‐step process: a selective oxygenation step to generate aldehyde intermediates and a subsequent condensation step to afford the imine products (see scheme).

  氧化途径：标题转化涉及两步过程：选择性的氧化步骤以生成醛中间体，以及随后的缩合步骤以提供亚胺产物（参见方案）。