N-[(2-chlorophenyl)methylene]benzamine | 32347-02-7

• 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-chlorophenyl)methylene]benzamine
• 英文别名: N-[(2-chlorophenyl)methylene]-benzeneamine；(E)-1-(2-chlorophenyl)-N-phenylmethanimine；N-[(E)-(2-chlorophenyl)methylene]aniline；(E)-N-(2-chlorobenzylidene)aniline；o-chlorobenzylideneaniline；((E)-2-chloro-benzyliden)-aniline；2-Chlor-benzaldehyd-(E)-phenylimin
• CAS: 32347-02-7
• 化学式: C₁₃H₁₀ClN
• 分子量: 215.682
• InChiKey: BIXVUZSUHIDQQJ-XNTDXEJSSA-N

物化性质

• 熔点：
  26.5 °C
• 沸点：
  154 °C(Press: 1.5 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-[(2-chlorophenyl)methylene]benzamine 生成 2-Anilino-2-(2-chlorophenyl)acetic acid
  参考文献：
  名称：

  KATO, SHOZO

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氯苄醇 、 苯胺 在 potassium tert-butylate 、 C₁₁H₇BrMnN₃O₃ 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N-[(2-chlorophenyl)methylene]benzamine
  参考文献：
  名称：

  A Highly Selective Manganese-Catalyzed Synthesis of Imines under Phosphine-Free Conditions

  摘要：

  An efficient and highly selective phosphine-free NN-manganese(I) complex catalyst system was developed for the acceptorless dehydrogenative coupling of alcohols with amines to form imines. The coupling reactions underwent at 3 mol % catalyst loading, and a large range of alcohols and amines with diverse functional groups was applied, including challenging diol and diamine. The target imine products were obtained in good to excellent yields. The present work provides an alternative method to construct highly active nonprecious metal complex catalysts based on phosphine-free ligands.

  DOI：

  10.1021/acs.organomet.9b00769

文献信息

• Stereoselective Peterson Olefinations from Bench-Stable Reagents and<i>N</i>-Phenyl Imines
  作者：Manas Das、Atul Manvar、Maïwenn Jacolot、Marco Blangetti、Roderick C. Jones、Donal F. O'Shea

  DOI：10.1002/chem.201500475

  日期：2015.6.8

  The synthesis of bench‐stable α,α‐bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (E/Z ∼1:1 to 4:1) though this was significantly improved by employing the corresponding substituted N‐benzylideneaniline (up to 99:1)

  描述了台稳的α，α-双（三甲基甲硅烷基）甲苯和三（三甲基甲硅烷基）甲烷的合成，并已在较宽的底物范围内实现了它们在立体选择性Peterson烯烃中的应用。羰基亲电试剂的产物立体选择性差（E / Z约为1：1至4：1），尽管通过使用相应的取代N-苄叉基苯胺（最高达99：1）作为替代亲电试剂可以显着改善。烯化副产物被鉴定为N，N-双（三甲基甲硅烷基）苯胺，很容易通过酸水萃取从产物中分离出来。已经获得了自催化循环的证据。
• Ligand‐Controlled Copper‐Catalyzed Regiodivergent Carbonylative Synthesis of α‐Amino Ketones and α‐Boryl Amides from Imines and Alkyl Iodides
  作者：Fu‐Peng Wu、Xiao‐Feng Wu

  DOI：10.1002/ange.202012251

  日期：2021.1.11

  AbstractRegioselective transformation is among the long‐standing challenges in organic synthesis. In this communication, a copper‐catalyzed selectivity controlled regiodivergent borocarbonylation of imines with alkyl iodides has been developed. Various α‐amino ketones and α‐boryl amides were produced in moderate to good yields from the same substrates. The choice of the ligand is key for the regioselectivity

  摘要区域选择性转化是有机合成中长期存在的挑战之一。在这篇通讯中，开发了一种铜催化选择性控制的亚胺与烷基碘的区域发散硼羰基化反应。从相同的底物中可以以中等至良好的产率生产各种 α-氨基酮和 α-硼基酰胺。配体的选择是区域选择性控制的关键：用（p‐CF3C6H4）3P作为配体，而相应的α-硼酰胺在使用时具有高区域选择性我IMes作为配体。
• Very Mild, Enantioselective Synthesis of Propargylamines Catalyzed by Copper(I)−Bisimine Complexes
  作者：Federica Colombo、Maurizio Benaglia、Simonetta Orlandi、Fabio Usuelli、Giuseppe Celentano

  DOI：10.1021/jo052481g

  日期：2006.3.1

  was studied. The reaction is catalyzed by copper complexes of enantiomerically pure bisimines, readily prepared in very high yields from the commercially available binaphthyl diamine. A very simple experimental procedure allowed to obtain at room temperature optically active propargylamines in high yields and enantioselectivity. Interestingly, bisimine/copper(I) complexes were able to promote the direct

  研究了芳基和烷基乙炔衍生物向亚胺的立体选择性加成。该反应由对映体纯的双亚胺的铜络合物催化，该双配合物很容易以很高的收率由市售的联萘二胺制备。一个非常简单的实验程序可以在室温下以高收率和对映选择性获得光学活性的炔丙基胺。有趣的是，双亚胺/铜（I）配合物能够促进对烷基乙炔亚胺的直接，对映选择性，催化加成。研究了催化剂负载量和其他反应参数对转化的立体化学结果的影响。极为方便的方法，温和的反应条件，
• Fast and Efficient Synthesis of Pyrano[3,2-<i>c</i>]quinolines Catalyzed by Niobium(V) Chloride
  作者：Mauricio Constantino、Luiz da Silva-Filho、Valdemar Lacerda Júnior、Gil da Silva

  DOI：10.1055/s-2008-1067186

  日期：2008.8

  A highly efficient two-step method for the synthesis of pyranoquinoline derivatives from imino-Diels-Alder reactions between aldimines and 3,4-dihydro-2H-pyran using niobium(V) chloride as catalyst under mild conditions is described.

  报道了一种高效的两步法，通过在温和条件下使用五氯化铌作为催化剂，由醛亚胺和3,4-二氢-2H-吡喃之间的亚胺狄尔斯-阿尔德反应合成吡喃并喹啉衍生物。
• Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines
  作者：Xiaoying Zhang、Junhua Zhang、Zhiqiang Hao、Zhangang Han、Jin Lin、Guo-Liang Lu

  DOI：10.1021/acs.organomet.1c00552

  日期：2021.11.22

  characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine

  水杨醛配体的治疗L1H - L2H（L1H = 2,4-二-叔丁基-6 - （（喹啉-8-基亚氨基）甲基）苯酚; L2H = 2,4-二-叔丁基-6 - （（ (2-(二乙氨基)乙基)亚氨基)甲基)苯酚)与Ni(OAc) 2 ·4H 2 O在乙醇回流中得到镍配合物[( L1 )Ni(OAc)]( 1 )和[( L2 )Ni(OAc) )] ( 2 ) 分别。的反应L3H（L3H =（2,4-二-叔丁基-6 - （（（2-（吡啶-2-基）乙基）亚氨基）甲基）苯酚）），与镍（OAC）2 ·4H 2在过量三乙胺存在下，O 得到双配体配位的镍配合物 [( L2 ) 2 Ni] ( 3 )。配合物1 - 3分别充分表征通过高分辨率质谱法，红外光谱，元素分析，X-射线衍射分析。所有三种 Ni(II) 配合物在醇和胺的无受体脱氢偶联生成亚胺和二亚胺方面均表现出有效的活性和良好的选择性。本协议通过使用地球

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