(E)-N-(naphthalen-1-ylmethylene)aniline | 78569-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N-(naphthalen-1-ylmethylene)aniline
• 英文别名: (E)-1-(naphthalen-1-yl)-N-phenylmethanimine；N-(naphthalen-1-ylmethylene)phenylamine；N-([1-naphthalenyl]methylene)benzenamine
• CAS: 78569-38-7
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: WNYBWTSSOIEBMP-QGOAFFKASA-N

物化性质

• 沸点：
  400.5±14.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• 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：

  (E)-N-(naphthalen-1-ylmethylene)aniline 在 甲醇 、 silica gel 作用下， 以 neat (no solvent) 为溶剂， 反应 12.0h， 生成 N-[(1-萘基)甲基]苯胺
  参考文献：
  名称：

  亚胺的无催化剂和无溶剂简便的硼氢化反应。

  摘要：

  据报道，一种简便的方法可用于芳族和杂芳族亚胺的无催化剂和无溶剂的硼氢化反应。这种原子经济的方法具有可扩展性，可与空间和电子形式的亚胺兼容，对各种官能团均表现出优异的耐受性，并且在大多数情况下可在环境温度下有效发挥作用，水解后得到的仲胺的收率良好。

  DOI：

  10.1002/asia.201901016
• 作为产物：
  描述：

  1-萘甲醇 、 苯胺 在 potassium tert-butylate 、 C₁₁H₇BrMnN₃O₃ 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (E)-N-(naphthalen-1-ylmethylene)aniline
  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

• Synthetic and Mechanistic Studies of Indium-Mediated Allylation of Imines in Ionic Liquids
  作者：Man Chun Law、Tin Wai Cheung、Kwok-Yin Wong、Tak Hang Chan

  DOI：10.1021/jo062198x

  日期：2007.2.1

  Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium(I)

  在[bpy] [BF 4 ]（bpy = N-丁基吡啶）中，将铟粉介导的烯丙基溴与烯丙基溴烯丙基化衍生自芳基和不可烯化的脂肪族醛的醛亚胺，以得到相应的均烯丙基胺良好的收率。可以通过改变[bpy] [Br]形式的溴离子添加剂的数量来实现单烯丙基化胺的选择性形成。通过NMR光谱研究了反应中形成的瞬态有机铟中间体，烯丙基（I）和烯丙基（III）二溴化物。
• Electronic and Steric Control in Regioselective Addition Reactions of Organolithium Reagents with Enaldimines
  作者：Kiyoshi Tomioka、Yoshito Shioya、Yasuo Nagaoka、Ken-ichi Yamada

  DOI：10.1021/jo015766b

  日期：2001.10.1

  A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic alpha,beta-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nitrogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl

  衍生自萘-1-甲醛和无环α，β-不饱和醛的亚胺与有机锂试剂的反应方式取决于亚胺氮原子上取代基的特征。在氮原子上具有吸电子芳基的亚胺表现为朝向有机锂试剂的1,2-亚胺。相反，带有烷基或庞大的芳基的亚胺有利于有机锂试剂的1，4-加成。基于分子轨道计算，合理化了亚胺氮原子上取代基的电子和空间反应模式调节。
• Diarylacetylenes, enamines and acetylenic polymers and their production
  申请人：——

  公开号：US05233046A1

  公开（公告）日：1993-08-03

  Diarylacetylenes and diarylenamines are synthesized from a Schiff's base and an N-arylmethylheterocycle; these compounds are useful as intermediates for a variety of polymers; in particular an efficient process is provided for producing diaryl acetylenes useful in the efficient production of acetylene group-containing polymers which can be cross-linked to produce high strength polymers free of structural defects such as conventionally arise as a result of liberation of volatiles during the cross-linking.

  从Schiff碱和N-芳基甲基杂环化合物合成二芳基乙炔和二芳基胺；这些化合物可作为各种聚合物的中间体，特别是提供了一种高效的方法来生产二芳基乙炔，用于高效生产含乙炔基团的聚合物，这些聚合物可以交联形成高强度聚合物，不会出现结构缺陷，如传统交联过程中由于挥发物的释放而产生的缺陷。
• Samarium diiodide/nickel diiodide an efficient system for homo and heterocoupling reactions of imines
  作者：Fouzia Machrouhi、Jean-Louis Namy

  DOI：10.1016/s0040-4039(98)02673-2

  日期：1999.2

  Samarium diiodide in the presence of a catalytic amount of nickel diiodide mediates a very fast dimerization of imines into vicinal diamines and the mixed coupling of imines and ketones to give β-amino alcohols.

  在催化量的二碘化镍存在下，二碘化可将亚胺非常快速地二聚为邻位二胺，并将亚胺和酮混合偶联，生成β-氨基醇。
• Catalytic imino Diels–Alder reaction by triflic imide and its application to one-pot synthesis from three components
  作者：Kiyosei Takasu、Naoya Shindoh、Hidetoshi Tokuyama、Masataka Ihara

  DOI：10.1016/j.tet.2006.09.092

  日期：2006.12

  An imino Diels–Alder reaction of 2-siloxydienes with aldimines catalyzed by triflic imide (Tf2NH; 0.1∼10 mol % amount) has been developed leading to substituted piperidin-4-ones. Tf2NH catalyst is compatible with basic functions, such as pyridine and indole rings in the imino Diels–Alder reaction. Furthermore, X-ray crystallographic analysis indicates that trans-2,6-diphenyl-4-piperidinone 4a obtained

  已经开发了2-甲硅烷基二烯与三氟甲酰亚胺（Tf 2 NH； 0.1〜10 mol％的量）催化的醛亚胺的亚氨基Diels-Alder反应，从而产生了取代的哌啶-4-酮。Tf 2 NH催化剂与基本功能兼容，例如亚氨基Diels-Alder反应中的吡啶和吲哚环。此外，X射线晶体学分析表明，通过该反应获得的反式-2,6-二苯基-4-哌啶酮4a在固态具有独特的构象。