1-phenyl-N-(2-phenylethyl)methanimine | 3240-95-7

• 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: 1-phenyl-N-(2-phenylethyl)methanimine
• 英文别名: (E)-N-(phenylethyl)-1-phenylmethanimine；(E)-N-benzylidene-2-phenylethanamine；(E)-N-phenethyl-1-phenylmethanimine；N-benzylidenebenzeneethanamine；benzylidene-phenethyl-amine
• CAS: 3240-95-7
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: OOBAKFDIGIHHOM-DTQAZKPQSA-N

物化性质

• 熔点：
  33-34 °C
• 沸点：
  118-120 °C(Press: 0.03 Torr)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  1-phenyl-N-(2-phenylethyl)methanimine 在 三氟甲磺酸 作用下， 反应 15.0h， 以90%的产率得到1-苯基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Prototype Pictet−Spengler Reactions Catalyzed by Superacids. Involvement of Dicationic Superelectrophiles

  摘要：

  The Pictet-Spengler reaction, an acid-catalyzed intramolecular cyclization of intermediate imines of 2-arylethylamine to give 1,2,3,4-tetrahydroisoquinolines, has long been limited to active substrates which bear strongly electron-donating groups such as a methoxy or a hydroxy group on the cyclizing benzene ring. in this paper, we present superacid-catalyzed Pictet-Spengler reactions of imines of a-phenethylamine, including the prototype Pictet-Spengler reaction of N-methylene-2-phenethylamine, to give the parent and 1-substituted 1,2,3,4-tetrahydroisoquinolines in moderate to high yields. The yields are dependent on the acidity of the media. A linear relationship was found between the rate of the cyclization and the acidity of the reaction media in kinetic studies of N-methylene-2-phenethylamine and related imines, strongly supporting the intervention of an additional protonative activation of the N-protonated imines, that is, the involvement of dicationic superelectrophiles, N,N-diprotonated imines (ammonium-carbenium dications). We further found that the prototype cyclization of the parent N-methylene-2-phenethylamine is also catalyzed by TFA to give 1,2,3,4-tetrahydroisoquinoline in good yield, although the cyclization is significantly slower than that catalyzed by superacids. The prototype Pictet-Spengler cyclization of N-methylene-2-phenethylamine can thus take place both through the monocation (the N-monoprotonated imine) and the dication (the N,N-diprotonated imine), the latter reaction being predominant in superacids.

  DOI：

  10.1021/jo982019e
• 作为产物：
  描述：

  N-苄基-2-苯乙酰胺 在 叔丁基过氧化氢 、 calcined ZnCrCO₃-HTlc 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以90%的产率得到1-phenyl-N-(2-phenylethyl)methanimine
  参考文献：
  名称：

  Calcined ZnCrCo₃-HTlc for the oxidation of benzyl amines to schiff bases⁺

  摘要：

  Oxidation of benzylamines to Schiff bases has been carried out using a mixed oxide catalyst obtained by the calcination of ZnCrCO3-HTlc which is a member of the anionic clay family.

  DOI：

  10.1080/00397919608086735

文献信息

• Molecular Sieves in Ionic Liquids as an Efficient and Recyclable Medium for the Synthesis of Imines
  作者：Carlos Kleber Andrade、Paulo Anselmo Suarez、Sayuri Cristina Takada、Luana Magalhães Alves、Juliana Petrocchi Rodrigues、Rodrigo Fleury Brandão、Valério Cassiano Soares

  DOI：10.1055/s-2004-831328

  日期：——

  A great variety of imines were efficiently isolated in high yields from the reaction of aldehydes and amines in ionic liquids. The ionic liquids could be recovered and reused for at least five cycles without loss in the yields being a useful alternative to dichloromethane or diethyl ether, which are the commonly used solvents for this reaction.

  多种亚胺得以高效地从醛和胺在离子液体中的反应中高产率地分离出来。这些离子液体可被回收并在至少五个循环中重复使用，而产率无明显下降，这为常用的反应溶剂二氯甲烷或乙醚提供了一个有用的替代选择。
• Aerobic Oxidation of Primary Amines to Imines in Water using a Cobalt Complex as Recyclable Catalyst under Mild Conditions
  作者：Susanta Hazra、Priti Pilania、Mayukh Deb、Ajay Kishor Kushawaha、Anil J. Elias

  DOI：10.1002/chem.201803251

  日期：2018.10.22

  Oxidative coupling of primary amines to imines has been achieved by using a water soluble cobalt complex as catalyst and air as the oxidant at near ambient conditions. Aromatic, heteroaromatic and aliphatic amines were successfully converted to the corresponding imines with yields of up to 96 %. A 20 gram scale reaction for the synthesis of imine from benzylamine in good yield is also demonstrated

  伯胺与亚胺的氧化偶联已通过在近乎环境条件下使用水溶性钴配合物作为催化剂并使用空气作为氧化剂来实现。芳香族，杂芳香族和脂肪族胺已成功转化为相应的亚胺，产率高达96％。用该方法还证明了20克规模的反应，用于从苄胺以高收率合成亚胺。已经发现该催化剂可重复使用多达五个循环。它高效，周转率（TON）高达128，并显示化学选择性，唯一的副产物是水和氨。对照实验和机理研究表明，Co II / Co III催化循环负责这些氧化转化。该反应的一些反应性中间体也已经被分离和结构表征。
• [EN] MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS<br/>[FR] COMPLEXES À BASE DE MANGANÈSE ET LEURS UTILISATIONS SERVANT À UNE CATALYSE HOMOGÈNE
  申请人：YEDA RES & DEV

  公开号：WO2017137984A1

  公开（公告）日：2017-08-17

  The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.

  本发明涉及新型锰配合物及其用途，包括但不限于在以下领域进行均相催化：（1）通过醇和胺的脱氢偶联制备亚胺；（2）使用腈作为迈克尔供体进行迈克尔加成反应中的C-C偶联；（3）将醇脱氢偶联以得到酯和氢气；（4）将酯加氢以形成醇（包括环酯（内酯）或环二酯（二内酯）或聚酯的加氢）；（5）将酰胺（包括环二肽、内酰胺、二酰胺、多肽和聚酰胺）加氢以得到醇和胺（或二胺）；（6）将有机碳酸酯（包括聚碳酸酯）加氢以得到醇或将氨基甲酸酯（包括聚氨基甲酸酯）或脲衍生物加氢以得到醇和胺；（7）将二级醇脱氢以得到酮；（8）酯的酰胺化（即从酯和胺合成酰胺）；（9）使用酯对醇进行酰化；（10）将醇与水和碱偶联以形成羧酸；以及（11）通过氨基醇与水和碱的偶联制备氨基酸或其盐。（12）通过醇和胺的脱氢偶联制备酰胺（包括甲酰胺、环二肽、二酰胺、内酰胺、多肽和聚酰胺）；（13）从二醇制备酰亚胺。
• Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
  作者：Xinyun Liu、Johnny H Phan、Benjamin J Haugeberg、Shrikant S Londhe、Michael D Clift

  DOI：10.3762/bjoc.13.282

  日期：——

  A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative

  报道了一种通过醌催化的1,2-氨基醇氧化甲酰化合成亚胺的新方法。各种容易获得的氨基醇和伯胺都可以反应生成N保护的亚胺产品。提出的方法为亚胺合成提供了一种新颖的有机催化方法，并证明了醌催化的氧化CC键裂解的合成多功能性。
• New Modification of the Intramolecular α-Amidoalkylation for the Synthesis of 2-Acyl-1,2,3,4-tetrahydroisoquinolines
  作者：Atanas P. Venkov、Ludmil K. Lukanov

  DOI：10.1055/s-1989-27153

  日期：——

  2-Acyl-1,2,3,4-tetrahydroisoquinolines are obtained from N-methylene- or N-benzylidene-2-phenylethylamines and acyl chlorides or carboxylic acids/thionyl chloride in the presence of potassium iodide at room temperature.

  室温下，在碘化钾存在时，N-亚甲基或N-苄叉基-2-苯乙胺与酰氯或羧酸/亚硫酰氯反应，可以得到2-酰基-1,2,3,4-四氢异喹啉。

表征谱图