2-(2-methoxyphenyl)-1-phenylethan-1-amine | 704200-89-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(2-methoxyphenyl)-1-phenylethan-1-amine
• 英文别名: 2'-methoxy-bibenzyl-α-ylamine；2'-Methoxy-bibenzyl-α-ylamin；α'-Amino-2-methoxy-bibenzyl；2-(2-Methoxyphenyl)-1-phenylethanamine
• CAS: 704200-89-5
• 化学式: C₁₅H₁₇NO
• mdl: MFCD09887662
• 分子量: 227.306
• InChiKey: XNLHJPFLVKFDHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-methoxyphenyl)-1-phenylethan-1-amine 、 邻氯乙苯 在 乙醇 、 sodium carbonate 作用下， 生成 (2-methoxy-bibenzyl-α-yl)-phenethyl-amine
  参考文献：
  名称：

  DE617647

  摘要：

  公开号：
• 作为产物：
  描述：

  α'-Nitro-2-methoxy-stilben 在 甲醇 、 钯 作用下， 生成 2-(2-methoxyphenyl)-1-phenylethan-1-amine
  参考文献：
  名称：

  The Catalytic Reduction of α-Nitrostilbenes to α, β-Diphenylethylamines

  摘要：

  DOI：

  10.1021/ja01213a507

文献信息

• Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite
  作者：Atsushi Kaga、Hirohito Hayashi、Hiroyuki Hakamata、Miku Oi、Masanobu Uchiyama、Ryo Takita、Shunsuke Chiba

  DOI：10.1002/anie.201705916

  日期：2017.9.18

  Come full circle: A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.

  围成一圈：在碘化锂（LiI）存在下，使用氢化钠（NaH）建立了甲氧基芳烃的亲核胺化方法。该方法提供了一条有效的途径来制得二环氮杂环。机理研究表明，该反应通过异常的协同的亲核芳族取代进行。
• Alkaline-Metal-Catalyzed One-Pot Aminobenzylation of Aldehydes with Toluenes
  作者：Guoqing Liu、Patrick J. Walsh、Jianyou Mao

  DOI：10.1021/acs.orglett.9b02737

  日期：2019.11.1

  A novel and easily accessible MN(SiMe3)2 (M = Li or Na)/Cs2CO3 co-catalyzed benzylation of in situ generated N-(trimethylsilyl) aldimines with toluene derivatives has been successfully developed. The catalyst exhibits high chemoselectivity for deprotonation of toluenes at the benzylic position. The utility of this system is exemplified by the one-pot synthesis of a diverse array of bioactive 1,2-diarylethylamines

  已成功开发了一种新颖且易于使用的MN（SiMe 3）2（M = Li或Na）/ Cs 2 CO 3催化原位生成的N-（三甲基甲硅烷基）亚胺与甲苯衍生物的苄基化反应。该催化剂对苄基位置的甲苯去质子表现出高化学选择性。一锅合成具有优异效率和宽泛的官能团耐受性的各种生物活性1,2-二芳基乙胺的例子说明了该系统的实用性。
• Regiochemistry on photoamination of stilbene derivatives with ammonia via electron transfer
  作者：Masahide Yasuda、Toshihiro Isami、Junichi Kubo、Manabu Mizutani、Toshiaki Yamashita、Kensuke Shima

  DOI：10.1021/jo00031a010

  日期：1992.2

  The regiochemistry of photoamination of 1,2-diarylethene (1) with ammonia in the presence of p-dicyanobenzene (DCNB) has been investigated. The photoamination of stilbene and p,p'-dimethoxystilbene gave 1-amino-1,2-diphenylethane and 1-amino-1,2-bis(p-methoxyphenyl)ethane, respectively. The photoamination of unsymmetric 1-aryl-2-phenylethene having an alkoxy group on the para position occurred selectively to give 1-amino-2-aryl-1-phenylethane. On the other hand, the photoamination of 1-aryl-2-phenylethene having a methyl and chloro group on the para position or methoxy group on the meta and ortho positions gave both 1-amino-2-aryl-1-phenylethane and 1-amino-1-aryl-2-phenylethane. The regiochemistry is related with the distribution of positive charge in the cation radicals of 1 generated from photochemical electron transfer to DCNB.
• AN IMPROVED ASYMMETRIC SYNTHESIS OF alpha-BRANCHED CHIRAL AMINES
  申请人：PIRAMAL PHARMA LIMITED

  公开号：US20210114977A1

  公开（公告）日：2021-04-22

  The present invention relates to an improved asymmetric synthesis of alpha-branched amines (hereafter referred to as the compound) and relative chiral amines (1″) or its pharmaceutically acceptable salt and derivatives. The process comprises an unusual substrate specific regioselective ortho lithiation of substituted arene compounds, followed by its highly diastereoselective addition to N-tert-butanesulfinylimines resulting in the selective formation of alpha-branched sulfinyl amine and chiral amine; which on subsequently removing the sulfinyl group provides corresponding alpha-branched amines or relative chiral amines (1″).