1-(4-Methoxy-phenyl)-N-phenyl-propyl-amin | 22920-60-1

• 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-(4-Methoxy-phenyl)-N-phenyl-propyl-amin
• 英文别名: N-[1-(4-methoxyphenyl)propyl]aniline
• CAS: 22920-60-1
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: GDWAOJMKYYJLPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲氧基苯丙酮 在 (2S)-1-formyl-N-Ph-piperazine-2-carboxamide-based reagent 、 4 A molecular sieve 、 三氯硅烷 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 60.0h， 生成 1-(4-Methoxy-phenyl)-N-phenyl-propyl-amin
  参考文献：
  名称：

  1-哌嗪-2-羧酸衍生的N-甲酰胺，是一种高度对映选择性的路易斯碱性催化剂，用于N-芳基亚胺的氢化硅烷化，具有前所未有的底物特性。

  摘要：

  [反应：见正文] 1-哌嗪-2-羧酸衍生的N-甲酰胺已被开发为高度对映选择性的Lewis碱性催化剂，用于N-芳基亚胺与三氯硅烷的氢化硅烷化反应。发现N 4上的芳烃磺酰基对于催化剂的高对映选择性是至关重要的。对于包括芳香族和脂肪族酮亚胺在内的多种底物，特别是那些具有相对较大烷基的R（2）的底物，均获得了高分离产率（高达99％）和对映选择性（高达97％）。

  DOI：

  10.1021/ol060984i

文献信息

• Development of highly enantioselective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile
  作者：Pengcheng Wu、Zhouyu Wang、Mounuo Cheng、Li Zhou、Jian Sun

  DOI：10.1016/j.tet.2008.09.034

  日期：2008.12

  ketimines and non-methyl ketimines were catalyzed to afford the desired amines in good to high yield and enantioselectivity. In particular, catalyst 6e enabled the reduction of the difficult bulky ketimines to be highly efficient and enantioselective, affording up to 99% yield and 97% ee. This catalyst proved to prefer the relatively bulkier non-methyl acyclic ketimines to the methyl ketimines as substrate

  已经开发了由1-哌啉酸衍生的N-甲酰胺作为新的路易斯碱性有机催化剂，其使用三氯硅烷作为还原剂来促进N-芳基酮亚胺的不对称还原。哌嗪基主链的N 4上的取代基和2-羧酰胺基均被证明对催化剂的功效具有深远的影响。催化N-芳基无环甲基酮亚胺和非甲基酮亚胺的还原，以高至高收率和对映选择性提供所需的胺。特别是催化剂6e使难于分离的笨重的酮亚胺高效且对映选择性降低，可提供高达99％的收率和97％的ee。事实证明，该催化剂比甲基酮亚胺更优选相对较大的非甲基非环酮亚胺作为底物，这在亚胺的催化不对称还原方面是前所未有的。
• Regioselective Preparation of 2-Phenylethylamines from 1-Phenyl-2-alkyl­alkynes by Hydroamination/Reduction Sequences
  作者：Sven Doye、Andreas Heutling、René Severin

  DOI：10.1055/s-2004-834863

  日期：——

  Ind2TiMe2 is a highly active and general catalyst for the intermolecular hydroamination of alkynes. Particularly impressive is that Ind2TiMe2 makes it possible to perform hydroamination reactions of unsymmetrically substituted 1-phenyl-2-alkylalkynes with primary aryl-, tert-alkyl-, sec-alkyl-, and n-alkylamines in a highly regioselective fashion. Since the initially formed imines can easily be reduced with zinc-modified NaBH3CN, 2-phenylethylamines are accessible in reliable one-pot procedures from 1-phenyl-2-alkylalkynes and primary amines on a 10 mmol scale.

  Ind2TiMe2 是炔烃分子间氢化反应的高活性通用催化剂。尤其令人印象深刻的是，Ind2TiMe2 能够以高度区域选择性的方式使不对称取代的 1-苯基-2-烷基炔与伯芳基、叔烷基、仲烷基和正烷基胺发生氢化反应。由于最初形成的亚胺可以很容易地用锌改性的 NaBH3CN 还原，因此可以在 10 毫摩尔的规模上通过可靠的一锅法从 1-苯基-2-烷基炔和伯胺中获得 2-苯基乙胺。
• Iron-catalyzed intermolecular 1,2-difunctionalization of alkenes with nucleophiles and using di-tert-butyl peroxide as the methylation reagent
  作者：Fengxiang Zhu、Jianxin Xue、Xiao-Feng Wu

  DOI：10.1016/j.tet.2023.133735

  日期：2023.12

  di-tert-butyl peroxide as the methylation reagent has been reported. Employing FeSO4 as the catalyst allows various of alkenes 1,2-methylamination, and 1,2-methylarylation, which rely on a wide spectrum of nucleophiles, such as aromatic amines, pyrrole, and indoles. This protocol is characterized by its simplicity which allowing the rapid building of complex molecules from simple starting materials.

  据报道，以二叔丁基过氧化物为甲基化试剂，Fe(II) 催化的烯烃三组分 1,2-双官能化反应。使用FeSO 4作为催化剂可以实现各种烯烃的1,2-甲基胺化和1,2-甲基芳基化，这依赖于广泛的亲核试剂，例如芳香胺、吡咯和吲哚。该方案的特点是其简单性，允许从简单的起始材料快速构建复杂的分子。
• Addition of diethylzinc to imines promoted by Lewis acid
  作者：Xue Long Hou、Xiao Lan Zheng、Li Xin Dai

  DOI：10.1016/s0040-4039(98)01442-7

  日期：1998.9

  The alkylation of imines by using diethylzinc reagent in the presence of Lewis acid afforded secondary amines in high yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• <scp>l</scp>-Piperazine-2-carboxylic Acid Derived <i>N</i>-Formamide as a Highly Enantioselective Lewis Basic Catalyst for Hydrosilylation of <i>N</i>-Aryl Imines with an Unprecedented Substrate Profile
  作者：Zhouyu Wang、Mounuo Cheng、Pengcheng Wu、Siyu Wei、Jian Sun

  DOI：10.1021/ol060984i

  日期：2006.7.1

  l-Piperazine-2-carboxylic acid derived N-formamides have been developed as highly enantioselective Lewis basic catalysts for the hydrosilylation of N-aryl imines with trichlorosilane. The arene sulfonyl group on N4 was found to be critical for the high enantioselectivity of the catalyst. High isolated yields (up to 99%) and enantioselectivities (up to 97%) were obtained for a broad range of substrates, including

  [反应：见正文] 1-哌嗪-2-羧酸衍生的N-甲酰胺已被开发为高度对映选择性的Lewis碱性催化剂，用于N-芳基亚胺与三氯硅烷的氢化硅烷化反应。发现N 4上的芳烃磺酰基对于催化剂的高对映选择性是至关重要的。对于包括芳香族和脂肪族酮亚胺在内的多种底物，特别是那些具有相对较大烷基的R（2）的底物，均获得了高分离产率（高达99％）和对映选择性（高达97％）。