1-(3-methoxyphenyl)-N-methylethan-1-imine | 118761-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-methoxyphenyl)-N-methylethan-1-imine
• 英文别名: 1-(3-methoxyphenyl)-N-methylethanimine
• CAS: 118761-92-5
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: IVHWLMCMIRTABS-UHFFFAOYSA-N

物化性质

• 沸点：
  234.6±32.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-methoxyphenyl)-N-methylethan-1-imine 在 lithium aluminium tetrahydride 、 (S)-3,3'-bis[4-methyl-3,5-dinitrophenyl]-1,1'-binaphthyl-2,2'-disulfonimide 、 氢溴酸 、 2,6-二甲基-1,4-二氢吡啶-3,5-二甲酸二叔丁酯 作用下， 以 乙醚 、 水 、 均三甲苯 为溶剂， 反应 124.0h， 生成 3-(1-(S)-(N,N-二甲基氨基)乙基)苯酚
  参考文献：
  名称：

  二磺酰亚胺催化的N-烷基亚胺的不对称还原

  摘要：

  在Boc 2 O存在的情况下，已开发出一种以Hantzsch酯为氢源的手性二磺酰亚胺（DSI）催化N烷基亚胺的不对称还原。该反应可提供具有出色收率和对映选择性的Boc保护的N-烷基胺。该方法可耐受多种烷基胺，从而说明了酮与各种胺的一般还原性交叉偶联的潜力，并已用于药物（S）-利伐斯的明，NPS R-568盐酸盐的合成，以及（R）-芬迪林。

  DOI：

  10.1002/anie.201504052
• 作为产物：
  描述：

  N-chloro-1-(3-methoxyphenyl)-N-methylethan-1-amine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1-(3-methoxyphenyl)-N-methylethan-1-imine
  参考文献：
  名称：

  Reactions of N-halo-N-methylbenzylamines with sodium methoxide-methanol and potassium tert-butoxide-tert-butyl alcohol. Effects of .beta.-carbon substituent and base-solvent system upon the imine-forming transition state

  摘要：

  DOI：

  10.1021/ja00188a046

文献信息

• Iron catalysed nitrosation of olefins to oximes
  作者：Ritwika Ray、Abhishek Dutta Chowdhury、Debabrata Maiti、Goutam Kumar Lahiri

  DOI：10.1039/c3dt51764k

  日期：——

  Fe(BF4)2·6H2O/2,6-pyridinedicarboxylic acid catalysed nitrosation of a wide variety of substituted styrenes has been developed in the presence of t-BuONO/NaBH4 under H2 pressure (10 bar) in MeOH–H2O (5 : 1) to afford corresponding oximes in good to excellent yields.

  在Fe(BF4)2·6H2O/2,6-吡啶二羧酸的催化下，通过在H2压力（10巴）、t-BuONO/NaBH4存在下，以MeOH-H2O（5:1）为溶剂，广泛研究了各种取代苯乙烯的亚硝化反应，得到了相应的肟类化合物，产率良好至优异。
• Direct Asymmetric Hydrogenation of <i>N</i>-Methyl and <i>N</i>-Alkyl Imines with an Ir(III)H Catalyst
  作者：Ernest Salomó、Albert Gallen、Giuseppe Sciortino、Gregori Ujaque、Arnald Grabulosa、Agustí Lledós、Antoni Riera、Xavier Verdaguer

  DOI：10.1021/jacs.8b11547

  日期：2018.12.12

  A novel cationic [IrH(THF)(P,N)(imine)] [BArF] catalyst containing a P-stereogenic MaxPHOX ligand is described for the direct asymmetric hydrogenation of N-methyl and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile tetrahydrofuran ligand allows for effective activation and reactivity, even at low temperatures

  描述了一种新型阳离子 [IrH(THF)(P,N)(亚胺)] [BArF] 催化剂，该催化剂含有 P-立体异构 MaxPHOX 配体，用于 N-甲基和 N-烷基亚胺的直接不对称氢化。这是第一个在此类转化中实现高对映选择性（高达 94% ee）的催化系统。即使在低温下，不稳定的四氢呋喃配体也能实现有效的活化和反应。密度泛函理论计算使得反应的立体化学过程合理化。
• Cyclometallated Imides as Templates for the H‐Bond Directed Iridium‐Catalyzed Asymmetric Hydrogenation of N‐Methyl, N‐Alkyl and N‐Aryl Imines
  作者：Yisong Wen、Marc Fernández-Sabaté、Agustí Lledós、Giuseppe Sciortino、James Eills、Irene Marco-Rius、Antoni Riera、Xavier Verdaguer

  DOI：10.1002/anie.202404955

  日期：——

  A combined computational and experimental approach allowed us to develop the most selective catalysts for the direct hydrogenation of N‐methyl and N‐alkyl imines described to date. Iridium catalysts with a cyclometallated cyclic imide group provide selectivity of up to 99% enantiomeric excess. Computational studies show that the selectivity results from the combined effect of H‐bonding of the imide C=O with the substrate iminium ion and a stabilizing π‐π interaction with the cyclometallated ligand. The cyclometallated ligand thus exhibits a unique mode of action, serving as a template for the H‐bond directed approach of the substrate which results in enhanced selectivity. The catalyst (2) has been synthesized and isolated as a crystalline air‐stable solid. X‐ray analysis of 2 confirmed the structure of the catalyst and the correct position of the imide C=O groups to engage in an H‐bond with the substrate. 19F‐NMR real‐time monitoring showed the hydrogenation of N‐methyl imines catalyzed by 2 is very fast, with a TOF of approx. 3500 h‐1.
• 10.1039/d4ob00896k
  作者：Xie, Jia-Qi、Wang, Bing-Xia、Liang, Ren-Xiao、Jia, Yi-Xia

  DOI：10.1039/d4ob00896k

  日期：——
• Disulfonimide‐Catalyzed Asymmetric Reduction of <i>N</i> ‐Alkyl Imines
  作者：Vijay N. Wakchaure、Philip S. J. Kaib、Markus Leutzsch、Benjamin List

  DOI：10.1002/anie.201504052

  日期：2015.9.28

  A chiral disulfonimide (DSI)‐catalyzed asymmetric reduction of N‐alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O has been developed. The reaction delivers Boc‐protected N‐alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross‐coupling of ketones with diverse

  在Boc 2 O存在的情况下，已开发出一种以Hantzsch酯为氢源的手性二磺酰亚胺（DSI）催化N烷基亚胺的不对称还原。该反应可提供具有出色收率和对映选择性的Boc保护的N-烷基胺。该方法可耐受多种烷基胺，从而说明了酮与各种胺的一般还原性交叉偶联的潜力，并已用于药物（S）-利伐斯的明，NPS R-568盐酸盐的合成，以及（R）-芬迪林。