1-(2-methoxyphenyl)-N-[(1S)-1-phenylethyl]ethanimine | 95447-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-methoxyphenyl)-N-[(1S)-1-phenylethyl]ethanimine
• CAS: 95447-94-2
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: VGZHFCYNXIFZHS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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-(2-methoxyphenyl)-N-[(1S)-1-phenylethyl]ethanimine 在 氢气 作用下， 以 醋酸异丙酯 为溶剂， 24.0 ℃ 、1.0 MPa 条件下， 反应 16.0h， 生成 N-<1(S)-(2-methoxyphenyl)ethyl>-1-(S)-phenylethylamine
  参考文献：
  名称：

  顺序还原胺化-氢解：具有挑战性的手性伯胺的一锅合成

  摘要：

  以良好至高产率并且形成难以访问手性伯胺EE使用一锅合成从前手性酮的一个罕见的例子（顺序还原性胺化-hydrogenloysis）。作为亮点，我们还证明了邻甲氧基苯乙酮的一锅还原胺化-氢解还原还原胺化（五个反应）产生了手性二胺1-（2-甲氧基苯基）乙基-（2-吡啶基甲基）-胺（4）（ 58％的总收率，> 99％ee），这是一种用于水性对映选择性羟醛反应的新型有机催化剂。

  DOI：

  10.1002/adsc.201100250
• 作为产物：
  描述：

  [1-(2-Methoxy-phenyl)-eth-(E)-ylidene]-(1-phenyl-ethyl)-amine 生成 1-(2-methoxyphenyl)-N-[(1S)-1-phenylethyl]ethanimine
  参考文献：
  名称：

  Diastereoselective hydrogenation and kinetic resolution of imines using rhodium/diphosphine catalyzed hydrogenation.

  摘要：

  Kinetic resolution of racemic alpha-methylbenzyl amine can be achieved with 98% e.e. of the remaining amine at 70% conversion using the Rhodium/2S,4S-BDPP catalyzed asymmetric hydrogenation of imines. The same catalyst will hydrogenate optically pure alpha-methylbenzyl amines with a diastereoselectivity of up to 333:1.

  DOI：

  10.1016/s0957-4166(00)82341-1

文献信息

• Step-Efficient Access to Chiral Primary Amines
  作者：Thomas Nugent、Sofiya Marinova

  DOI：10.1055/s-0032-1317589

  日期：——

  Routes to enantioenriched amines are outlined that employ reductive amination and carbanion addition methods. The strategies require either one or two reaction steps from prochiral carbonyl compounds for the synthesis of the corresponding chiral primary amines.
• Highly Diastereoselective Hydrogenation of Imines by a Bimetallic Pd−Cu Heterogeneous Catalyst
  作者：Jale Müslehiddinoğlu、Jun Li、Srinivas Tummala、Rajendra Deshpande

  DOI：10.1021/op1001325

  日期：2010.7.16

  An efficient and practical heterogeneous bimetallic Pd-Cu/C catalyst was identified as an alternative to Raney nickel for the highly diastereoselective hydrogenation of imines prepared from prochiral ketones and alpha-phenylethylamines. Chiral amines were obtained with diastereomeric excess (de) up to 94% using Pd-Cu/C, while conventional Pd-C catalysts afforded only 72% de. Optimization showed that a robust process required a palladium/copper ratio of 4:1. Evidence for the influence of catalyst pretreatment which may change the structure of the catalyst and/or metal oxidation states on the selectivity of the reaction is discussed. The bimetallic catalyst system provided consistent results on scale and performed reliably on a variety of substrates.
• Diastereoselective synthesis of chiral secondary amines with two chiral centers directly attached to the nitrogen atom
  作者：M. B. Eleveld、H. Hogeveen、E. P. Schudde

  DOI：10.1021/jo00369a016

  日期：1986.9
• Sequential Reductive Amination-Hydrogenolysis: A One-Pot Synthesis of Challenging Chiral Primary Amines
  作者：Thomas C. Nugent、Daniela E. Negru、Mohamed El-Shazly、Dan Hu、Abdul Sadiq、Ahtaram Bibi、M. Naveed Umar

  DOI：10.1002/adsc.201100250

  日期：2011.8

  Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethy

  以良好至高产率并且形成难以访问手性伯胺EE使用一锅合成从前手性酮的一个罕见的例子（顺序还原性胺化-hydrogenloysis）。作为亮点，我们还证明了邻甲氧基苯乙酮的一锅还原胺化-氢解还原还原胺化（五个反应）产生了手性二胺1-（2-甲氧基苯基）乙基-（2-吡啶基甲基）-胺（4）（ 58％的总收率，> 99％ee），这是一种用于水性对映选择性羟醛反应的新型有机催化剂。
• Diastereoselective hydrogenation and kinetic resolution of imines using rhodium/diphosphine catalyzed hydrogenation.
  作者：Cornelis Lensink、Johannes G. de Vries

  DOI：10.1016/s0957-4166(00)82341-1

  日期：1993.2

  Kinetic resolution of racemic alpha-methylbenzyl amine can be achieved with 98% e.e. of the remaining amine at 70% conversion using the Rhodium/2S,4S-BDPP catalyzed asymmetric hydrogenation of imines. The same catalyst will hydrogenate optically pure alpha-methylbenzyl amines with a diastereoselectivity of up to 333:1.