4-chloro-N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpyridine-2-carboxamide | 1158179-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-chloro-N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpyridine-2-carboxamide
• CAS: 1158179-41-9
• 化学式: C₁₆H₁₇ClN₂O₂
• 分子量: 304.776
• InChiKey: PRAVHNQUJNFCMQ-NHYWBVRUSA-N

物化性质

• 熔点：
  139-141 °C
• 沸点：
  507.5±50.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-吡啶-2-酰氯 、 麻黄碱 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以71%的产率得到4-chloro-N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpyridine-2-carboxamide
  参考文献：
  名称：

  Highly Stereoselective Metal-Free Catalytic Reduction of Imines: An Easy Entry to Enantiomerically Pure Amines and Natural and Unnatural α-Amino Esters

  摘要：

  A highly efficient catalytic stereoselective ketimine reduction is described. The combination of an inexpensive chiral organocatalyst, easily prepared in a single step, and of a very cheap removable chiral auxiliary allowed us to obtain enantiomerically pure amino compounds. The methodology allowed synthesis of chiral secondary and primary amines and natural and unnatural amino esters in high yields often with total control of the absolute stereochemistry.

  DOI：

  10.1021/ol900945h
• 作为试剂：
  描述：

  2,2,2,4'-四氟苯乙酮 、 甲氧苯胺 在 4-chloro-N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpyridine-2-carboxamide 、 三氯硅烷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.5h， 生成 (S)-4-methoxy-N-(2,2,2-trifluoro-1-(4-fluorophenyl)ethyl)aniline 、 N-(4-methoxyphenyl)-2,2,2-trifluoro-1-(4-fluorophenyl)ethan-1-amine
  参考文献：
  名称：

  手性三氟甲基芳基和烷基胺的立体选择性无金属催化合成。

  摘要：

  三氟甲基芳基和烷基酮亚胺的对映选择性有机催化还原提供了具有高化学和立体化学效率的相应氟化胺。Lewis碱与三氯硅烷的催化反应生成具有三氟甲基的手性产物，该三氟甲基直接与新生成的立体中心相连，产率通常> 90％，ee最高可达98％

  DOI：

  10.1039/c3cc43821j

文献信息

• Chiral Lewis base promoted trichlorosilane reduction of ketimines. An enantioselective organocatalytic synthesis of chiral amines
  作者：Stefania Guizzetti、Maurizio Benaglia、Franco Cozzi、Rita Annunziata

  DOI：10.1016/j.tet.2009.06.015

  日期：2009.8

  The reduction of the carbon-nitrogen double bond is an important transformation. Here we report our studies on a family of chiral organic catalysts able to promote the stereoselective reduction of ketimines with trichlorosilane. The very cheap, metal-free catalysts were easily prepared in one step from commercially available products, namely a chiral aminoalcohol and picolinic acid derivatives. The catalyst structure was extensively modified in a study that allowed to identify an extremely active species, able to promote the reduction on a large variety of substrates with high efficiency (up to 95% ee). A three component methodology has been also developed, where the enantiomerically enriched amine was isolated after performing the reaction by mixing a ketone and an amine in the presence of trichlorosilane and the catalyst. Its synthetic potentiality was demonstrated by employing the present metal-free catalytic procedure in the preparation of (S)-metolachlor, a potent and widely used herbicide. (C) 2009 Elsevier Ltd. All rights reserved.
• Highly Stereoselective Metal-Free Catalytic Reduction of Imines: An Easy Entry to Enantiomerically Pure Amines and Natural and Unnatural α-Amino Esters
  作者：Stefania Guizzetti、Maurizio Benaglia、Sergio Rossi

  DOI：10.1021/ol900945h

  日期：2009.7.2

  A highly efficient catalytic stereoselective ketimine reduction is described. The combination of an inexpensive chiral organocatalyst, easily prepared in a single step, and of a very cheap removable chiral auxiliary allowed us to obtain enantiomerically pure amino compounds. The methodology allowed synthesis of chiral secondary and primary amines and natural and unnatural amino esters in high yields often with total control of the absolute stereochemistry.