(1R,2S)-N-picolinoyl ephedrine | 960009-42-1

• 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: (1R,2S)-N-picolinoyl ephedrine
• 英文别名: N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpyridine-2-carboxamide
• CAS: 960009-42-1
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: NUYOSZVUBKDFIO-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 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

• 作为反应物：
  描述：

  (1R,2S)-N-picolinoyl ephedrine 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以29%的产率得到N-((1R,2S)-1-methoxy-1-phenylpropan-2-yl)-N-methylpicolinamide
  参考文献：
  名称：

  Chiral Lewis base promoted trichlorosilane reduction of ketimines. An enantioselective organocatalytic synthesis of chiral amines

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.06.015
• 作为产物：
  描述：

  2-吡啶甲酸 、 麻黄碱 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 24.25h， 以70%的产率得到(1R,2S)-N-picolinoyl ephedrine
  参考文献：
  名称：

  Chiral organic catalysts for the stereoselective reduction of carbon-nitrogen double bonds for the preparation of enantiomerically enriched amines

  摘要：

  本发明涉及一般式(I)的化合物：其中R1-R7如描述中定义，用作催化剂，存在三氯硅烷还原剂的情况下进行亚胺的立体选择性还原。

  公开号：

  EP2065371A1
• 作为试剂：
  描述：

  4,4,4-三氟-2-丁炔乙酯 在 (1R,2S)-N-picolinoyl ephedrine 、 三氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 18.17h， 生成
  参考文献：
  名称：

  对立体选择性合成 Retro-Thiorphan 的氟化类似物的批量和流入合成策略的评价

  摘要：

  已经分批研究了一种立体选择性合成策略，用于制备三氟甲胺模拟物的三氟甲胺模拟物，涉及非对映选择性、无金属催化步骤，并以良好的收率和高非对映选择性提供目标分子。合成顺序的一个关键点是在手性路易斯碱的存在下用三氯硅烷作为还原剂催化还原氟化烯胺。通过 X 射线分析明确指定了关键中间体的绝对构型。还研究了利用连续流动反应的合成；也就是说，目标分子的高级中间体仅在两个流入合成模块中合成，避免了中间体的分离和纯化，

  DOI：

  10.3390/molecules24122260

文献信息

• NOVEL PICOLINAMIDE-CINCHONA ORGANOCATALYSTS AND DERIVATIVES
  申请人：UNIVERSIDADE DE ÉVORA

  公开号：US20160236184A1

  公开（公告）日：2016-08-18

  The present application describes a novel type of picolinamide-cinchona organocatalyst that allows for the successful transformation of ketimines to chiral amines with very high enantioselectivities and with the highest TOFs reported for any particular organocatalyst to date. These organocatalysts have also been immobilized to a variety of solid supports, including magneto-nanoparticles.

  本申请描述了一种新型的吡啶甲酰喹诺酮有机催化剂，可以成功地将酮亚胺转化为手性胺，具有非常高的对映选择性，并且具有迄今为止报道的任何特定有机催化剂中最高的TOFs。这些有机催化剂还被固定在各种固体支撑物上，包括磁性纳米颗粒。
• 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.
• US9844773B2
  申请人：——

  公开号：US9844773B2

  公开（公告）日：2017-12-19
• [EN] PROCESS FOR THE STEREOSELECTIVE REDUCTION OF KETOIMINES CATALYSED BY TRICHLOROSILANE<br/>[FR] PROCÉDÉ POUR LA RÉDUCTION STÉRÉOSÉLECTIVE DE CÉTOIMINES CATALYSÉES PAR LE TRICHLOROSILANE
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2009068284A2

  公开（公告）日：2009-06-04

  The invention relates to a process for the preparation of enantiomerically enriched amines from ketoimines with trichlorosilane in the presence of picolinic acid derivatives of general formula (I) wherein R1-R7 are as defined in the description as catalysts.
• Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan
  作者：Margherita Pirola、Alessandra Puglisi、Laura Raimondi、Alessandra Forni、Maurizio Benaglia

  DOI：10.3390/molecules24122260

  日期：——

  agent in the presence of a chiral Lewis base. The absolute configuration of the key intermediate was unambiguously assigned by X-ray analysis. The synthesis was also investigated exploiting continuous flow reactions; that is, an advanced intermediate of the target molecule was synthesized in only two in-flow synthetic modules, avoiding isolation and purifications of intermediates, leading to the isolation

  已经分批研究了一种立体选择性合成策略，用于制备三氟甲胺模拟物的三氟甲胺模拟物，涉及非对映选择性、无金属催化步骤，并以良好的收率和高非对映选择性提供目标分子。合成顺序的一个关键点是在手性路易斯碱的存在下用三氯硅烷作为还原剂催化还原氟化烯胺。通过 X 射线分析明确指定了关键中间体的绝对构型。还研究了利用连续流动反应的合成；也就是说，目标分子的高级中间体仅在两个流入合成模块中合成，避免了中间体的分离和纯化，