(-)-N-benzoyl-ephedrine | 41958-65-0

• 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: (-)-N-benzoyl-ephedrine
• 英文别名: (-)-N-Benzoyl-ephedrin；N-((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-aethyl)-N-metthyl-benzamid; N-Benzoyl-(-)-ephedrin；N-benzoyl ephedrine；N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylbenzamide
• CAS: 41958-65-0
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: RLEBYZJBMZZXSZ-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-N-benzoyl-ephedrine 在 镍 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以69.5%的产率得到N-苯甲酰基脱氧麻黄碱
  参考文献：
  名称：

  WO2006/67794

  摘要：

  公开号：
• 作为产物：
  描述：

  麻黄碱 、 苯甲酰氯 在 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 反应 1.5h， 以78%的产率得到(-)-N-benzoyl-ephedrine
  参考文献：
  名称：

  WO2006/67794

  摘要：

  公开号：

文献信息

• A Process for the Preparation of R-(-)-N, Alpha-Dimethylphenethylamine (Levmethamfetamine) or S-(+)-N, Alpha-Dimethylphenethylamine (Methamphetamine) from D-Ephendrine, or L-Ephedrine Respectively
  申请人：Gollapudy Subrahmanyam

  公开号：US20080293971A1

  公开（公告）日：2008-11-27

  A process for synthesis of R-(−)-N,α-Dimethylphenethylamine (Levmetamfetamine, formula I), or S-(+)-N,α-Dimethyl phenethylamine (Methamphetamine, formula II), from d-ephedrine of formula III or l-ephedrine formula IV, the process comprising the steps of (a) acylating the d- or l-ephedrine base of formula III or formula IV with an acylating agent to make a reaction mixture containing a N-acylated ephedrines of formula V or formula VI; (b) deoxygenation of N-acylated ephedrines to make the compound of the formula VII or Formula VIII by using Raney Nickel catalyst; and (c) acid hydrolysis of the above deoxygenated products to get the levmetamfetamine or methamphetamine.

  一种从d-麻黄碱（式III）或l-麻黄碱（式IV）合成R-（-）-N，α-二甲基苯乙胺（左旋甲基苯丙胺，式I）或S-（+）-N，α-二甲基苯乙胺（甲基苯丙胺，式II）的方法，该方法包括以下步骤：（a）用酰化剂酰化式III或式IV的d-或l-麻黄碱基，制备含有式V或式VI的N-酰化麻黄碱的反应混合物；（b）使用Raney镍催化剂脱氧N-酰化麻黄碱，制备式VII或式VIII的化合物；（c）对上述脱氧产物进行酸水解，得到左旋甲基苯丙胺或甲基苯丙胺。
• Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis
  作者：Miguel Yus、Francisco Foubelo、Larry R. Falvello

  DOI：10.1016/0957-4166(95)00271-p

  日期：1995.8

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.
• 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.
• Mechanism and Stereochemical Course of Acyl Migrations in Derivatives of Ephedrine and ψ-Ephedrine
  作者：Llewellyn H. Welsh

  DOI：10.1021/ja01178a071

  日期：1949.10
• Kanao, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1928, vol. 48, p. 145,1076
  作者：Kanao

  DOI：——

  日期：——