(2R,3S)-4-benzyl-2-(hydroxy-p-tolylmethyl)morpholin-3-one | 1450995-70-6

• 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: (2R,3S)-4-benzyl-2-(hydroxy-p-tolylmethyl)morpholin-3-one
• 英文别名: (2R)-2-[(S)-(4-methylphenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one；(2R)-4-benzyl-2-[(S)-hydroxy-(4-methylphenyl)methyl]morpholin-3-one
• CAS: 1450995-70-6
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: LFSIFAJCEDPTLH-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-4-benzyl-2-(hydroxy-p-tolylmethyl)morpholin-3-one 、 (2S)-2-[(R)-(4-methylphenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one 生成 (2R)-2-[(R)-(4-methylphenyl)(hydroxy)methyl]-4-benzylmorpholine 、 (2S)-2-[(S)-(4-methylphenyl)(hydroxy)methyl]-4-benzylmorpholine
  参考文献：
  名称：

  [EN] BENZYL MORPHOLINE DERIVATIVES
  [FR] DERIVES DE LA BENZYL MORPHOLINE

  摘要：

  化合物的化学式（I）（I），其中R为H；Ar为从苯基中选择的芳香基团；X为苯基团；R'为H或C1-C4烷基；每个R1独立地为H或C1-C4烷基；以及其药用可接受的盐。

  公开号：

  WO2004018440A1
• 作为产物：
  描述：

  (4-甲基苯基)吗啉-4-基甲酮 在 RuCl[(R,R)-TsDPEN](mesitylene) 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (2R,3S)-4-benzyl-2-(hydroxy-p-tolylmethyl)morpholin-3-one
  参考文献：
  名称：

  Dynamic Kinetic Resolution-Based Asymmetric Transfer Hydrogenation of 2-Benzoylmorpholinones and Its Use in Concise Stereoselective Synthesis of All Four Stereoisomers of the Antidepressant Reboxetine

  摘要：

  Dynamic kinetic resolution-driven, asymmetric transfer hydrogenation reaction of 2-benzoylmorpholin-3-ones (4) proceeds efficiently to give the corresponding (2R,3S)- or (2S,3R)-2-(hydroxyphenylmethyl)morpholin-3-ones (6) with an excellent level of diastereo- and enantioselectivity and simultaneous control of two contiguous stereogenic centers in a single step. This process is employed to prepare all four stereoisomers of the antidepressant reboxetine.

  DOI：

  10.1021/jo401102d

文献信息

• Benzyl morpholine derivatives
  申请人：Clark Peter Barry

  公开号：US20060052377A1

  公开（公告）日：2006-03-09

  A compound of formula (I) (I) wherein R is H; Ar is an aromatic group selected from phenyl; X is a phenyl group; R′ H or C1-C4 alkyl; each R1 is independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof.

  化合物的式(I)，其中R是H；Ar是从苯基选择的芳香基；X是苯基；R′是H或C1-C4烷基；每个R1独立地是H或C1-C4烷基；以及其药学上可接受的盐。
• BENZYL MORPHOLINE DERIVATIVES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1546123A1

  公开（公告）日：2005-06-29
• US7294623B2
  申请人：——

  公开号：US7294623B2

  公开（公告）日：2007-11-13
• [EN] BENZYL MORPHOLINE DERIVATIVES<br/>[FR] DERIVES DE LA BENZYL MORPHOLINE
  申请人：LILLY CO ELI

  公开号：WO2004018440A1

  公开（公告）日：2004-03-04

  A compound of formula (I) (I)wherein R is H; Ar is an aromatic group selected from phenyl; X is a phenyl group; R' is H or C1-C4 alkyl; each R1 is independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof.

  化合物的化学式（I）（I），其中R为H；Ar为从苯基中选择的芳香基团；X为苯基团；R'为H或C1-C4烷基；每个R1独立地为H或C1-C4烷基；以及其药用可接受的盐。
• Dynamic Kinetic Resolution-Based Asymmetric Transfer Hydrogenation of 2-Benzoylmorpholinones and Its Use in Concise Stereoselective Synthesis of All Four Stereoisomers of the Antidepressant Reboxetine
  作者：Se-Mi Son、Hyeon-Kyu Lee

  DOI：10.1021/jo401102d

  日期：2013.9.6

  Dynamic kinetic resolution-driven, asymmetric transfer hydrogenation reaction of 2-benzoylmorpholin-3-ones (4) proceeds efficiently to give the corresponding (2R,3S)- or (2S,3R)-2-(hydroxyphenylmethyl)morpholin-3-ones (6) with an excellent level of diastereo- and enantioselectivity and simultaneous control of two contiguous stereogenic centers in a single step. This process is employed to prepare all four stereoisomers of the antidepressant reboxetine.