(2S,3R)-4-苄基-2-(溴苯基甲基)吗啉 | 667876-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2S,3R)-4-苄基-2-(溴苯基甲基)吗啉
• 英文名称: (2S,3R)-4-benzyl-2-(bromophenylmethyl)morpholine
• 英文别名: (2S)-4-benzyl-2-[(R)-bromo(phenyl)methyl]morpholine；(2S)-2-[(R)-bromo(phenyl)methyl]-4-(phenylmethyl)morpholine；(2S)-4-Benzyl-2-[bromo(phenyl)methyl]morpholine
• CAS: 667876-79-1
• 化学式: C₁₈H₂₀BrNO
• 分子量: 346.267
• InChiKey: WMUZKVNYNLRIEN-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-4-苄基-2-(溴苯基甲基)吗啉 在 1-氯乙基氯甲酸酯 、 potassium tert-butylate 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 30.17h， 生成 泼西汀
  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
• 作为产物：
  描述：

  (2R,3S)-4-benzyl-2-(hydroxyphenylmethyl)morpholin-3-one 在 硼烷四氢呋喃络合物 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2S,3R)-4-苄基-2-(溴苯基甲基)吗啉
  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

• [EN] PYRIDINYLMORPHOLINE DERIVATIVES<br/>[FR] DERIVES DE PYRIDINYLMORPHOLINE
  申请人：LILLY CO ELI

  公开号：WO2005023802A1

  公开（公告）日：2005-03-17

  The invention relates to compounds of formula (I); wherein R, R1, R2 and X are as defined herein, their preparation and their use as pharmaceuticals.

  这项发明涉及到式(I)的化合物；其中R、R1、R2和X如本文所定义，它们的制备以及它们作为药物的用途。
• [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。
• Morpholine derivatives
  申请人：Walter Wilhelm Magnus

  公开号：US20060035894A1

  公开（公告）日：2006-02-16

  Compounds of formula (I): wherein A is S or O; R is H; Ar is an optionally substituted phenyl group; X is an optionally substituted phenyl group, a C 1 -C 4 alkyl, a C 3 -C 6 cycloalkyl group or a CH 2 (C 3 -C 6 cycloalkyl) group; R′ is H or C 1 -C 4 alkyl; and each R 1 is independently H or C 1 -C 4 alkyl; and pharmaceutically acceptable salts thereof are selective inhibitors of norepinephrine reuptake.

  分子式为（I）的化合物：其中A为S或O；R为H；Ar为可选取代的苯基；X为可选取代的苯基、C1-C4烷基、C3-C6环烷基或CH2（C3-C6环烷基）基；R'为H或C1-C4烷基；每个R1独立地为H或C1-C4烷基；以及其药物可接受的盐是去甲肾上腺素再摄取的选择性抑制剂。
• 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。
• 2-(phenoxymethyl)-and 2-(phenylthiomethyl)-morpholine derivatives for use as selective norepinephrine reuptake inhibitors
  申请人：Eli Lilly and Company

  公开号：US07384941B2

  公开（公告）日：2008-06-10

  Compounds of formula (I): wherein A is S or O; R is H; Ar is an optionally substituted phenyl group; X is an optionally substituted phenyl group, a C1-C4 alkyl, a C3-C6 cycloalkyl group or a CH2(C3-C6 cycloalkyl) group; R′ is H or C1-C4 alkyl; and each R1 is independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof are selective inhibitors of norepinephrine reuptake.

  式(I)的化合物：其中A为S或O；R为H；Ar为可选取代的苯基团；X为可选取代的苯基团、C1-C4烷基、C3-C6环烷基或CH2(C3-C6环烷基)基；R′为H或C1-C4烷基；每个R1独立地为H或C1-C4烷基；以及其药学上可接受的盐，是去甲肾上腺素再摄取的选择性抑制剂。