(2S,3R)-4-benzyl-2-(hydroxyphenylmethyl)morpholin-3-one | 800407-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2S,3R)-4-benzyl-2-(hydroxyphenylmethyl)morpholin-3-one
• 英文别名: (2S)-2-[(R)-hydroxy(phenyl)methyl]-4-(phenylmethyl)morpholin-3-one；(2S)-2-[(R)-hydroxy(phenyl)methyl]-4-benzylmorpholin-3-one；(2S)-2-((alphaR)-alpha-Hydroxybenzyl)-4-benzylmorpholine-3-one；(2S)-4-benzyl-2-[(R)-hydroxy(phenyl)methyl]morpholin-3-one
• CAS: 800407-89-0
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: IIBSPZWJLYZHQR-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  (2S,3R)-4-benzyl-2-(hydroxyphenylmethyl)morpholin-3-one 在 硼烷四氢呋喃络合物 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 (2R,3S)-4-benzyl-2-[(2-ethoxyphenoxy)phenylmethyl]morpholine
  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：

  4-苯甲酰吗啉 在 C₃₀H₃₂ClN₂O₂RuS 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 (2S,3R)-4-benzyl-2-(hydroxyphenylmethyl)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

• [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。
• [EN] TREATMENT OF PERVASIVE DEVELOPMENTAL DISORDERS WITH NOREPINEPHRINE REUPTAKE INHIBITORS<br/>[FR] TRAITEMENT DES TROUBLES PROFONDS DU DEVELOPPEMENT AU MOYEN D'INHIBITEURS DE LA RECAPTURE DE LA NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2005020976A3

  公开（公告）日：2005-06-16
• [EN] SELECTIVE NOREPINEPHRINE REUPTAKE INHIBITORS FOR THE TREATMENT OF HOT FLASHES, IMPULSE CONTROL DISORDERS AND PERSONALITY CHANGE DUE TO A GENERAL MEDICAL CONDITION<br/>[FR] TRAITEMENT DES BOUFFEES DE CHALEUR, DES TROUBLES DU CONTROLE DES IMPULSIONS ET DU CHANGEMENT DE PERSONNALITE CONSECUTIFS A UN ETAT PATHOLOGIQUE GENERAL
  申请人：LILLY CO ELI

  公开号：WO2005060949A3

  公开（公告）日：2005-09-09