1-(4-benzylmorpholin-2-yl)-2-(2-methoxyphenyl)-ethanone | 885096-37-7

• 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: 1-(4-benzylmorpholin-2-yl)-2-(2-methoxyphenyl)-ethanone
• 英文别名: 1-(4-Benzylmorpholin-2-yl)-2-(2-methoxyphenyl)ethan-1-one；1-(4-benzylmorpholin-2-yl)-2-(2-methoxyphenyl)ethanone
• CAS: 885096-37-7
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: AMXWDQSUZYKNAR-UHFFFAOYSA-N

物化性质

• 沸点：
  452.0±45.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-benzylmorpholin-2-yl)-2-(2-methoxyphenyl)-ethanone 在 cesium fluoride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 73.0h， 生成 benzyl 2-(1-(2-methoxyphenyl)methyl-2,2,2-trifluoro-1-hydroxyethyl)morpholine-4-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of fluorinated analogues of monoamine reuptake inhibitors

  摘要：

  The synthesis of two series of fluorinated analogues of monoamines reuptake inhibitors based on tertiary alcohols 2-substituted morpholines scaffold has been achieved through the incorporation of fluorinated substituent into 2-substituted morpholino ketones. Their binding affinities have been measured on different monoamine transporters. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.02.018
• 作为产物：
  描述：

  4-苄基吗啉-2-甲腈 在 盐酸 作用下， 反应 1.5h， 生成 1-(4-benzylmorpholin-2-yl)-2-(2-methoxyphenyl)-ethanone
  参考文献：
  名称：

  Discovery of novel and selective tertiary alcohol containing inhibitors of the norepinephrine transporter

  摘要：

  A novel series of tertiary alcohol containing 2-substituted benzyl morpholines have been discovered as potent and selective inhibitors of the norepinephrine transporter. Efficient synthetic routes were developed featuring a highly diastereoselective nucleophilic addition of benzyl Grignard reagents to enantiopure (4-benzylmorpholin-2-yl)phenylmethanone (11) as the key synthetic step. In vitro binding affinity for the norepinephrine, dopamine and serotonin transporters and in vivo examination of a select compound (16) in a pharmacodynamic animal model for norepinephrine reuptake inhibition are presented. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.061

文献信息

• Synthesis and evaluation of fluorinated analogues of monoamine reuptake inhibitors
  作者：Christine Philippe、Julia Kaffy、Thierry Milcent、Danièle Bonnet-Delpon

  DOI：10.1016/j.jfluchem.2011.02.018

  日期：2012.2

  The synthesis of two series of fluorinated analogues of monoamines reuptake inhibitors based on tertiary alcohols 2-substituted morpholines scaffold has been achieved through the incorporation of fluorinated substituent into 2-substituted morpholino ketones. Their binding affinities have been measured on different monoamine transporters. (C) 2011 Elsevier B.V. All rights reserved.
• Discovery of novel and selective tertiary alcohol containing inhibitors of the norepinephrine transporter
  作者：Manuel J. Cases-Thomas、John J. Masters、Magnus W. Walter、Gordon Campbell、Louise Haughton、Peter T. Gallagher、David R. Dobson、Vincent Mancuso、Benjamin Bonnier、Thierry Giard、Thierry Defrance、Michel Vanmarsenille、Andrew Ledgard、Craig White、Sivi Ouwerkerk-Mahadevan、Francoise J. Brunelle、Nancy A. Dezutter、Camy A. Herbots、Joel Y. Lienard、Jeremy Findlay、Lorna Hayhurst、John Boot、Linda K. Thompson、Susan Hemrick-Luecke

  DOI：10.1016/j.bmcl.2005.12.061

  日期：2006.4

  A novel series of tertiary alcohol containing 2-substituted benzyl morpholines have been discovered as potent and selective inhibitors of the norepinephrine transporter. Efficient synthetic routes were developed featuring a highly diastereoselective nucleophilic addition of benzyl Grignard reagents to enantiopure (4-benzylmorpholin-2-yl)phenylmethanone (11) as the key synthetic step. In vitro binding affinity for the norepinephrine, dopamine and serotonin transporters and in vivo examination of a select compound (16) in a pharmacodynamic animal model for norepinephrine reuptake inhibition are presented. (C) 2005 Elsevier Ltd. All rights reserved.