N-[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]-2-chloroacetamide | 1384288-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]-2-chloroacetamide
• 英文别名: 2-chloro-N-[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]acetamide
• CAS: 1384288-64-5
• 化学式: C₁₉H₂₂ClNO₄
• 分子量: 363.841
• InChiKey: PPLKMZSFXPAVNG-BEFAXECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]-2-chloroacetamide 在 dimethyl sulfide borane 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 1.0h， 生成 (2R,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine
  参考文献：
  名称：

  The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement—opening process

  摘要：

  (R,S)-Reboxetine was synthesized in nine steps and with 43% overall yield starting from trans-cinnamyl alcohol. Following silylation and AD steps, the two hydroxyl groups at C-1 and C-2 were simultaneously activated to the cyclic sulfate. A series of tandem reactions initiated by desilylation transposed the activation to C-3, then to C-1, where nucleophilic displacements took place in succession. During this process, the configuration at C-2 was inverted while that at C-1 was retained through a double inversion. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.018
• 作为产物：
  描述：

  (E)-1-tert-butyldimethylsilyloxy-3-phenyl-2-propene 在 sodium periodate 、 氯化亚砜 、 甲基磺酰胺 、 ruthenium(III) chloride trihydrate 、 AD-mix α 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 水 、 氢气 、 碳酸氢钠 、 三乙胺 作用下， 以 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 、 叔丁醇 为溶剂， 反应 11.17h， 生成 N-[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]-2-chloroacetamide
  参考文献：
  名称：

  The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement—opening process

  摘要：

  (R,S)-Reboxetine was synthesized in nine steps and with 43% overall yield starting from trans-cinnamyl alcohol. Following silylation and AD steps, the two hydroxyl groups at C-1 and C-2 were simultaneously activated to the cyclic sulfate. A series of tandem reactions initiated by desilylation transposed the activation to C-3, then to C-1, where nucleophilic displacements took place in succession. During this process, the configuration at C-2 was inverted while that at C-1 was retained through a double inversion. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.018

文献信息

• The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement—opening process
  作者：Jin Yu、Soo Y. Ko

  DOI：10.1016/j.tetasy.2012.04.018

  日期：2012.5

  (R,S)-Reboxetine was synthesized in nine steps and with 43% overall yield starting from trans-cinnamyl alcohol. Following silylation and AD steps, the two hydroxyl groups at C-1 and C-2 were simultaneously activated to the cyclic sulfate. A series of tandem reactions initiated by desilylation transposed the activation to C-3, then to C-1, where nucleophilic displacements took place in succession. During this process, the configuration at C-2 was inverted while that at C-1 was retained through a double inversion. (C) 2012 Elsevier Ltd. All rights reserved.