(1'S,2S,3S)-(-)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl-N-(1'-phenyl-ethyl)propionamide | 1215207-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1'S,2S,3S)-(-)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl-N-(1'-phenyl-ethyl)propionamide
• 英文别名: (2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl-N-[(1S)-1-phenylethyl]propanamide
• CAS: 1215207-24-1
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: GYMFUFXRSHKVCU-NWVWQQAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (1'S,2S,3S)-(-)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl-N-(1'-phenyl-ethyl)propionamide 在 dimethyl sulfide borane 作用下， 反应 8.0h， 以75%的产率得到(1'S,2R,3S)-(-)-1-(2-ethoxyphenoxy)-1-phenyl-3-(1'-phenyl-ethylamino)propan-2-ol
  参考文献：
  名称：

  Application of amide-stabilized sulfur ylide reactivity to the stereodivergent synthesis of (R,S)- and (S,R)-reboxetine

  摘要：

  A simple access to (RS)- and (S,R)-reboxetine from a single chiral sulfonium salt 4 is reported. This approach, based on a stabilized sulfur ylide-mediated epoxidation, followed by a regioselective opening reaction, enables the preparation of these two potentially biologically active compounds in 35.6% and 13.7% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.004
• 作为产物：
  描述：

  2-ethoxyphenoxy sodium salt 、 dimethyl-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]sulfanium 、 苯甲醛 在 potassium tert-butylate 、 18-冠醚-6 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 31.0h， 生成 (1'S,2R,3R)-(-)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl-N-(1'-phenyl-ethyl)propionamide 、 (1'S,2S,3S)-(-)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl-N-(1'-phenyl-ethyl)propionamide
  参考文献：
  名称：

  Application of amide-stabilized sulfur ylide reactivity to the stereodivergent synthesis of (R,S)- and (S,R)-reboxetine

  摘要：

  A simple access to (RS)- and (S,R)-reboxetine from a single chiral sulfonium salt 4 is reported. This approach, based on a stabilized sulfur ylide-mediated epoxidation, followed by a regioselective opening reaction, enables the preparation of these two potentially biologically active compounds in 35.6% and 13.7% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.004

文献信息

• Application of amide-stabilized sulfur ylide reactivity to the stereodivergent synthesis of (R,S)- and (S,R)-reboxetine
  作者：David M. Aparicio、Joel L. Terán、Dino Gnecco、Alberto Galindo、Jorge R. Juárez、María L. Orea、Angel Mendoza

  DOI：10.1016/j.tetasy.2009.12.004

  日期：2009.12

  A simple access to (RS)- and (S,R)-reboxetine from a single chiral sulfonium salt 4 is reported. This approach, based on a stabilized sulfur ylide-mediated epoxidation, followed by a regioselective opening reaction, enables the preparation of these two potentially biologically active compounds in 35.6% and 13.7% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.