(1'S,6R)-(+)-6-[(S)-(2-ethoxyphenoxy)phenylmethyl]-4-(1'-phenylethyl)morpholin-3-one | 1215207-28-5

• 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,6R)-(+)-6-[(S)-(2-ethoxyphenoxy)phenylmethyl]-4-(1'-phenylethyl)morpholin-3-one
• CAS: 1215207-28-5
• 化学式: C₂₇H₂₉NO₄
• 分子量: 431.532
• InChiKey: RQAUZADIBJBDLB-FESMNKHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1'S,6R)-(+)-6-[(S)-(2-ethoxyphenoxy)phenylmethyl]-4-(1'-phenylethyl)morpholin-3-one 在 dimethyl sulfide borane 作用下， 反应 8.0h， 以95%的产率得到(1'S,2R,2aS)-(-)-2-[(2-ethoxyphenoxy)phenylmethyl]-4-(1'-phenylethyl)morpholine
  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：

  (1'S,2R,3S)-(-)-2-bromo-N-[3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]-N-(1'-phenylethyl)acetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(1'S,6R)-(+)-6-[(S)-(2-ethoxyphenoxy)phenylmethyl]-4-(1'-phenylethyl)morpholin-3-one
  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