(S)-5-(4-methoxyphenoxymethyl)-1,3-oxazolidin-2-one | 852805-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-5-(4-methoxyphenoxymethyl)-1,3-oxazolidin-2-one
• 英文别名: (5S)-5-[(4-methoxyphenoxy)methyl]-1,3-oxazolidin-2-one
• CAS: 852805-35-7
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: QYZDEEHEJPYXDQ-JTQLQIEISA-N

物化性质

• 沸点：
  466.5±18.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-(4-methoxyphenoxymethyl)-1,3-oxazolidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以45%的产率得到(5S)-5-(羟甲基)-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  New chemoenzymatic pathway for β-adrenergic blocking agents

  摘要：

  The lipase mediated kinetic resolution of pharmaceutically important beta-hydroxy nitrites is described in high enantionteric excesses and good yields. Some of the chiral beta-hydroxy nitriles have been employed in the synthesis of P-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-liydroxy-4-tosyloxybutaiieiiitrile, chiral intermediates of high synthetic value. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.015
• 作为产物：
  描述：

  (S)-3-hydroxy-4-(4-methoxyphenoxy)butanamide 在 吡啶 、 lead(IV) acetate 作用下， 反应 1.5h， 以80%的产率得到(S)-5-(4-methoxyphenoxymethyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  New chemoenzymatic pathway for β-adrenergic blocking agents

  摘要：

  The lipase mediated kinetic resolution of pharmaceutically important beta-hydroxy nitrites is described in high enantionteric excesses and good yields. Some of the chiral beta-hydroxy nitriles have been employed in the synthesis of P-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-liydroxy-4-tosyloxybutaiieiiitrile, chiral intermediates of high synthetic value. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.015

文献信息

• New chemoenzymatic pathway for β-adrenergic blocking agents
  作者：Ahmed Kamal、G.B. Ramesh Khanna、T. Krishnaji、Venkatesh Tekumalla、R. Ramu

  DOI：10.1016/j.tetasy.2005.02.015

  日期：2005.4

  The lipase mediated kinetic resolution of pharmaceutically important beta-hydroxy nitrites is described in high enantionteric excesses and good yields. Some of the chiral beta-hydroxy nitriles have been employed in the synthesis of P-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-liydroxy-4-tosyloxybutaiieiiitrile, chiral intermediates of high synthetic value. (c) 2005 Elsevier Ltd. All rights reserved.