(S)-1-{2-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]phenoxy}-3-propylamino-2-propanol | 189766-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-1-{2-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]phenoxy}-3-propylamino-2-propanol
• 英文别名: (2S)-1-[2-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]phenoxy]-3-(propylamino)propan-2-ol
• CAS: 189766-51-6
• 化学式: C₂₃H₃₁NO₄
• 分子量: 385.503
• InChiKey: SXWSZUDXVUYTPC-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-{2-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]phenoxy}-3-propylamino-2-propanol 在 盐酸 作用下， 反应 1.0h， 生成 1-[2-[(2R)-2-羟基-3-丙基氨基丙氧基]苯基]-3-苯基丙烷-1-酮盐酸盐 、 1-[2-[(2S)-2-羟基-3-丙基氨基丙氧基]苯基]-3-苯基丙烷-1-酮盐酸盐
  参考文献：
  名称：

  Improved synthesis of the enantiomers of propafenone using chiral building blocks

  摘要：

  A short and efficient synthesis of the enantiomers of the antiarrhythmic drug propafenone (1) is described using both (R)-isopropylidenegrycerol tosylate and (S)-glycidyl tosylate as chiral building blocks. The key step of the high yield synthesis is the acetalization of the carbonyl group in 1-(2-hydroxyphenyl)-3-phenyl-1-propanone (2) which allows application of mild reaction conditions in the subsequent alkylation of the phenolic hydroxy group.

  DOI：

  10.1007/bf00807638
• 作为产物：
  描述：

  2'-羟基-3-苯基苯丙酮 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 91.0h， 生成 (S)-1-{2-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]phenoxy}-3-propylamino-2-propanol
  参考文献：
  名称：

  Improved synthesis of the enantiomers of propafenone using chiral building blocks

  摘要：

  A short and efficient synthesis of the enantiomers of the antiarrhythmic drug propafenone (1) is described using both (R)-isopropylidenegrycerol tosylate and (S)-glycidyl tosylate as chiral building blocks. The key step of the high yield synthesis is the acetalization of the carbonyl group in 1-(2-hydroxyphenyl)-3-phenyl-1-propanone (2) which allows application of mild reaction conditions in the subsequent alkylation of the phenolic hydroxy group.

  DOI：

  10.1007/bf00807638

文献信息

• Improved synthesis of the enantiomers of propafenone using chiral building blocks
  作者：G. Ecker、C. R. Noe、W. Fleischhacker

  DOI：10.1007/bf00807638

  日期：1997.1

  A short and efficient synthesis of the enantiomers of the antiarrhythmic drug propafenone (1) is described using both (R)-isopropylidenegrycerol tosylate and (S)-glycidyl tosylate as chiral building blocks. The key step of the high yield synthesis is the acetalization of the carbonyl group in 1-(2-hydroxyphenyl)-3-phenyl-1-propanone (2) which allows application of mild reaction conditions in the subsequent alkylation of the phenolic hydroxy group.