Toluene-4-sulfonic acid (S)-2-hydroxy-3-[2-(3-phenyl-propionyl)-phenoxy]-propyl ester | 189766-48-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Toluene-4-sulfonic acid (S)-2-hydroxy-3-[2-(3-phenyl-propionyl)-phenoxy]-propyl ester
• 英文别名: [(2S)-2-hydroxy-3-[2-(3-phenylpropanoyl)phenoxy]propyl] 4-methylbenzenesulfonate
• CAS: 189766-48-1
• 化学式: C₂₅H₂₆O₆S
• 分子量: 454.544
• InChiKey: BTLZVYVORKBJLA-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  正丙胺 、 Toluene-4-sulfonic acid (S)-2-hydroxy-3-[2-(3-phenyl-propionyl)-phenoxy]-propyl ester 在 盐酸 作用下， 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 盐酸 、 sodium hydride 、 对甲苯磺酸 、 potassium iodide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 123.0h， 生成 Toluene-4-sulfonic acid (S)-2-hydroxy-3-[2-(3-phenyl-propionyl)-phenoxy]-propyl ester
  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.