1-[2-((R)-2,3-Dihydroxy-propoxy)-phenyl]-3-phenyl-propan-1-one | 189766-47-0

• 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: 1-[2-((R)-2,3-Dihydroxy-propoxy)-phenyl]-3-phenyl-propan-1-one
• 英文别名: 1-[2-[(2R)-2,3-dihydroxypropoxy]phenyl]-3-phenylpropan-1-one
• CAS: 189766-47-0
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: KRSTZDUMPGTWJG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-((R)-2,3-Dihydroxy-propoxy)-phenyl]-3-phenyl-propan-1-one 在 盐酸 作用下， 以 吡啶 为溶剂， 反应 19.0h， 生成 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 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 107.0h， 生成 1-[2-((R)-2,3-Dihydroxy-propoxy)-phenyl]-3-phenyl-propan-1-one
  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.