3-(2-methyl-4-phenylacetoxyphenyl)propionic acid | 137644-79-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2-methyl-4-phenylacetoxyphenyl)propionic acid
• 英文别名: 3-[2-methyl-4-(2-phenylacetyl)oxyphenyl]propanoic acid
• CAS: 137644-79-2
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: WVVBNAWLNDQVNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(2-methyl-4-phenylacetoxyphenyl)propionic acid 在 草酰氯 作用下， 以 乙醚 、 苯 为溶剂， 反应 2.17h， 生成 2-diazo-5-(2-methyl-4-phenylacetoxyphenyl)pentan-3-one
  参考文献：
  名称：

  Pseudoguaianolides from intramolecular cycloadditions of aryl diazoketones: synthesis of (±)-confertin and an approach to the synthesis of (±)-damsin

  摘要：

  Rhodium(II) mandelate-catalysed cyclisation of alpha-diazoketones derived from 3-arylpropionic acids produces bicyclo[5.3.0]decatrienones, one of which has been used to synthesise an advanced (+/-)-confertin intermediate in six stages and 20% overall yield. The possibility of constructing intermediates for the synthesis of damsin-like pseudoguaianolides via catalysed diazoketone cyclisation is also examined and methods for the construction of polyfunctional 3-arylpropionic acids suitable for use as damsin precursors are presented.

  DOI：

  10.1039/p19910002565
• 作为产物：
  描述：

  3-(4-hydroxy-2-methylphenyl)propionic acid 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 25.0 ℃ 、172.37 kPa 条件下， 反应 14.25h， 生成 3-(2-methyl-4-phenylacetoxyphenyl)propionic acid
  参考文献：
  名称：

  Pseudoguaianolides from intramolecular cycloadditions of aryl diazoketones: synthesis of (±)-confertin and an approach to the synthesis of (±)-damsin

  摘要：

  Rhodium(II) mandelate-catalysed cyclisation of alpha-diazoketones derived from 3-arylpropionic acids produces bicyclo[5.3.0]decatrienones, one of which has been used to synthesise an advanced (+/-)-confertin intermediate in six stages and 20% overall yield. The possibility of constructing intermediates for the synthesis of damsin-like pseudoguaianolides via catalysed diazoketone cyclisation is also examined and methods for the construction of polyfunctional 3-arylpropionic acids suitable for use as damsin precursors are presented.

  DOI：

  10.1039/p19910002565