4-甲氧基-3-[3-(4-甲氧基苯基)-1-氧代丙基]-苯丙酸 | 13577-08-7

• 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
• 中文名称: 4-甲氧基-3-[3-(4-甲氧基苯基)-1-氧代丙基]-苯丙酸
• 英文名称: p-methoxy-3-(p-methoxyhydrocinnamoyl)hydrocinnamic acid
• 英文别名: 3-[4-Methoxy-3-[3-(4-methoxyphenyl)propanoyl]phenyl]propanoic acid
• CAS: 13577-08-7
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: RYQBCYLFAYJFIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  4-甲氧基-3-[3-(4-甲氧基苯基)-1-氧代丙基]-苯丙酸 在 四丁基溴化铵 氢氧化钾 、 sodium hydroxide 、 PPA 、 Polyphosphoric acid (PPA) 、 一水合肼 、 硫酸二甲酯 作用下， 反应 2.0h， 生成 5,14-dimethoxy<3.3>metacyclophane
  参考文献：
  名称：

  Polyphosphoric acid catalyzed conversion of 3-(methoxyphenyl)propionic acids to derivatives of [3.3]metacyclophane-1,10-diones and 1-indanones

  摘要：

  Polyphosphoric acid (PPA) catalyzed cycliacylation of 3-(2-methoxy- and 2,4-dimethoxyphenyl)propionic acids (1a,b) results in dimeric products: 46 and 49% yields of 5,14-dimethoxy- and 5,7,14,16-tetramethoxy[3.3]metacyclophane-1,10-diones(5a,b) and a 2.5% yield of 4-methoxy-1-indanone (3a), isolated by steam distillation. 3-(4-Methoxyphenyl)propionic acid (1c), depending upon the ratio of PPA/1c, gives 17-65% yields of steam-distilled 6-methoxy-1-indanone (3c). This latter reaction also gives low yields of 7,16-dimethoxy[3.3]metacyclophane-1,10-dione (5c) and an intermediate, dimeric keto acid p-methoxy-3-(p-methoxyhydrocinnamoyl)hydrocinnamic acid (4c) (C20H22O5). The latter was cyclized in PPA to 5c in 44% yield. Wolff-Kishner reduction converts 5a and 5c to 5,14-dimethoxy[3.3]metacyclophane (6a) and 5b to 5,7,14,16-tetramethoxy[3.3]metacyclophane (6b). Single-crystal X-ray studies of 5a show the aromatic rings are in the anti conformation whereas the solid-state structure of 6b is in the syn conformation.

  DOI：

  10.1021/jo00055a005
• 作为产物：
  描述：

  3-(4-甲氧基苯基)丙酸 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 反应 0.5h， 以65%的产率得到6-甲氧基-1-茚酮
  参考文献：
  名称：

  Polyphosphoric acid catalyzed conversion of 3-(methoxyphenyl)propionic acids to derivatives of [3.3]metacyclophane-1,10-diones and 1-indanones

  摘要：

  Polyphosphoric acid (PPA) catalyzed cycliacylation of 3-(2-methoxy- and 2,4-dimethoxyphenyl)propionic acids (1a,b) results in dimeric products: 46 and 49% yields of 5,14-dimethoxy- and 5,7,14,16-tetramethoxy[3.3]metacyclophane-1,10-diones(5a,b) and a 2.5% yield of 4-methoxy-1-indanone (3a), isolated by steam distillation. 3-(4-Methoxyphenyl)propionic acid (1c), depending upon the ratio of PPA/1c, gives 17-65% yields of steam-distilled 6-methoxy-1-indanone (3c). This latter reaction also gives low yields of 7,16-dimethoxy[3.3]metacyclophane-1,10-dione (5c) and an intermediate, dimeric keto acid p-methoxy-3-(p-methoxyhydrocinnamoyl)hydrocinnamic acid (4c) (C20H22O5). The latter was cyclized in PPA to 5c in 44% yield. Wolff-Kishner reduction converts 5a and 5c to 5,14-dimethoxy[3.3]metacyclophane (6a) and 5b to 5,7,14,16-tetramethoxy[3.3]metacyclophane (6b). Single-crystal X-ray studies of 5a show the aromatic rings are in the anti conformation whereas the solid-state structure of 6b is in the syn conformation.

  DOI：

  10.1021/jo00055a005