(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3-methoxy-phenyl)-allyl ester | 213185-30-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3-methoxy-phenyl)-allyl ester
• 英文别名: [(E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enyl] (E)-3-(4-acetyloxyphenyl)prop-2-enoate
• CAS: 213185-30-9
• 化学式: C₂₃H₂₂O₇
• 分子量: 410.423
• InChiKey: JFHOSKHEYFVNDM-CCKNLQGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3-methoxy-phenyl)-allyl ester 在 四氢吡咯 作用下， 以93%的产率得到Coniferyl p-coumarate
  参考文献：
  名称：

  Facile Synthesis of 4-Hydroxycinnamyl p-Coumarates

  摘要：

  Coniferyl p-coumarate (4-hydroxy-3-methoxycinnamyl 4-hydroxycinnamate) and sinapyl p-coumarate (3,5-dimethoxy-4-hydroxycinnamyl 4-hydroxycinnamate) were synthesized in high overall yield. In this improved method acetate was used as the phenol protecting group instead of 2,4-dinitrophenyl ether; selective deacetylation, without cinnamate ester hydrolysis, was accomplished with neat pyrrolidine.

  DOI：

  10.1021/jf980440y
• 作为产物：
  描述：

  反式-4-乙酰氧基肉桂酸 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3-methoxy-phenyl)-allyl ester
  参考文献：
  名称：

  Facile Synthesis of 4-Hydroxycinnamyl p-Coumarates

  摘要：

  Coniferyl p-coumarate (4-hydroxy-3-methoxycinnamyl 4-hydroxycinnamate) and sinapyl p-coumarate (3,5-dimethoxy-4-hydroxycinnamyl 4-hydroxycinnamate) were synthesized in high overall yield. In this improved method acetate was used as the phenol protecting group instead of 2,4-dinitrophenyl ether; selective deacetylation, without cinnamate ester hydrolysis, was accomplished with neat pyrrolidine.

  DOI：

  10.1021/jf980440y

文献信息

• Facile Synthesis of 4-Hydroxycinnamyl <i>p</i>-Coumarates
  作者：Fachuang Lu、John Ralph

  DOI：10.1021/jf980440y

  日期：1998.8.17

  Coniferyl p-coumarate (4-hydroxy-3-methoxycinnamyl 4-hydroxycinnamate) and sinapyl p-coumarate (3,5-dimethoxy-4-hydroxycinnamyl 4-hydroxycinnamate) were synthesized in high overall yield. In this improved method acetate was used as the phenol protecting group instead of 2,4-dinitrophenyl ether; selective deacetylation, without cinnamate ester hydrolysis, was accomplished with neat pyrrolidine.