3-methoxy-4-methoxycarbonyloxycinnamoyl chloride

• 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: 3-methoxy-4-methoxycarbonyloxycinnamoyl chloride
• 英文别名: [4-[(E)-3-chloro-3-oxoprop-1-enyl]-2-methoxyphenyl] methyl carbonate
• 化学式: C₁₂H₁₁ClO₅
• 分子量: 270.669
• InChiKey: ONPNKAFKVDEIPB-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-methoxycarbonyloxycinnamoyl chloride 在 吡啶 、 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 butane 1,4-di-(3-methoxy-4-hydroxy)cinnamate
  参考文献：
  名称：

  Effect of Substitution on the 2+2 Cycloaddition Reaction of Phenylpropanoids

  摘要：

  Formation of the cyclobutane products truxillic and truxinic acid within the plant cell wall could occur by photocycloaddition or possibly by enzyme-mediated radical coupling. Model precursors were synthesized and the mode of formation of the cyclobutane products was investigated. Modeling studies suggested that all the model compounds with the exception of the 2-hydroxylated diester contained the correct geometry for photocyclization and this was confirmed by irradiation. Delocalization of the unpaired electron was measured by ESR and the photochemical reaction rates were compared with the partial atomic orbital population of the singly occupied molecular orbital. It was observed that the 3-hydroxylated derivative had almost no delocalization to C8 and the lowest reaction rate. The rate of reaction increased with increasing extent of methoxylation. Incubation with silver oxide or with peroxidase failed to induce intramolecular dimerization. These results suggest that the biological mode of formation of truxillic and truxinic acid is the most likely via light-catalyzed 2+2 cycloaddition. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1143
• 作为产物：
  描述：

  阿魏酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 5.5h， 生成 3-methoxy-4-methoxycarbonyloxycinnamoyl chloride
  参考文献：
  名称：

  Effect of Substitution on the 2+2 Cycloaddition Reaction of Phenylpropanoids

  摘要：

  Formation of the cyclobutane products truxillic and truxinic acid within the plant cell wall could occur by photocycloaddition or possibly by enzyme-mediated radical coupling. Model precursors were synthesized and the mode of formation of the cyclobutane products was investigated. Modeling studies suggested that all the model compounds with the exception of the 2-hydroxylated diester contained the correct geometry for photocyclization and this was confirmed by irradiation. Delocalization of the unpaired electron was measured by ESR and the photochemical reaction rates were compared with the partial atomic orbital population of the singly occupied molecular orbital. It was observed that the 3-hydroxylated derivative had almost no delocalization to C8 and the lowest reaction rate. The rate of reaction increased with increasing extent of methoxylation. Incubation with silver oxide or with peroxidase failed to induce intramolecular dimerization. These results suggest that the biological mode of formation of truxillic and truxinic acid is the most likely via light-catalyzed 2+2 cycloaddition. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1143

文献信息

• Synthesis of Dicarbonyl Curcumin Analogues Containing the Tropane Scaffold
  作者：Karol Wolosewicz、Katarzyna Podgorska、Ewelina Rutkowska、Ryszard Lazny

  DOI：10.1002/ejoc.201900416

  日期：2019.8.7

  The first synthesis of tropane based 1,3‐dicarbonyl curcumin analogues. A general methodology for preparation of diversely substituted diarylheptanoid systems fused with tropane moiety is presented.

  首次合成基于托烷的1,3-二羰基姜黄素类似物。提出了制备与托烷部分融合的不同取代的二芳基庚烷体系的一般方法。