2-acetyl-3-methoxyphenyl (E)-3,4-dimethoxycinnamate | 1172141-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-3-methoxyphenyl (E)-3,4-dimethoxycinnamate
• 英文别名: 2-acetyl-3-methoxyphenyl (E)-2-(3,4-dimethoxyphenyl)acrylate；(2-acetyl-3-methoxyphenyl) (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1172141-24-0
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: FRLVCOYVGJHHQB-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-methoxyphenyl (E)-3,4-dimethoxycinnamate 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以65%的产率得到5-(3,4-dimethoxyphenyl)-3-hydroxy-1-(2-hydroxy-6-methoxyphenyl)penta-2,4-dien-1-one
  参考文献：
  名称：

  新型多羟基化 2,3-二芳基-9H-xanthen-9-ones 的高效合成

  摘要：

  已经通过两种不同的方法合成了大量羟基化的 2,3-二芳基-9H-xanthen-9-ones，从 3-bromo-2-methyl-4H-chromen-4-one 或 (E)- 3-bromo-2-styryl-4H-chromen-4-ones。前一种方法涉及 3-bromo-2-methyl-4H-chromen-4-one 和苯乙烯之间的 Heck 反应，导致 (E)-2-methyl-3-styryl-4H-chromen-4-ones; 这些与苯甲醛缩合得到 (E,E)-2,3-distyryl-4H-chromen-4-ones，这导致所需的 2,3-diaryl-9H-xanthen-9-ones 在 1,2 中回流,4-三氯苯。3-Bromo-2-styryl-4H-chromen-4-ones 是通过 3-bromo-2-methyl-4H-chromen-4-one 和苯甲醛之间的羟醛缩合获得的，或者通过

  DOI：

  10.1002/ejoc.200900026
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 、 1-(2-羟基-6-甲氧基苯基)乙基-1-酮 在 吡啶 、 三氯氧磷 作用下， 以90%的产率得到2-acetyl-3-methoxyphenyl (E)-3,4-dimethoxycinnamate
  参考文献：
  名称：

  1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors

  摘要：

  A series of (2E,4E)-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (3a-r) and (2Z,4E)-3-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (6a-l) were synthesized and evaluated in vitro as inhibitors of the two human Monoamine oxidase (hMAO) isoforms, MAO-A and MAO-B. Most of the compounds showed a selective MAO-B inhibitory activity in the nanomolar or low micromolar range. (2E,4E)-5-(4-Chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)penta-2,4-dien-1-one (3g) and (2E,4E)-5-(4-chlorophenyl)-1-(2,4-dihydroxyphenyl)penta-2,4-dien-1-one (3h) were the most potent hMAO-B inhibitors exhibiting IC50 of 4.51 nM and 1135 nM, respectively, coupled with high selectivity. Moreover, partial recovery of MAO-B activity was observed after repeated washing in the presence of isatin (reversible inhibitor) and compounds 3g and 3h suggesting a reversible inhibition of the enzyme. Molecular mechanics and quantum chemistry methods were used to elucidate the MAO recognition of the most active inhibitors 3g and 3h. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.006

文献信息

• Efficient Syntheses of New Polyhydroxylated 2,3-Diaryl-9<i>H</i>-xanthen-9-ones
  作者：Clementina M. M. Santos、Artur M. S. Silva、José A. S. Cavaleiro

  DOI：10.1002/ejoc.200900026

  日期：2009.6

  between 3-bromo-2-methyl-4H-chromen-4-one and benzaldehydes, or through Baker–Venkataraman rearrangements of 2-acetylphenyl cinnamates, followed by one-pot bromination/cyclisation with phenyltrimethylammonium tribromide. The 2,3-diaryl-9H-xanthene-9-ones were obtained in one-pot transformations involving Heck reactions between (E)-3-bromo-2-styryl-4H-chromen-4-ones and styrenes, followed by electrocyclisation

  已经通过两种不同的方法合成了大量羟基化的 2,3-二芳基-9H-xanthen-9-ones，从 3-bromo-2-methyl-4H-chromen-4-one 或 (E)- 3-bromo-2-styryl-4H-chromen-4-ones。前一种方法涉及 3-bromo-2-methyl-4H-chromen-4-one 和苯乙烯之间的 Heck 反应，导致 (E)-2-methyl-3-styryl-4H-chromen-4-ones; 这些与苯甲醛缩合得到 (E,E)-2,3-distyryl-4H-chromen-4-ones，这导致所需的 2,3-diaryl-9H-xanthen-9-ones 在 1,2 中回流,4-三氯苯。3-Bromo-2-styryl-4H-chromen-4-ones 是通过 3-bromo-2-methyl-4H-chromen-4-one 和苯甲醛之间的羟醛缩合获得的，或者通过
• 1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors
  作者：Nicoletta Desideri、Rossella Fioravanti、Luca Proietti Monaco、Mariangela Biava、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.ejmech.2012.11.006

  日期：2013.1

  A series of (2E,4E)-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (3a-r) and (2Z,4E)-3-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (6a-l) were synthesized and evaluated in vitro as inhibitors of the two human Monoamine oxidase (hMAO) isoforms, MAO-A and MAO-B. Most of the compounds showed a selective MAO-B inhibitory activity in the nanomolar or low micromolar range. (2E,4E)-5-(4-Chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)penta-2,4-dien-1-one (3g) and (2E,4E)-5-(4-chlorophenyl)-1-(2,4-dihydroxyphenyl)penta-2,4-dien-1-one (3h) were the most potent hMAO-B inhibitors exhibiting IC50 of 4.51 nM and 1135 nM, respectively, coupled with high selectivity. Moreover, partial recovery of MAO-B activity was observed after repeated washing in the presence of isatin (reversible inhibitor) and compounds 3g and 3h suggesting a reversible inhibition of the enzyme. Molecular mechanics and quantum chemistry methods were used to elucidate the MAO recognition of the most active inhibitors 3g and 3h. (C) 2012 Elsevier Masson SAS. All rights reserved.