3-(p-nitrobenzoyloxy)-4-(2,4,5-trimethoxyphenyl)-2-butanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(p-nitrobenzoyloxy)-4-(2,4,5-trimethoxyphenyl)-2-butanone
• 英文别名: [3-Oxo-1-(2,4,5-trimethoxyphenyl)butan-2-yl] 4-nitrobenzoate
• 化学式: C₂₀H₂₁NO₈
• 分子量: 403.389
• InChiKey: JZGLCEDOYLTILR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 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：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(p-nitrobenzoyloxy)-4-(2,4,5-trimethoxyphenyl)-2-butanone 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以92%的产率得到3-hydroxy-4-(2,4,5-trimethoxyphenyl)butan-2-one
  参考文献：
  名称：

  Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

  摘要：

  Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.010
• 作为产物：
  描述：

  1,2,4-三甲氧基苯 、 3-(p-nitrobenzoyloxy)-3-buten-2-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到3-(p-nitrobenzoyloxy)-4-(2,4,5-trimethoxyphenyl)-2-butanone
  参考文献：
  名称：

  Friedel–Crafts Reaction of Activated Benzene Rings with Captodative and Electron‐Deficient Alkenes. A One‐Step Synthesis of the Natural Product Methyl 3‐(2,4,5‐Trimethoxyphenyl)propionate

  摘要：

  Electrophilic aromatic substitution of activated benzenes with the captodative olefin 1-acetylvinyl-1-p-nitrobenzoate (9), and with the electron-deficient alkenes methyl acrylate (8a), methylvinylketone (8b), and acrolein (8c) were evaluated under Lewis acid catalysis. Olefin 9 proved to be much more reactive than alkenes 8a-8c. We also describe a one-step synthesis of the antifungal and larvicidal natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate (6), by reaction of 1,2,4-trimethoxybenzene with 8a under microwave irradiation.

  DOI：

  10.1081/scc-200026193

文献信息

• Friedel–Crafts Reaction of Activated Benzene Rings with Captodative and Electron‐Deficient Alkenes. A One‐Step Synthesis of the Natural Product Methyl 3‐(2,4,5‐Trimethoxyphenyl)propionate
  作者：Raúl Aguilar、Adriana Benavides、Joaquín Tamariz

  DOI：10.1081/scc-200026193

  日期：2004.1

  Electrophilic aromatic substitution of activated benzenes with the captodative olefin 1-acetylvinyl-1-p-nitrobenzoate (9), and with the electron-deficient alkenes methyl acrylate (8a), methylvinylketone (8b), and acrolein (8c) were evaluated under Lewis acid catalysis. Olefin 9 proved to be much more reactive than alkenes 8a-8c. We also describe a one-step synthesis of the antifungal and larvicidal natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate (6), by reaction of 1,2,4-trimethoxybenzene with 8a under microwave irradiation.
• Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products
  作者：Daniel Zárate-Zárate、Raúl Aguilar、R. Israel Hernández-Benitez、Ehecatl M. Labarrios、Francisco Delgado、Joaquín Tamariz

  DOI：10.1016/j.tet.2015.07.010

  日期：2015.9

  Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.