2-(3,4,5-trimethoxybenzoyl)-1-phenylbutan-1,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,4,5-trimethoxybenzoyl)-1-phenylbutan-1,3-dione
• 英文别名: (1,3-Dioxo-1-phenylbutan-2-yl) 3,4,5-trimethoxybenzoate；(1,3-dioxo-1-phenylbutan-2-yl) 3,4,5-trimethoxybenzoate
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: MKLBTAAZRPXJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(3,4,5-trimethoxybenzoyl)-1-phenylbutan-1,3-dione 在 hexafluorophosphoric acid 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 8-hydroxy-4-(3,4,5-trimethoxybenzoyloxy)-5-phenyl-2-(4-(N,N-dimethylamino)phenyl)-1,6-dioxaphenalenium hexafluorophosphate
  参考文献：
  名称：

  Aged red wine pigments as a source of inspiration for organic synthesis—the cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores

  摘要：

  Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4 -> 8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.058
• 作为产物：
  描述：

  1-苯基-1,3-丁二酮 在 N-氯代丁二酰亚胺 、 sodium hydride 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 2-(3,4,5-trimethoxybenzoyl)-1-phenylbutan-1,3-dione
  参考文献：
  名称：

  Aged red wine pigments as a source of inspiration for organic synthesis—the cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores

  摘要：

  Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4 -> 8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.058

文献信息

• Aged red wine pigments as a source of inspiration for organic synthesis—the cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores
  作者：Stefan Chassaing、Géraldine Isorez-Mahler、Marie Kueny-Stotz、Raymond Brouillard

  DOI：10.1016/j.tet.2014.10.058

  日期：2015.5

  Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4 -> 8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration. (C) 2014 Elsevier Ltd. All rights reserved.