5-(2-羟基苯甲酰基)-2-甲基-1,3-苯二甲酸二乙酯 | 57443-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(2-羟基苯甲酰基)-2-甲基-1,3-苯二甲酸二乙酯
• 英文名称: diethyl 5-(2-hydroxybenzoyl)-2-methyl-1,3-benzenedicarboxylate
• 英文别名: diethyl 5-(2-hydroxybenzoyl)-2-methylisophthalate；Diethyl 5-(2-hydroxybenzoyl)-2-methylbenzene-1,3-dicarboxylate
• CAS: 57443-90-0
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: WQFZHVDRCZHZBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 色酮-3-甲醛 在 三乙烯二胺 、 十六烷基三甲基溴化铵 作用下， 以 水 为溶剂， 反应 1.5h， 以82%的产率得到5-(2-羟基苯甲酰基)-2-甲基-1,3-苯二甲酸二乙酯
  参考文献：
  名称：

  A Mild and Efficient Route to 3-Vinylchromones in Aqueous Micellar Media

  摘要：

  A simple, mild, and ecofriendly method has been developed for the synthesis of 3-vinylchromones from 4-oxo-4H-1-benzopyran-3-carboxaldehyde (3-formylchromone) by simple Knoevenagel condensation with various active methylene compounds (AMC) in aqueous micellar media in the presence of catalytic amounts of cetyl trimethylammonium bromide (CTAB) and 1,4-diazabicyclo[2.2.2]octane (DABCO). In the case of malonic acid as AMC, the reaction resulted in formation of only Doebner decarboxylated products under the standard reaction condition. It has been also observed that 3-formylchromone derivatives primarily undergo tandem Knoevenagel and Michael reactions in the presence of >2 equiv. of ethyl acetoacetate to produce benzophenone derivatives, by opening of pyran ring, as the sole product in good yields.

  DOI：

  10.1080/00397911.2015.1084008

文献信息

• Domino Reaction to Functionalized 2-Hydroxybenzophenones from Electron-Deficient Chromones and 1,3-Dicarbonyl Compounds
  作者：Hong Chen、Fuchun Xie、Jian Gong、Youhong Hu

  DOI：10.1021/jo201384f

  日期：2011.10.21

  A base-promoted one-pot tandem reaction sequence has been developed to transform electron-deficient chromone-fused dienes 1 and 1,3-dicarbonyl compounds 2 to functionalized 2-hydroxybenzophenones 3 under mild conditions. This domino process, which involves multiple reactions, including Michael addition/cyclization/elimination, serves as an efficient, economic, and eco-friendly method for the construction

  已经开发了碱促进的一锅串联反应序列，以在温和条件下将缺电子的色酮稠合二烯1和1,3-二羰基化合物2转变为功能化的2-羟基二苯甲酮3。这种多米诺骨牌工艺涉及多个反应，包括迈克尔加成/环化/消除反应，是一种高效，经济，环保的方法，可用于构建没有过渡金属催化剂和惰性气氛的各种2-羟基二苯甲酮支架。