dimethyl 2,2'-(2-methoxy-1,3-phenylene)bis(2-oxoacetate) | 1366768-05-9

• 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: dimethyl 2,2'-(2-methoxy-1,3-phenylene)bis(2-oxoacetate)
• CAS: 1366768-05-9
• 化学式: C₁₃H₁₂O₇
• 分子量: 280.234
• InChiKey: PKXQTJBZEUMOAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2'-(2-methoxy-1,3-phenylene)bis(2-oxoacetate) 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到dimethyl 2,2'-(2-hydroxy-1,3-phenylene)bis(2-oxoacetate)
  参考文献：
  名称：

  1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase

  摘要：

  Dihydrodipicolinate synthase is a key enzyme in the lysine biosynthesis pathway that catalyzes the condensation of pyruvate and aspartate semi-aldehyde. A series of phenolic ketoacid derivatives that mimic the proposed enzymatic intermediate were designed as potential inhibitors of this enzyme and were synthesized from simple precursors. The ketoacid derivatives were shown to act as slow and slow-tight binding inhibitors. Mass spectrometric experiments provided further evidence to support the proposed model of inhibition, demonstrating either an encounter complex or a condensation product for the slow and slow-tight binding inhibitors, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.045
• 作为产物：
  描述：

  甲醇 、 2,6-bis(bromoethynyl)anisole 在 potassium permanganate 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 以99%的产率得到dimethyl 2,2'-(2-methoxy-1,3-phenylene)bis(2-oxoacetate)
  参考文献：
  名称：

  1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase

  摘要：

  Dihydrodipicolinate synthase is a key enzyme in the lysine biosynthesis pathway that catalyzes the condensation of pyruvate and aspartate semi-aldehyde. A series of phenolic ketoacid derivatives that mimic the proposed enzymatic intermediate were designed as potential inhibitors of this enzyme and were synthesized from simple precursors. The ketoacid derivatives were shown to act as slow and slow-tight binding inhibitors. Mass spectrometric experiments provided further evidence to support the proposed model of inhibition, demonstrating either an encounter complex or a condensation product for the slow and slow-tight binding inhibitors, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.045

文献信息

• Copper catalyzed photoredox synthesis of α-keto esters, quinoxaline, and naphthoquinone: controlled oxidation of terminal alkynes to glyoxals
  作者：Deb Kumar Das、V. Kishore Kumar Pampana、Kuo Chu Hwang

  DOI：10.1039/c8sc03447h

  日期：——

  catalyzed controlled oxidation of terminal CC alkynes to α-keto esters and quinoxalines via formation of phenylglyoxals as stable intermediates, under mild conditions by using molecular O2 as a sustainable oxidant. The current copper catalysed photoredox method is simple, highly functional group compatible with a broad range of electron rich and electron poor aromatic alkynes as well as aliphatic alcohols

  在此，我们报道了一种在温和条件下使用分子 O 2通过形成苯基乙二醛作为稳定的中间体，在可见光诱导的铜催化下，末端 C C 炔烃可控氧化为 α-酮酯和喹喔啉的方法。作为一种可持续的氧化剂。目前的铜催化光氧化还原方法简单、官能团高，与广泛的富电子和贫电子芳烃以及脂肪醇（1°、2°和3°醇）相容，为制备α-酮酯（43 个例子）、喹喔啉和萘醌的产率高于文献报道的热工艺。此外，该产品的合成效用已在两种生物活性分子的合成中得到证明，即大肠杆菌DHPS 抑制剂和 CFTR 活化剂，使用当前的光氧化还原过程。此外，我们将该方法应用于杂环化合物（喹喔啉，一种 FLT3 抑制剂）的一锅合成，方法是用邻苯二胺。也可以分离中间体苯乙二醛并进一步与内部炔烃反应以形成萘醌。这个过程可以很容易地放大到克级。