2,6-bis(bromoethynyl)anisole | 1366768-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-bis(bromoethynyl)anisole
• 英文别名: 1,3-Bis(2-bromoethynyl)-2-methoxybenzene；1,3-bis(2-bromoethynyl)-2-methoxybenzene
• CAS: 1366768-04-8
• 化学式: C₁₁H₆Br₂O
• 分子量: 313.976
• InChiKey: RJVUVEBOUOORIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  苯酚 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 双氧水 、 碘 、 potassium carbonate 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 22.33h， 生成 2,6-bis(bromoethynyl)anisole
  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

• 1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase
  作者：Berin A. Boughton、Lilian Hor、Juliet A. Gerrard、Craig A. Hutton

  DOI：10.1016/j.bmc.2012.01.045

  日期：2012.4

  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.