Diethyl ((2-bromopyridin-3-yl)methyl)phosphonate | 1246557-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Diethyl ((2-bromopyridin-3-yl)methyl)phosphonate
• 英文别名: 2-bromo-3-(diethoxyphosphorylmethyl)pyridine
• CAS: 1246557-06-1
• 化学式: C₁₀H₁₅BrNO₃P
• 分子量: 308.112
• InChiKey: CTLNDNXVQOTOCC-UHFFFAOYSA-N

物化性质

• 沸点：
  398.9±32.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diethyl ((2-bromopyridin-3-yl)methyl)phosphonate 、 2-溴-3-吡啶甲醛 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以63%的产率得到(E)-1,2-di(2-bromopyridin-3-yl)ethene
  参考文献：
  名称：

  Stereoselective synthesis of 5,6-disubstituted 5,6-dihydro-1,10-phenanthrolines and a rare example of axially constrained 2,2′-bipyridines

  摘要：

  The stereoselective synthesis of 5,6-disubstituted 5,6-dihydro-1,10-phenanthrolines and (5S,6S)-5,6dihydroxy-5,6-dihydro-1,10-phenanthroline cyclic o-xylylene diether, a rare example of an axially constrained 2,2'-bipyridine is reported. The strategy to obtain such compounds is based on two highly efficient reactions, the Sharpless asymmetric dihydroxylation and the Ullmann intramolecular coupling. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.021
• 作为产物：
  描述：

  2-溴-3-(溴甲基)吡啶 、 亚磷酸三乙酯 反应 0.5h， 以70%的产率得到Diethyl ((2-bromopyridin-3-yl)methyl)phosphonate
  参考文献：
  名称：

  Stereoselective synthesis of 5,6-disubstituted 5,6-dihydro-1,10-phenanthrolines and a rare example of axially constrained 2,2′-bipyridines

  摘要：

  The stereoselective synthesis of 5,6-disubstituted 5,6-dihydro-1,10-phenanthrolines and (5S,6S)-5,6dihydroxy-5,6-dihydro-1,10-phenanthroline cyclic o-xylylene diether, a rare example of an axially constrained 2,2'-bipyridine is reported. The strategy to obtain such compounds is based on two highly efficient reactions, the Sharpless asymmetric dihydroxylation and the Ullmann intramolecular coupling. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.021

文献信息

• Development of LpxH Inhibitors Chelating the Active Site Dimanganese Metal Cluster of LpxH
  作者：Seung‐Hwa Kwak、C. Skyler Cochrane、Jae Cho、Patrick A. Dome、Amanda F. Ennis、Jea Hyun Kim、Pei Zhou、Jiyong Hong

  DOI：10.1002/cmdc.202300023

  日期：2023.6

  In the lipid A biosynthetic pathway, the enzyme LpxH is a promising antibiotic drug target. In this work, several sulfonyl piperazine LpxH inhibitors were designed and synthesized. Among them, JH-LPH-50 shows improved activity against LpxH by chelating the dimanganese cluster in the active site of LpxH.

  在脂质A生物合成途径中，酶LpxH是一个有前途的抗生素药物靶点。在这项工作中，设计并合成了几种磺酰哌嗪LpxH抑制剂。其中，JH-LPH-50通过螯合LpxH活性位点的二锰簇，显示出针对LpxH的更高活性。
• Stereoselective synthesis of 5,6-disubstituted 5,6-dihydro-1,10-phenanthrolines and a rare example of axially constrained 2,2′-bipyridines
  作者：Giorgio Chelucci、Claudia Sanfilippo

  DOI：10.1016/j.tetasy.2010.06.021

  日期：2010.8

  The stereoselective synthesis of 5,6-disubstituted 5,6-dihydro-1,10-phenanthrolines and (5S,6S)-5,6dihydroxy-5,6-dihydro-1,10-phenanthroline cyclic o-xylylene diether, a rare example of an axially constrained 2,2'-bipyridine is reported. The strategy to obtain such compounds is based on two highly efficient reactions, the Sharpless asymmetric dihydroxylation and the Ullmann intramolecular coupling. (C) 2010 Elsevier Ltd. All rights reserved.