(Z)-1,2-di(2-bromopyridin-3-yl)ethene | 942267-02-9

• 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: (Z)-1,2-di(2-bromopyridin-3-yl)ethene
• 英文别名: (Z)-1,2-di(2-bromo-3-pyridyl)ethene；1,2-bis(2-bromopyridin-3-yl)ethane；2-bromo-3-[(Z)-2-(2-bromopyridin-3-yl)ethenyl]pyridine
• CAS: 942267-02-9
• 化学式: C₁₂H₈Br₂N₂
• 分子量: 340.017
• InChiKey: HTWYMZHCZJTNJE-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1,2-di(2-bromopyridin-3-yl)ethene 在 铜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以67%的产率得到1,10-菲罗啉
  参考文献：
  名称：

  A new approach to the 1,10-phenanthroline core

  摘要：

  A protocol for the synthesis of substituted 1,10-phenanthrolines is reported. The phenanthroline scaffold has been obtained constructing the central cycle starting from two pyridine rings. The method is hinged upon the intramolecular coupling of eiv-1,2-di(2-bromo-3-pyridyl)ethenes that are in turn obtained from the Wittig reaction of 2-bromonicotinalclehydes with phosphonium salts prepared from 2-bromo-3-(bromomethyl)pyridines. Yields up to 75% have been obtained. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.073
• 作为产物：
  描述：

  2-bromo-3-(2-(2-bromopyridin-3-yl)ethynyl)pyridine 在 Pd-BaSO₄ 氢气 作用下， 以 苯 为溶剂， 反应 24.0h， 以51%的产率得到(Z)-1,2-di(2-bromopyridin-3-yl)ethene
  参考文献：
  名称：

  Alternative approaches to (Z)-1,2-bis(2-bromopyridin-3-yl)ethenes, key intermediates in the synthesis of the 1,10-phenanthroline core

  摘要：

  A study on the synthesis of (Z)-1,2-bis(2-bromopyridin-3-yl)ethenes, key intermediates in the preparation of 1,10-phenanthrolines, based on selective Sonogashira and Suzuki-Miyaura cross-coupling reactions has been carried out. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.112

文献信息

• 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.
• Alternative approaches to (Z)-1,2-bis(2-bromopyridin-3-yl)ethenes, key intermediates in the synthesis of the 1,10-phenanthroline core
  作者：Giorgio Chelucci、Salvatore Baldino、Gerard A. Pinna、Barbara Sechi

  DOI：10.1016/j.tetlet.2008.02.112

  日期：2008.4

  A study on the synthesis of (Z)-1,2-bis(2-bromopyridin-3-yl)ethenes, key intermediates in the preparation of 1,10-phenanthrolines, based on selective Sonogashira and Suzuki-Miyaura cross-coupling reactions has been carried out. (C) 2008 Elsevier Ltd. All rights reserved.
• A new approach to the 1,10-phenanthroline core
  作者：Giorgio Chelucci、Daniele Addis、Salvatore Baldino

  DOI：10.1016/j.tetlet.2007.03.073

  日期：2007.5

  A protocol for the synthesis of substituted 1,10-phenanthrolines is reported. The phenanthroline scaffold has been obtained constructing the central cycle starting from two pyridine rings. The method is hinged upon the intramolecular coupling of eiv-1,2-di(2-bromo-3-pyridyl)ethenes that are in turn obtained from the Wittig reaction of 2-bromonicotinalclehydes with phosphonium salts prepared from 2-bromo-3-(bromomethyl)pyridines. Yields up to 75% have been obtained. (c) 2007 Elsevier Ltd. All rights reserved.