4-(2-bromo-2-phenylvinyl)pyridine | 174844-93-0

• 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: 4-(2-bromo-2-phenylvinyl)pyridine
• 英文别名: 4-(β-bromo-styryl)-pyridine；4-(β-Brom-styryl)-pyridin；4-[(Z)-2-bromo-2-phenylethenyl]pyridine
• CAS: 174844-93-0
• 化学式: C₁₃H₁₀BrN
• 分子量: 260.133
• InChiKey: PJGLJEPVENKAKD-RAXLEYEMSA-N

物化性质

• 沸点：
  344.9±30.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2-bromo-2-phenylvinyl)pyridine 在 氢氧化钾 作用下， 生成 4-(苯基乙炔)吡啶
  参考文献：
  名称：

  α-Aminophenacylpyridines and Quinolines¹

  摘要：

  DOI：

  10.1021/ja01192a009
• 作为产物：
  描述：

  4-(苯基乙炔)吡啶 在 氢溴酸 作用下， 以 氯仿 为溶剂， 反应 192.0h， 以26%的产率得到4-(2-bromo-2-phenylvinyl)pyridine
  参考文献：
  名称：

  Convenient Synthesis and Cytokinin Activity of β-Substituted 4-Styrylpyridines, the Simplest Cytokinin Analogs with a Moderate Cell Division-Promoting Activity

  摘要：

  Designed synthesis of Z- and E-isomers of beta-substituted 4-styrylpyridines as cytokinin analogs was conveniently achieved by nucleophilic and electrophilic addition of ethanol, methyl mercaptan, and hydrogen halides (HCl, HBr, and HI) to 4-(phenylethynyl)pyridine prepared by palladium-catalyzed coupling. They easily underwent E-Z photoisomerization under monochromatic UV light or sunlight. A tobacco callus assay revealed that the Z-isomers were more active than their E-isomers and that the Z-ethoxy derivative, which showed the highest activity among the P-substituted 4-styrylpyridines, was one-fifth as potent as kinetin. The Z-ethoxy derivative also promoted betacyanin biosynthesis of Amaranthus seedlings at 4-100 mu M.

  DOI：

  10.1021/jf9502313

文献信息

• 一种芳香乙烯基溴衍生物的制备方法
  申请人：哈尔滨工业大学（深圳）（哈尔滨工业大学深圳 科技创新研究院）

  公开号：CN111675650B

  公开（公告）日：2021-09-03

  一种芳香乙烯基溴衍生物的制备方法，本发明涉及一种芳香乙烯基溴衍生物的制备方法。本发明的目的是为了解决现有方法合成芳香乙烯基溴衍生物反应条件苛刻、底物兼容性差且污染环境的问题，本发明室温下，在氮气气氛下，将炔烃衍生物、溴代芳香环类化合物和催化剂溶解在有机溶剂中，进行光照反应，待反应结束后，旋蒸溶剂，提纯，即完成；本发明解决了现有芳香乙烯基溴衍生物合成需要有毒有害物质激发和过渡金属催化体系导致的产率低、方法环保性差、底物兼容性差的问题，本发明应用于有机合成领域。
• α-Aminophenacylpyridines and Quinolines¹
  作者：James M. Smith、Hugh W. Stewart、Barbara Roth、Elmore H. Northey

  DOI：10.1021/ja01192a009

  日期：1948.12
• Convenient Synthesis and Cytokinin Activity of β-Substituted 4-Styrylpyridines, the Simplest Cytokinin Analogs with a Moderate Cell Division-Promoting Activity
  作者：Shiro Nishikawa、Masakazu Sato、Hisaki Kojima、Chi-e Suzuki、Nobuko Yamada、Minoru Inagaki、Naoki Kashimura、Hiroshi Mizuno

  DOI：10.1021/jf9502313

  日期：1996.1.1

  Designed synthesis of Z- and E-isomers of beta-substituted 4-styrylpyridines as cytokinin analogs was conveniently achieved by nucleophilic and electrophilic addition of ethanol, methyl mercaptan, and hydrogen halides (HCl, HBr, and HI) to 4-(phenylethynyl)pyridine prepared by palladium-catalyzed coupling. They easily underwent E-Z photoisomerization under monochromatic UV light or sunlight. A tobacco callus assay revealed that the Z-isomers were more active than their E-isomers and that the Z-ethoxy derivative, which showed the highest activity among the P-substituted 4-styrylpyridines, was one-fifth as potent as kinetin. The Z-ethoxy derivative also promoted betacyanin biosynthesis of Amaranthus seedlings at 4-100 mu M.