1-bromo-2-((E)-4-stilbenyl)ethyne | 386213-51-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-bromo-2-((E)-4-stilbenyl)ethyne
• 英文别名: 1-(2-bromoethynyl)-4-[(E)-2-phenylethenyl]benzene
• CAS: 386213-51-0
• 化学式: C₁₆H₁₁Br
• 分子量: 283.167
• InChiKey: KJKUSAZTMHZZSB-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-bromo-2-((E)-4-stilbenyl)ethyne 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 2.0h， 以40%的产率得到1,4-bis((E)-4-stilbenyl)buta-1,3-diyne
  参考文献：
  名称：

  Synthesis of 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene from the Sonogashira reactions of 2-aryl-1,1-dibromoethene

  摘要：

  Both 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene were produced from the Sonogasbira reactions of 2-aryl-1,1-dibromoethene with 1-alkyne. The ratio of the products varied according to the reaction conditions. The coupling reactions in benzene afforded the 2-aryl-1,1-dialkynylethene as a major product and no 1-aryl-1,3-diyne was isolated. The 1-aryl-1,3-diyne could be obtained in DMF in acceptable yields. When amines were used as a reaction solvent, the coupling reaction gave the 2-aryl-1, 1-dialkynylethene (20%) and the conjugated enyne (68%) in diisopropylamine, whereas only the 1-aryl-1,3-diyne was isolated in piperidine in 56% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00829-8
• 作为产物：
  描述：

  4-二苯乙烯甲醛 在 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-bromo-2-((E)-4-stilbenyl)ethyne
  参考文献：
  名称：

  Synthesis of 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene from the Sonogashira reactions of 2-aryl-1,1-dibromoethene

  摘要：

  Both 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene were produced from the Sonogasbira reactions of 2-aryl-1,1-dibromoethene with 1-alkyne. The ratio of the products varied according to the reaction conditions. The coupling reactions in benzene afforded the 2-aryl-1,1-dialkynylethene as a major product and no 1-aryl-1,3-diyne was isolated. The 1-aryl-1,3-diyne could be obtained in DMF in acceptable yields. When amines were used as a reaction solvent, the coupling reaction gave the 2-aryl-1, 1-dialkynylethene (20%) and the conjugated enyne (68%) in diisopropylamine, whereas only the 1-aryl-1,3-diyne was isolated in piperidine in 56% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00829-8

文献信息

• De Novo Synthesis of 1,4-Dihydropyridines and Pyridines
  作者：Wafa Gati、Mohamed M. Rammah、Mohamed B. Rammah、François Couty、Gwilherm Evano

  DOI：10.1021/ja303002a

  日期：2012.6.6

  An efficient and general method for the synthesis of 1,4-dihydropyridines and pyridines based on a lithiation/isomerization/intramolecular carbolithiation sequence is reported. This procedure provides an efficient, divergent, and straightforward entry to a wide range of polysubstituted dihydropyridines and pyridines starting from readily available N-allyl-ynamides.
• Synthesis of 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene from the Sonogashira reactions of 2-aryl-1,1-dibromoethene
  作者：Hee Bong Lee、Dal Ho Huh、Joon Seok Oh、Gwan-Hong Min、Byung Hyun Kim、Dong Hwal Lee、Jae Kwang Hwang、Young Gyu Kim

  DOI：10.1016/s0040-4020(01)00829-8

  日期：2001.9

  Both 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene were produced from the Sonogasbira reactions of 2-aryl-1,1-dibromoethene with 1-alkyne. The ratio of the products varied according to the reaction conditions. The coupling reactions in benzene afforded the 2-aryl-1,1-dialkynylethene as a major product and no 1-aryl-1,3-diyne was isolated. The 1-aryl-1,3-diyne could be obtained in DMF in acceptable yields. When amines were used as a reaction solvent, the coupling reaction gave the 2-aryl-1, 1-dialkynylethene (20%) and the conjugated enyne (68%) in diisopropylamine, whereas only the 1-aryl-1,3-diyne was isolated in piperidine in 56% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.