6-((E)-4-stilbenyl)hexa-3,5-diyn-1-ol

• 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: 6-((E)-4-stilbenyl)hexa-3,5-diyn-1-ol
• 英文别名: 6-[4-[(E)-2-phenylethenyl]phenyl]hexa-3,5-diyn-1-ol
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: BHDNGJPAXSJEDM-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-丁炔-1-醇 、 2-((E)-4-stilbenyl)-1,1-dibromoethene 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以62%的产率得到6-((E)-4-stilbenyl)hexa-3,5-diyn-1-ol
  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

• 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.