(E)-2-benzylidene-4-(cyclohexen-1-yl)-1-phenylbut-3-yn-1-ol | 1311273-16-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-benzylidene-4-(cyclohexen-1-yl)-1-phenylbut-3-yn-1-ol
• 英文别名: (2E)-2-benzylidene-4-(cyclohexen-1-yl)-1-phenylbut-3-yn-1-ol
• CAS: 1311273-16-1
• 化学式: C₂₃H₂₂O
• 分子量: 314.427
• InChiKey: LSWPAFIXODPGGF-RELWKKBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-甲基呋喃 、 (E)-2-benzylidene-4-(cyclohexen-1-yl)-1-phenylbut-3-yn-1-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到(Z)-2-(2-benzylidene-4-cyclohexen-1-yl-1-phenylbut-3-ynyl)-5-methylfuran
  参考文献：
  名称：

  Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes

  摘要：

  A new approach to functionalized fulvenes with an enone or enal moiety has been developed through gold-catalyzed intramolecular cycloisomerization of furan/ynes with a two-carbon tether in between the furan and the triple bond. The reaction proceeds with complete regioselectivity via a 6-endo-cyclization and high stereoselectivity. Moreover, the E- or Z-stereochemistry of the double bond in fulvene products can be easily controlled by performing the reaction in different solvents.

  DOI：

  10.1021/jo2004023
• 作为产物：
  描述：

  (2Z)-2-bromo-3-phenyl-2-propenal 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (E)-2-benzylidene-4-(cyclohexen-1-yl)-1-phenylbut-3-yn-1-ol
  参考文献：
  名称：

  Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes

  摘要：

  A new approach to functionalized fulvenes with an enone or enal moiety has been developed through gold-catalyzed intramolecular cycloisomerization of furan/ynes with a two-carbon tether in between the furan and the triple bond. The reaction proceeds with complete regioselectivity via a 6-endo-cyclization and high stereoselectivity. Moreover, the E- or Z-stereochemistry of the double bond in fulvene products can be easily controlled by performing the reaction in different solvents.

  DOI：

  10.1021/jo2004023

文献信息

• Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes
  作者：Yifeng Chen、Yuanhong Liu

  DOI：10.1021/jo2004023

  日期：2011.7.1

  A new approach to functionalized fulvenes with an enone or enal moiety has been developed through gold-catalyzed intramolecular cycloisomerization of furan/ynes with a two-carbon tether in between the furan and the triple bond. The reaction proceeds with complete regioselectivity via a 6-endo-cyclization and high stereoselectivity. Moreover, the E- or Z-stereochemistry of the double bond in fulvene products can be easily controlled by performing the reaction in different solvents.