( E)-2-benzylidene-4-(1-cyclohexenyl)but-3-ynal | 1311273-09-2

• 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: ( E)-2-benzylidene-4-(1-cyclohexenyl)but-3-ynal
• 英文别名: (E)-2-benzylidene-4-(cyclohexen-1-yl)but-3-ynal
• CAS: 1311273-09-2
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: JGENSTLRZOXSCC-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  ( E)-2-benzylidene-4-(1-cyclohexenyl)but-3-ynal 在 silver hexafluoroantimonate 、 三苯基膦氯金 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Efficient AgOTf or Ph3PAuCl–AgSbF6 catalyzed cyclization of 1-hydroxy-2-alkynylallylphosphonates/2-alkynylallyl alcohols to 2-furylphosphonates/2,3,5-trisubstituted furans

  摘要：

  The reaction of 1-hydroxy-2-alkynylallylphosphonates, synthesized by the addition of the corresponding phosphites to 2-alkynylcinnamaldehydes, under AgOTf or Ph3PAuCl-AgSbF6 catalyzed cycloisomerization afforded 2-furylphosphonates in good to excellent yields. These cyclization reactions were compared with those of 2-alkynylallyl alcohols that led to multisubstituted furans. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.04.060
• 作为产物：
  描述：

  1-乙炔基环己烷 、 (Z)-2-iodo-3-phenylacrylaldehyde 在 copper(l) iodide 、 二异丙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 ( E)-2-benzylidene-4-(1-cyclohexenyl)but-3-ynal
  参考文献：
  名称：

  Efficient AgOTf or Ph3PAuCl–AgSbF6 catalyzed cyclization of 1-hydroxy-2-alkynylallylphosphonates/2-alkynylallyl alcohols to 2-furylphosphonates/2,3,5-trisubstituted furans

  摘要：

  The reaction of 1-hydroxy-2-alkynylallylphosphonates, synthesized by the addition of the corresponding phosphites to 2-alkynylcinnamaldehydes, under AgOTf or Ph3PAuCl-AgSbF6 catalyzed cycloisomerization afforded 2-furylphosphonates in good to excellent yields. These cyclization reactions were compared with those of 2-alkynylallyl alcohols that led to multisubstituted furans. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.04.060

文献信息

• One-Pot Synthesis of Indole-Fused Scaffolds via Gold-Catalyzed Tandem Annulation Reactions of 1,2-Bis(alkynyl)-2-en-1-ones with Indoles
  作者：Xin Xie、Xiangwei Du、Yifeng Chen、Yuanhong Liu

  DOI：10.1021/jo2017668

  日期：2011.11.4

  The gold-catalyzed tandem cyclization of 1,2-bis(alkynyl)-2-en-1-ones with indoles offers an efficient and straightforward route to indole-fused polycyclic systems. The process is realized through a cascade carbonyl-yne cyclization/Friedel–Crafts/indole-yne cyclization sequence catalyzed by a single-pot catalyst of gold.

  1,2-双（炔基）-2-en-1-one与吲哚的金催化串联环化为吲哚稠合的多环体系提供了一条有效而直接的途径。该过程是通过单罐金催化剂催化的羰基-炔级联/ Friedel-Crafts /吲哚-炔级联反应来实现的。
• 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.