(Z)-3,4-diphenyl-2-(2-thienyl)dec-3-en-5-yn-2-ol | 864943-42-0

• 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: (Z)-3,4-diphenyl-2-(2-thienyl)dec-3-en-5-yn-2-ol
• 英文别名: (Z)-3,4-diphenyl-2-thiophen-2-yldec-3-en-5-yn-2-ol
• CAS: 864943-42-0
• 化学式: C₂₆H₂₆OS
• 分子量: 386.558
• InChiKey: WDOWZQZMYBIIEJ-WJTDDFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3,4-diphenyl-2-(2-thienyl)dec-3-en-5-yn-2-ol 在 sodium methyl carbonate 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到(Z)-5-(1-iodopentylidene)-2-methyl-3,4-diphenyl-2-(2-thienyl)-2,5-dihydrofuran
  参考文献：
  名称：

  A Facile Zr-Mediated Approach to (Z)-Enynols and Its Application to Regio- and Stereoselective Synthesis of Fully Substituted Dihydrofurans

  摘要：

  [GRAPHICS]Efficient synthetic approaches to stereodefined (Z)-enynols have been developed through zirconium-mediated cross-coupling reactions of three different components involving alkyne, ketone, and alkynyl bromide in a one-pot procedure. The subsequent electrophilic cyclization of a wide variety of (Z)-enynols affords fully substituted (Z)-5-(1-iodoylidene)2,5-dihydrofurans with high regio- and stereoselectivity under mild reaction conditions.

  DOI：

  10.1021/jo050966z
• 作为产物：
  描述：

  2-乙酰基噻吩 、 1-bromohexyne 、 二苯基乙炔 在 Cp2ZrEt2 、 copper(l) chloride 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以57%的产率得到(Z)-3,4-diphenyl-2-(2-thienyl)dec-3-en-5-yn-2-ol
  参考文献：
  名称：

  A Facile Zr-Mediated Approach to (Z)-Enynols and Its Application to Regio- and Stereoselective Synthesis of Fully Substituted Dihydrofurans

  摘要：

  [GRAPHICS]Efficient synthetic approaches to stereodefined (Z)-enynols have been developed through zirconium-mediated cross-coupling reactions of three different components involving alkyne, ketone, and alkynyl bromide in a one-pot procedure. The subsequent electrophilic cyclization of a wide variety of (Z)-enynols affords fully substituted (Z)-5-(1-iodoylidene)2,5-dihydrofurans with high regio- and stereoselectivity under mild reaction conditions.

  DOI：

  10.1021/jo050966z

文献信息

• Cleavage of a Carbon−Carbon Triple Bond via Gold-Catalyzed Cascade Cyclization/Oxidative Cleavage Reactions of (<i>Z</i>)-Enynols with Molecular Oxygen
  作者：Yuanhong Liu、Feijie Song、Shenghai Guo

  DOI：10.1021/ja062610q

  日期：2006.9.1

  A highly efficient carbon-carbon triple bond cleavage reaction of (Z)-enynols was developed, which offered a new route to highly substituted butenolides. The methodology is realized by a tandem reaction using a single gold(I) catalyst, which could catalyze different reactions of cyclization/oxidative cleavage in the same vessel.

  开发了（Z）-烯醇的高效碳碳三键裂解反应，为高度取代的丁烯内酯提供了一条新途径。该方法是通过使用单一金（I）催化剂的串联反应实现的，该催化剂可以在同一容器中催化不同的环化/氧化裂解反应。
• A Facile Zr-Mediated Approach to (<i>Z</i>)-Enynols and Its Application to Regio- and Stereoselective Synthesis of Fully Substituted Dihydrofurans
  作者：Yuanhong Liu、Feijie Song、Liqing Cong

  DOI：10.1021/jo050966z

  日期：2005.8.1

  [GRAPHICS]Efficient synthetic approaches to stereodefined (Z)-enynols have been developed through zirconium-mediated cross-coupling reactions of three different components involving alkyne, ketone, and alkynyl bromide in a one-pot procedure. The subsequent electrophilic cyclization of a wide variety of (Z)-enynols affords fully substituted (Z)-5-(1-iodoylidene)2,5-dihydrofurans with high regio- and stereoselectivity under mild reaction conditions.