(Z)-2,3,4,6-tetraphenylhex-3-en-5-yn-2-ol | 864943-35-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (Z)-2,3,4,6-tetraphenylhex-3-en-5-yn-2-ol
• CAS: 864943-35-1
• 化学式: C₃₀H₂₄O
• 分子量: 400.52
• InChiKey: HAEJGPYMRSIYCE-ZQHSETAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (Z)-2,3,4,6-tetraphenylhex-3-en-5-yn-2-ol 在 tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以84%的产率得到5-methyl-3,4,5-triphenyl-5H-furan-2-one
  参考文献：
  名称：

  通过（Z）-烯醇与分子氧的金催化级联环化/氧化裂解反应裂解碳-碳三键

  摘要：

  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。

  DOI：

  10.1021/ja062610q
• 作为产物：
  描述：

  苯乙酮 、 苯基溴乙炔 、 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56%的产率得到(Z)-2,3,4,6-tetraphenylhex-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

• A general and efficient synthesis of substituted furans and dihydrofurans via gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols
  作者：Xiangwei Du、Feijie Song、Yuhua Lu、Haoyi Chen、Yuanhong Liu

  DOI：10.1016/j.tet.2008.11.109

  日期：2009.2

  A highly efficient Au-catalyzed cyclization of (Z)-enynols that proceeds under mild reaction conditions has been developed. This methodology provides rapid access to substituted furans and stereodefined (Z)-5-ylidene-2,5-dihydrofurans in a regioselective manner from suitably substituted (Z)-2-en-4-yn-1-ols.

  已经开发了在温和的反应条件下进行的高效Au催化（Z）-烯醇的环化反应。该方法学提供了从适当取代的（Z）-2-en-4-yn-1-ols上以区域选择性方式快速获得取代的呋喃和立体定义的（Z）-5-亚烷基-2,5-二氢呋喃的方法。
• Gold-Catalyzed Cyclization of (<i>Z</i>)-2-En-4-yn-1-ols:  Highly Efficient Synthesis of Fully Substituted Dihydrofurans and Furans
  作者：Yuanhong Liu、Feijie Song、Zhiquan Song、Meina Liu、Bin Yan

  DOI：10.1021/ol052160r

  日期：2005.11.1

  [reaction: see text] The gold-catalyzed cyclization of (Z)-enynols offers an efficient and straightforward route to stereodefined (Z)-5-ylidene-2,5-dihydrofurans and fully substituted furans under extremely mild reaction conditions. Importantly, the results indicated that both the oxyauration and the proto-demetalation steps are highly stereoselective.

  [反应：见正文]在极温和的反应条件下，金催化的（Z）-烯醇的环化反应提供了一条有效而直接的途径来合成立体定义的（Z）-5-亚烷基-2,5-二氢呋喃和完全取代的呋喃。重要的是，结果表明，氧化步骤和原脱金属步骤都是高度立体选择性的。
• 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.