1,3,5-triphenylpent-2-en-4-yn-1-ol | 896106-09-5

• 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: 1,3,5-triphenylpent-2-en-4-yn-1-ol
• 英文别名: (Z)-1,3,5-Triphenyl-pent-2-en-4-yn-1-ol；(Z)-1,3,5-triphenylpent-2-en-4-yn-1-ol
• CAS: 896106-09-5
• 化学式: C₂₃H₁₈O
• 分子量: 310.395
• InChiKey: GONQYWWKORVMAG-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：
  0.04
• 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：

  1,3,5-triphenylpent-2-en-4-yn-1-ol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 以50%的产率得到(3,5-diphenyl-2-furyl)(phenyl)methanone
  参考文献：
  名称：

  通过IBX介导的顺式2-En-4-yn-1-醇（IBX = 2-碘氧基苯甲酸）级联氧化/环化反应构建多取代的2-酰基呋喃的新合成方法。

  摘要：

  DOI：

  10.1002/chem.200801561
• 作为产物：
  描述：

  苯甲醛 、 苯乙炔 在 potassium tert-butylate 、 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.05h， 生成 1,3,5-triphenylpent-2-en-4-yn-1-ol
  参考文献：
  名称：

  Tandem reactions of cis-2-acyl-1-alkynyl-1-aryl cyclopropanes tuned by gold(i) and silver(i) catalysts: efficient synthesis of pyran-fused indene cores and 2,4,6-trisubstituted phenols

  摘要：

  文中描述了顺式-2-酰基-1-炔基-1-芳基环丙烷 1 在金（I）和银（I）催化剂作用下的串联反应，这些反应分别以良好的收率选择性地获得了关键的吡喃融合茚核 2 和 2,4,6-三取代酚 3。

  DOI：

  10.1039/b909181e

文献信息

• Gold-Catalyzed Intermolecular Reactions of (<i>Z</i>)-Enynols with Indoles for the Construction of Dihydrocyclohepta[<i>b</i>]indole Skeletons through a Cascade Friedel-Crafts/Hydroarylation Sequence
  作者：Yuhua Lu、Xiangwei Du、Xueshun Jia、Yuanhong Liu

  DOI：10.1002/adsc.200900068

  日期：2009.7

  An efficient domino approach for the synthesis of indole‐fused carbocycles and their analogues from the reactions of suitably substituted (Z)‐enynols with indoles or pyrroles under mild reaction conditions was developed. This methodology is realized by a tandem reaction using Au/Ag catalysts, which could catalyze both of the Friedel–Crafts and the hydroarylation reaction in the same vessel.

  在温和的反应条件下，通过适当取代的（Z）烯醇与吲哚或吡咯的反应，开发了一种高效的多米诺骨牌合成吲哚稠合碳环及其类似物的方法。这种方法是通过使用Au / Ag催化剂的串联反应实现的，它可以在同一容器中催化Friedel-Crafts和加氢芳基化反应。
• An Efficient Domino Approach for the Synthesis of Multisubstituted Pyrroles via Gold/Silver-Catalyzed Amination/Cycloisomerization of (Z)-2-En-4-yn-1-ols
  作者：Yuhua Lu、Xiaoping Fu、Haoyi Chen、Xiangwei Du、Xueshun Jia、Yuanhong Liu

  DOI：10.1002/adsc.200800490

  日期：2009.1

  An efficient and one-pot synthesis of multisubstituted pyrroles with high diversity and in a regioselective manner from the reactions of suitably substituted (Z)-enynols with amines or sulfonamides under mild reaction conditions has been developed. This synthesis was realized via a cascade process in the presence of gold/silver (Au/Ag) or boron trifluoride⋅etherate/gold/silver (BF3⋅Et2O/Au/Ag) catalysts

  已经开发了由适当取代的（Z）-烯醇与胺或磺酰胺在温和的反应条件下的反应以区域选择性的方式高效且一锅合成高多样性的多取代吡咯的方法。该合成实现了通过在金/银（金/银）的存在下，级联过程或硼trifluoride⋅etherate/金/银（BF 3 ⋅Et 2 O /金/银）催化剂，它可以催化胺化和环异构反应在同一艘船上。
• 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 Cascade Friedel−Crafts/Furan−Alkyne Cycloisomerizations for the Highly Efficient Synthesis of Arylated (<i>Z</i>)-Enones or -Enals
  作者：Yifeng Chen、Yuhua Lu、Guijie Li、Yuanhong Liu

  DOI：10.1021/ol901408u

  日期：2009.9.3

  An efficient domino approach for the synthesis of arylated (Z)-enones or -enals through gold(I)-catalyzed reactions of enynols with furans was developed. PPh3AuNTf2 was found to be an excellent catalyst to catalyze both of the Friedel−Crafts and furan/alkyne cyclization reactions in the same vessel. This method offers several advantages such as high stereoselectivities, mild reaction conditions, and

  通过金（I）催化的烯醇与呋喃的反应，开发了一种有效的多米诺骨牌合成芳基化的（Z）-烯酮或-烯醛的方法。发现PPh 3 AuNTf 2是在同一容器中催化Friedel-Crafts和呋喃/炔烃环化反应的出色催化剂。该方法具有许多优点，例如高的立体选择性，温和的反应条件和易于获得的起始原料。
• KO<i>^t</i>Bu-Promoted Three-Component Coupling of Aldehydes and Alkynes:  Highly Efficient Synthesis of 1-En-4-yn-3-ols and 2-En-4-yn-1-ols
  作者：Shao-Hua Wang、Yong-Qiang Tu、Peng Chen、Xiang-Dong Hu、Fu-Min Zhang、Ai-Xia Wang

  DOI：10.1021/jo0604078

  日期：2006.5.1

  A (KOBu)-Bu-t-promoted three-component coupling reaction of aldehydes and alkynes without a transition-metal catalyst was developed in which the sequential addition/isomerization/addition processes take place in one pot. This reaction could be developed into a straightforward and effective method for rapid access to stereodefined (E)-1-en-4-yn-3-ol and (Z)2-en-4-yn-1-ol compounds.