(Z)-3-ethylpent-2-en-4-yn-1-ol | 250358-83-9

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: (Z)-3-ethylpent-2-en-4-yn-1-ol
• CAS: 250358-83-9
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: PWIOJZQAJHSIBM-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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)-3-ethylpent-2-en-4-yn-1-ol 在 palladium(II) iodide potassium iodide 作用下， 反应 18.0h， 以89%的产率得到2-methyl-3-ethylfuran
  参考文献：
  名称：

  A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (Z)-2-En-4-yn-1-ols

  摘要：

  A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 degrees C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.

  DOI：

  10.1021/jo990847h
• 作为产物：
  描述：

  3-乙基-1-戊烯-4-炔-3-醇 在 亚硫酸 作用下， 反应 2.0h， 以73%的产率得到(Z)-3-ethylpent-2-en-4-yn-1-ol
  参考文献：
  名称：

  A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (Z)-2-En-4-yn-1-ols

  摘要：

  A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 degrees C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.

  DOI：

  10.1021/jo990847h

文献信息

• Unprecedented endo-oxidative cyclometallation and [4 + 3] cycloaddition of diene-vinylcyclopropanes
  作者：Jun Yang、Pan Zhang、Zeyuan Shen、Yi Zhou、Zhi-Xiang Yu

  DOI：10.1016/j.chempr.2023.01.020

  日期：2023.2

  intramolecular [4 + 3] cycloaddition of Z-diene-vinylcyclopropanes (Z-diene-VCPs), which provide an efficient way to access challenging 5/7-fused bicyclic skeletons with a bridgehead ethyl substituent. In this [4 + 3] reaction, the Z-diene serves as a 4-carbon synthon, while the VCP acts as an unprecedented 3-carbon synthon (two carbon from the vinyl group and one carbon from the cyclopropyl group). Quantum

  传统的外氧化环金属化（exo -OCM）是过渡金属催化反应的关键步骤。在这里，我们首次提出内氧化环金属化 ( endo -OCM) 反应作为一种新的反应模式。endo -OCM的实现将为化学增加一个新概念，有助于未来endo- [m+n]、[m+n+o]环加成等反应的设计。我们在此报告内切-OCM 存在于新开发的 Rh(I) 催化的分子内 [4 + 3] 环加成Z-二烯-乙烯基环丙烷 ( Z-diene-VCPs)，它提供了一种有效的方法来获得具有桥头乙基取代基的具有挑战性的 5/7 稠合双环骨架。在这个 [4 + 3] 反应中，Z-二烯充当 4-碳合成子，而 VCP 充当前所未有的 3-碳合成子（两个碳来自乙烯基，一个碳来自环丙基）。已经进行了量子化学计算以分析影响外切-和内切-OCMs 竞争的因素，并理解为什么Z -diene-VCPs 的 [3 + 2] 和预期的 [4 + 3] 反应没有发生。
• An Efficient and General Synthesis of Furan-2-acetic Esters by Palladium-Catalyzed Oxidative Carbonylation of (<i>Z</i>)-2-En-4-yn-1-ols
  作者：Bartolo Gabriele、Giuseppe Salerno、Francesca De Pascali、Mirco Costa、Gian Paolo Chiusoli

  DOI：10.1021/jo990848+

  日期：1999.10.1

  A variety of (Z)-2-en-4-yn-1-ols have been carbonylated under oxidative conditions to give substituted furan-a-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 degrees C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (E)-2-[(alkoxycarbonyl)methylene]-2,5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.
• A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (<i>Z</i>)-2-En-4-yn-1-ols
  作者：Bartolo Gabriele、Giuseppe Salerno、Egidio Lauria

  DOI：10.1021/jo990847h

  日期：1999.10.1

  A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 degrees C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.