5-phenylpent-2-en-4-ynenitrile | 49840-80-4

• 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: 5-phenylpent-2-en-4-ynenitrile
• 英文别名: (E)-5-phenylpent-2-en-4-ynenitrile
• CAS: 49840-80-4
• 化学式: C₁₁H₇N
• 分子量: 153.183
• InChiKey: ITLYTBNRXJVKLJ-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-phenylpent-2-en-4-ynenitrile 、 5,5-二甲基-1,3-环己二酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以84%的产率得到2-(2-benzyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-3-yl)acetonitrile
  参考文献：
  名称：

  A Metal-Free Tandem C–C/C–O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans

  摘要：

  A novel and efficient method for the synthesis of diversely functionalized furans is developed via DBU-mediated tandem Michael addition/5-exo-dig-cycloisomerization of enynes and keto-methylenes. This [3 + 2]-annulation is operationally simple under metal-free reaction conditions with 100% atom economy and broad substrate scope.

  DOI：

  10.1021/jo4023342
• 作为产物：
  描述：

  trans-3-(phenylethynyl)oxirane-2-carbonitrile 在 四甲基硫脲 作用下， 以 乙醇 为溶剂， 以91 %的产率得到5-phenylpent-2-en-4-ynenitrile
  参考文献：
  名称：

  硫脲介导的氰基环氧化物立体定向脱氧以获得高度非对映纯的烯基腈

  摘要：

  通过四甲基硫脲介导的乙醇中顺式和反式氰基环氧化物的立体定向脱氧，开发了一种实用且有效的合成> 99％非对映纯Z-和E-烯基腈的方案。以优异的收率获得了所需的产物。

  DOI：

  10.1021/acs.joc.3c02869

文献信息

• Stereoselective synthesis of vinyl nitriles through a Ramberg–Bäcklund approach
  作者：Octavio A. Valle-González、Ángel I. Salazar-Bello、J. Armando Luján-Montelongo

  DOI：10.1039/d3ob00214d

  日期：——

  applicability of vinyl nitriles in the preparation of pharmaceuticals, polymers, and other valuable materials benefits from robust preparative methodologies. In this work, we present a novel approach for the synthesis of vinyl nitriles based on the Ramberg–Bäcklund olefination reaction (RBR). While there are few examples for accessing functionalized olefins using the RBR, we believe that this methodology

  乙烯基腈在药物、聚合物和其他有价值材料制备中的适用性得益于可靠的制备方法。在这项工作中，我们提出了一种基于 Ramberg–Bäcklund 烯化反应 (RBR) 合成乙烯基腈的新方法。虽然很少有使用 RBR 获得功能化烯烃的例子，但我们相信这种方法体现了安装特权乙烯基腈构建单元的有用方法，例如美国 FDA 批准的抗病毒利匹韦林的丙烯腈片段。
• Synthesis of substituted acetylenes, aryl–alkyl ethers, 2-alkene-4-ynoates and nitriles using heterogeneous mesoporous Pd-MCM-48 as reusable catalyst
  作者：Subhash Banerjee、Hari Khatri、Vagulejan Balasanthiran、Ranjit T. Koodali、Grigoriy Sereda

  DOI：10.1016/j.tet.2011.05.132

  日期：2011.8

  Pd-MCM-48 has been employed as a heterogeneous catalyst for the synthesis of substituted acetylenes via Sonogashira reactions under copper and amine-free reaction conditions. In addition, the catalyst exhibited excellent regioselectivity for primary alcohols towards C-O coupling leading to formation of alkyl aryl ethers in high yields. A green procedure for the stereoselective synthesis of 2-alkene-4-ynoates and nitriles from the reactions of vic-(E)-diiodoalkenes with activated alkenes has also been demonstrated using Pd-MCM-48 catalyst. The catalyst was easily recovered from the reaction mixture by filtration and reused for at least six times with minimal loss of activity. (C) 2011 Elsevier Ltd. All rights reserved.
• A Metal-Free Tandem C–C/C–O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans
  作者：Chada Raji Reddy、Motatipally Damoder Reddy

  DOI：10.1021/jo4023342

  日期：2014.1.3

  A novel and efficient method for the synthesis of diversely functionalized furans is developed via DBU-mediated tandem Michael addition/5-exo-dig-cycloisomerization of enynes and keto-methylenes. This [3 + 2]-annulation is operationally simple under metal-free reaction conditions with 100% atom economy and broad substrate scope.
• Thiourea-Mediated Stereospecific Deoxygenation of Cyanoepoxides to Access Highly Diastereopure Alkenyl Nitriles
  作者：Yujie Zhang、Shukui Shi、Zhanhui Yang

  DOI：10.1021/acs.joc.3c02869

  日期：2024.2.16

  A practical and efficient protocol for synthesis of >99% diastereopure Z- and E-alkenyl nitriles is developed, through tetramethylthiourea-mediated stereospecific deoxygenation of respective cis- and trans-cyanoepoxides in ethanol. The desired products are obtained in excellent yields.

  通过四甲基硫脲介导的乙醇中顺式和反式氰基环氧化物的立体定向脱氧，开发了一种实用且有效的合成> 99％非对映纯Z-和E-烯基腈的方案。以优异的收率获得了所需的产物。