1,3,5-trimethyl-2-(phenylbuta-1,3-diyn-1-yl)benzene | 1430234-84-6

• 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: 1,3,5-trimethyl-2-(phenylbuta-1,3-diyn-1-yl)benzene
• 英文别名: 1,3,5-Trimethyl-2-(4-phenylbuta-1,3-diynyl)benzene；1,3,5-trimethyl-2-(4-phenylbuta-1,3-diynyl)benzene
• CAS: 1430234-84-6
• 化学式: C₁₉H₁₆
• 分子量: 244.336
• InChiKey: UVOXDILUHTYZSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-mesityl-5-phenylpenta-1,4-diyn-3-one 在 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氯苯 作用下， 反应 24.5h， 以83%的产率得到1,3,5-trimethyl-2-(phenylbuta-1,3-diyn-1-yl)benzene
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y

文献信息

• Gold-Catalyzed Cadiot-Chodkiewicz-type Cross-Coupling of Terminal Alkynes with Alkynyl Hypervalent Iodine Reagents: Highly Selective Synthesis of Unsymmetrical 1,3-Diynes
  作者：Xiangdong Li、Xin Xie、Ning Sun、Yuanhong Liu

  DOI：10.1002/anie.201702833

  日期：2017.6.6

  A new and efficient method for the synthesis of unsymmetrical 1,3‐butadiynes by gold‐catalyzed C(sp)–C(sp) cross‐coupling of terminal alkynes with alkynyl hypervalent iodine(III) reagents has been developed. The reaction features high selectivity and efficiency, mild reaction conditions, wide substrate scope, and functional‐group compatibility, and is a highly attractive complement to existing methods

  开发了一种新的高效方法，该方法通过末端炔烃与炔基高价碘（III）试剂的金催化C（sp）–C（sp）交叉偶联来合成不对称1,3-丁二炔。该反应具有高选择性和高效率，温和的反应条件，广泛的底物范围和官能团相容性，是对现有方法的极具吸引力的补充。机理研究表明，形成菲咯啉基连接的金（I）络合物对于目标转化的效率和选择性至关重要。
• A recyclable Cu@C₂N nano-catalyst applied in the transformation of alkynes: pH switchable access to ketones and 1,3-diynes
  作者：Yuanjin Li、Tianyu Yang、Shuhui Wang、Zuqiang Bian、Zhiwei Liu

  DOI：10.1039/d3gc04314b

  日期：——

  The development of efficient noble metal-free heterogeneous catalysts with simple synthesis processes is of great value in synthetic chemistry. So far, the performance of heterogeneous catalysts under different acidic and alkaline conditions has rarely been considered. Herein, we demonstrate a multifunctional Cu@C2N catalyst for pH switchable hydration of alkynes and the Glaser–Hay reaction, with maximum

  开发合成工艺简单、高效、不含贵金属的多相催化剂在合成化学中具有重要价值。迄今为止，很少考虑多相催化剂在不同酸性和碱性条件下的性能。在此，我们展示了一种多功能Cu@C 2 N催化剂，用于炔烃的pH可切换水合和Glaser-Hay反应，最大产率分别达到92%和95%。高效的转化源于强大的金属-载体协同效应，因为C 2 N载体吸附反应底物，而Cu金属很好地活化反应底物，协同促进炔烃的转化。此外，Cu@C 2 N催化剂表现出良好的底物兼容性和可回收性，可以简单地回收并重复使用五次，而不会显着损失其催化活性。此外，Cu@C 2 N催化剂具有丰富的酸性和碱性位点，C 2 N可以很好地稳定Cu的价态和分散形式。这项工作证明了C 2 N基催化剂在催化领域的成功应用。有机合成领域，并为设计低成本、适应性广、环境友好的催化系统指出了方向。
• Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes
  作者：Alpay Dermenci、Rachel E. Whittaker、Guangbin Dong

  DOI：10.1021/ol400815y

  日期：2013.5.3

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.