1,2,4-triphenethylbenzene | 1272671-86-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2,4-triphenethylbenzene
• 英文别名: 1,2,4-Tris(2-phenylethyl)benzene；1,2,4-tris(2-phenylethyl)benzene
• CAS: 1272671-86-9
• 化学式: C₃₀H₃₀
• 分子量: 390.568
• InChiKey: KZDKIGWTGOMWJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  4-苯基-1-丁炔 在 nickel(II) chloride hexahydrate 、 2-(1-methyl-2-benzimidazole)-6-(1-(2,6-dimethylphenyl)iminoethyl)pyridine 、 zinc(II) iodide 、 锌 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1,2,4-triphenethylbenzene 、 1,3,5-triphenethylbenzene
  参考文献：
  名称：

  Cyclotrimerization of terminal alkynes catalyzed by the system of NiCl2/Zn and (benzimidazolyl)-6-(1-(arylimino)ethyl)pyridines

  摘要：

  在室温下，通过一步法直接利用NiCl2·6H2O、Zn和2-(苯并咪唑基)-6-(1-(芳基亚胺)乙基)吡啶，实现了末端炔烃的高效区域选择性环三聚化反应。

  DOI：

  10.1039/c3dt51674a

文献信息

• Iron-catalyzed regioselective cyclotrimerization of alkynes to benzenes
  作者：Suhas Shahaji Gawali、Chidambaram Gunanathan

  DOI：10.1016/j.jorganchem.2018.12.007

  日期：2019.2

  catalyzed the regioselective [2+2+2] cyclotrimerization of terminal aryl and alkyl alkynes to provide the 1,2,4-trisubstituted benzene molecules. Interestingly, internal alkynes also exhibited similar cyclization and resulted in hexa-substituted benzene compounds. Increased steric bulk on pincer ligands diminished the selectivity for cycloaddition. Cyclotrimerization reactions proceeded at room temperature

  我们报告了简单的二（氨基甲基）吡啶连接的铁-钳配合物的合成和表征，它催化了末端芳基和烷基炔烃的区域选择性[2 + 2 + 2]环三聚反应，从而提供了1,2,4-三取代的苯分子。有趣的是，内部炔烃也表现出相似的环化作用，并产生六取代的苯化合物。钳位配体上增加的空间体积减少了对环加成反应的选择性。在通过格氏试剂活化催化剂后，在室温下进行环三聚反应。EPR研究表明，在催化剂中热诱导的自旋交叉效应。
• A Versatile, Functional Group‐Tolerant, and Bench‐Stable Iron Precatalyst for Building Arene and Triazine Rings by [2+2+2] Cycloadditions
  作者：William Parisot、Mansour Haddad、Phannarath Phansavath、Guillaume Lefèvre、Virginie Ratovelomanana‐Vidal

  DOI：10.1002/chem.202400096

  日期：2024.4.16

  A new [2+2+2] cycloaddition procedure relying on the use of an air-stable iron precatalyst is described, which allows the construction of aromatic and nitrogen-containing heteroaromatic rings in green solvents and mild conditions. Cycloadditions and cross-cycloadditions between 1,6- or 1,7-diynes and alkynes are reported, with a broad functional tolerance, leading to a variety of functionalizable scaffolds

  描述了一种依赖于使用空气稳定的铁预催化剂的新的[2+2+2]环加成过程，该过程允许在绿色溶剂和温和条件下构建芳香环和含氮杂芳环。据报道，1,6-或1,7-二炔与炔之间的环加成和交叉环加成具有广泛的功能耐受性，从而产生各种可功能化的支架。
• H-BPin/KO^<i>t</i>Bu Promoted Activation of Cobalt Salt to a Heterotopic Catalyst for Highly Selective Cyclotrimerization of Alkynes
  作者：Shuo Song、Chuhan Li、Tianfen Liu、Panke Zhang、Xiaoming Wang

  DOI：10.1021/acs.orglett.1c02493

  日期：2021.9.3
• Highly regioselective cyclotrimerization of terminal alkynes catalyzed by Fe(II) complexes bearing 2-(benzimidazolyl)-6-(1-(arylimino)ethyl)pyridines
  作者：Yongbing Liu、Xiaoyu Yan、Nianfa Yang、Chanjuan Xi

  DOI：10.1016/j.catcom.2010.11.013

  日期：2011.2

  FeCl2 ligated with 2-(benzimidazolyl)-6-(1-(arylimino)ethyl)pyridine in the presence of zinc powder and zinc iodide could effectively catalyze cyclotrimerization of intermolecular alkynes to afford benzene derivatives in high regioselectivity. The synthetic usefulness of this catalytic system consisting of Fe(II) complex C1, Zn and Znl(2) in acetonitrile was tested with various terminal alkynes. In the cases of using aryl substituted alkynes, the 1,2,4-trisubstituted benzenes 2 were found to be the major products. (C) 2010 Elsevier B.V. All rights reserved.
• Catalytic activity of a large Rhodium metallaborane towards the [2+2+2] cycloaddition of alkynes
  作者：Pei Ma、James T. Spencer

  DOI：10.1016/j.ica.2018.05.041

  日期：2018.10

  Rhodadecaborane [6-(-C5Me5)-nido-6-RhB9FH3] (1) was found to be able to catalyze the [2 + 2 + 2] cycloaddition of a series of terminal and internal alkynes to yield mixtures of 1,2,4- and 1,3,5 -substituted benzene. The reactivity of compound 1 with alkynes demonstrates that decaborane based metallaborane can be used as the catalyst for [2 + 2 + 2] cycloaddition of alkynes. All compounds are characterized by NMR spectroscopy and MS spectrometry methods.