1,2,4-triethoxycarbonyl-3,5,6-triphenylbenzene | 91620-97-2

• 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: 1,2,4-triethoxycarbonyl-3,5,6-triphenylbenzene
• 英文别名: Triethyl 3,5,6-triphenylbenzene-1,2,4-tricarboxylate
• CAS: 91620-97-2
• 化学式: C₃₃H₃₀O₆
• 分子量: 522.598
• InChiKey: XBCDPUBVJOLWLF-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C
• 沸点：
  688.3±55.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,4-triethoxycarbonyl-3,5,6-triphenylbenzene 在 硫酸 作用下， 反应 0.08h， 以40%的产率得到9,14,15-Trioxo-14,15-dihydro-9H-diindeno<1,2-a;2',1'-c>fluoren
  参考文献：
  名称：

  Facile Multistep Synthesis of Isotruxene and Isotruxenone

  摘要：

  Three multistep approaches toward facile syntheses of isotruxene (1) and isotruxenone (3) are reported. The ortho-para conjugated backbone in the precursor 4 was constructed by either Co-catalyzed [2 + 2 + 2] cyclotrimerization or the [4 + 2] Diels-Alder reactions. The regioselectivity of the triple intramolecular Friedel-Crafts acylation of 4 plays the key role in determining the overall yield. Compared to the previous one-step method, the current approaches are more efficient in terms of product yield (27-36% vs 4-18%) and purification (i.e., free of column chromatography).

  DOI：

  10.1021/jo900299q
• 作为产物：
  描述：

  苯丙炔酸乙酯 在 rhodium(III) chloride 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到1,2,4-triethoxycarbonyl-3,5,6-triphenylbenzene
  参考文献：
  名称：

  RhCl₃/Amine-catalyzed Cyclotrimerization of Alkynes

  摘要：

  RhCl3/胺被发现是炔烃环三聚反应的有效催化剂。内炔的[2+2+2]环三聚反应顺利进行， regioselectively生成六取代苯，产率为中等至高。

  DOI：

  10.1246/cl.2007.998

文献信息

• Cyclotrimerization of alkynes catalyzed by a self-supported cyclic tri-nuclear nickel(0) complex with α-diimine ligands
  作者：Lingyi Shen、Yanxia Zhao、Qiong Luo、Qian-Shu Li、Bin Liu、Carl Redshaw、Biao Wu、Xiao-Juan Yang

  DOI：10.1039/c9dt00819e

  日期：——

  α-diimine nickel(0) complex [Ni(μ-LMe-2,4)}3] (2) was synthesized from a “pre-organized”, trimerized trigonal LNiBr2-type precursor [Ni3(μ2-Br)3(μ3-Br)2(LMe-2,4)3]·Br (1; LMe-2,4 = [(2,4-Me2C6H3)NC(Me)]2). In complex 2, the α-diimine ligands not only exhibit the normal N,N′-chelating mode, but they also act as bridges between the Ni atoms through an unusual π-coordination of a CN bond to Ni. Complex 2 is

  环状三核α-二亚胺镍（0）络合物[Ni（μ- LMe -2,4）} 3 ]（2）是由“预组织”的三聚LNiBr 2型三方前体[倪3（μ 2 -Br）3（μ 3 -Br）2（L ME-2,4）3 ]·能Br（1 ; l ME-2,4 = [（2,4--ME 2 ç 6 ħ 3）NC（Me）] 2）。在配合物2中，α-二亚胺配体不仅表现出正常的N，N'-螯合模式，但它们也通过C N键与Ni的不寻常π配位而充当Ni原子之间的桥梁。配合物2能够催化炔烃的环三聚反应以形成高产率和对1,3,5-异构体的区域选择性的取代苯，这随所用炔烃的性质而变化。该络合物代表一种方便的自支撑镍（0）催化剂，不需要其他配体和还原剂。
• RhCl₃/Amine-catalyzed Cyclotrimerization of Alkynes
  作者：Kenta Yoshida、Ichiro Morimoto、Koichi Mitsudo、Hideo Tanaka

  DOI：10.1246/cl.2007.998

  日期：2007.8.5

  RhCl3/amine was found to be an efficient catalyst for the cyclotrimerization of alkynes. The [2+2+2] cyclotrimerization of internal alkynes proceeded smoothly to afford hexa-substituted benzenes regioselectively in moderate to high yields.

  RhCl3/胺被发现是炔烃环三聚反应的有效催化剂。内炔的[2+2+2]环三聚反应顺利进行， regioselectively生成六取代苯，产率为中等至高。
• Ni‐Catalyzed Regioselective Cyclotrimerization of Internal Esteryl Alkynes towards Polysubstituted Benzene Rings
  作者：Chao Hou、Yan Ma、Yongqi Zhang、Huiling Xu、Yuanqi Wu、Jinbo Zhao、Yuchao Wang、Yu Liu

  DOI：10.1002/hlca.202200005

  日期：2022.5

  Transition-metal-catalyzed [2+2+2] cycloaddition of alkynes is a core synthetic approach to benzene rings. Herein we describe an efficient system based on inexpensive nickel catalyst and phosphine ligand that facilitate cyclotrimerization of various internal esteryl alkynes. The regioselectivity of the protocol was precisely controlled, and a series of polysubstituted benzene rings mainly composed

  过渡金属催化的炔烃的 [2+2+2] 环加成是苯环的核心合成方法。在此，我们描述了一种基于廉价镍催化剂和膦配体的高效系统，该系统有助于各种内部酯基炔烃的环三聚化。该方案的区域选择性得到精确控制，提供了一系列主要由1,2,4-异构体组成的多取代苯环。
• Diercks, Rainer; Dieck, Heindirk tom, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 2, p. 180 - 184
  作者：Diercks, Rainer、Dieck, Heindirk tom

  DOI：——

  日期：——
• RhCl3/amine-catalyzed [2+2+2] cyclization of alkynes
  作者：Kenta Yoshida、Ichiro Morimoto、Koichi Mitsudo、Hideo Tanaka

  DOI：10.1016/j.tet.2008.03.079

  日期：2008.6

  The RhCl3-3H(2)O/i-Pr2NEt-catalyzed [2+2+2] cyclotrimerization of alkynes has been achieved. The reaction can be widely used for various alkynes and provides tri- OF hexa-substituted benzenes regioselectively in high yields. The [2+2+2] cycloaddition of diynes and alkynes is also developed, and it affords benzene derivatives in moderate to high yields. (C) 2008 Elsevier Ltd. All rights reserved.