bis(2,5-dimethylbenzoyl)acetylene | 885357-75-5

• 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: bis(2,5-dimethylbenzoyl)acetylene
• 英文别名: 2-Butyne-1,4-dione, 1,4-bis(2,5-dimethylphenyl)-；1,4-bis(2,5-dimethylphenyl)but-2-yne-1,4-dione
• CAS: 885357-75-5
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: JGIJLYDJIXHAQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(2,5-dimethylbenzoyl)acetylene 以 苯 为溶剂， 反应 1.41h， 生成 4,5-bis(2,5-dimethylbenzoyl)-1-phenyl-1H-pyrrole-2,3-dione
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXXIII. Synthesis and thermolysis of 1-aryl-4,5-diaroyl-1H-pyrrole-2,3-diones

  摘要：

  The reaction of (Z)-2-amino-1,4-diarylbut-2-en-1,4-diones with oxalyl chloride led to the formation of 1-aryl-4,5-diaroyl-1H-pyrrole-2,3-diones that at the thermal decarbonylation gave aroyl(N-arylimidoyl)ketenes which underwent stabilization by molecular cyclization into 2,3-diaroylquinolin-4(1H)-ones.

  DOI：

  10.1134/s1070428012020145

文献信息

• A Novel, One-Pot, Efficient Synthesis of 2-Aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones
  作者：Mehdi Adib、Mohammad Sayahi、Hakimeh Ziyadi、Long-Guan Zhu、Hamid Bijanzadeh

  DOI：10.1055/s-0028-1083157

  日期：——

  A novel and efficient synthesis of 2-aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones is described. The reactive 1:1 zwitterionic intermediate, formed by the addition of triphenylphosphine to diaroylacetylenes, was trapped by a Knoevenagel condensation product prepared in situ by reaction of N,N-dimethylbarbituric acid and aromatic aldehydes, to afford the title compounds in excellent yields under mild reaction conditions.

  本文描述了一种新颖且高效的合成2-aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones的方法。通过三苯基膦与二芳酰炔的加成反应生成的反应性1:1两性离子中间体，被在原位通过N,N-二甲基巴比妥酸与芳香醛反应制备的Knoevenagel缩合产物捕获，从而以优异产率在温和的反应条件下获得了目标化合物。
• Efficient synthesis of imidazo[1,2-a]pyridin-3(2H)-ones
  作者：Mehdi Adib、Mohammad Mahdavi、Alireza Abbasi、Amin Haghighat Jahromi、Hamid Reza Bijanzadeh

  DOI：10.1016/j.tetlet.2007.03.021

  日期：2007.4

  2-Aminopyridines react with diaroylacetylenes to produce imidazo[1,2-a]pyridin-3(2H)-ones in good to excellent yields.

  2-氨基吡啶与二芳酰基乙炔反应生成咪唑并[1,2 - a ]吡啶-3-3 （2 H）-酮，产率高至优异。
• Facile One-Pot Three-Component Synthesis of Functionalized Pyridylfuran-2-amines
  作者：Mehdi Adib、Mohammad Hosein Sayahi、Somayeh Aali Koloogani、Peiman Mirzaei

  DOI：10.1002/hlca.200690034

  日期：2006.2

  The reactive 1 : 1 zwitterionic intermediates generated in situ from the reaction between a series of isocyanides and diaroylacetylenes were trapped by pyridine carbaldehydes to yield highly functionalized 5-pyridylfuran-2-amines in good yields (82–93%).

  由一系列异氰化物和二芳酰基乙炔之间的反应原位生成的反应性1：1两性离子中间体被吡啶甲醛捕获，以高产率（82-93％）得到高度官能化的5-吡啶基呋喃-2-胺。
• A novel reaction between benzothiazoles and diaroylacetylenes in the presence of Meldrum’s acid: ring expansion of benzothiazoles to functionalized 1,4-benzothiazines
  作者：Mehdi Adib、Esmaeil Sheibani、Long-Guan Zhu、Hamid Reza Bijanzadeh

  DOI：10.1016/j.tetlet.2009.04.110

  日期：2009.8

  A novel and efficient ring expansion of benzothiazoles to functionalized 1,4-benzothiazines is described. The reactive 1:1 zwitterionic intermediates formed by addition of benzothiazoles to diaroylacetylenes were trapped with Meldrum’s acid under mild reaction conditions to produce 2-[2-hydroxy-2-aryl-2H-1,4-benzothiazin-3(4H)-yliden]-1-aryl-1-ethanones in excellent yields.

  描述了新颖且有效的苯并噻唑环扩环为官能化的1，4-苯并噻嗪。在温和的反应条件下，将由苯并噻唑加成到二芳酰基乙炔中形成的反应性1：1两性离子中间体用Meldrum酸捕获，生成2- [2-羟基-2-芳基-2 H -1,4-苯并噻嗪-3（4 H） -yliden] -1-芳基-1-乙炔具有极好的收率。
• A novel, one-pot and three-component synthesis of α-quinoxalinyl triphenylphosphoranes
  作者：Mehdi Adib、Esmaeil Sheibani、Alireza Abbasi、Hamid Reza Bijanzadeh

  DOI：10.1016/j.tetlet.2006.12.079

  日期：2007.2

  The reactive 1: 1 zwitterionic intermediate formed by the addition of triphenylphosphine to diaroylacetylenes was trapped with 1,2-benzenediamines to produce triphenylphosphorane intermediates. Intramolecular cyclization and subsequent oxidation of the intermediate afforded functionalized alpha-quinoxalinyl triphenylphosphoranes in good to excellent yields. (c) 2006 Elsevier Ltd. All rights reserved.