1,4-bis-(4-bromo-phenyl)-but-2-yne-1,4-dione | 132665-87-3

• 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: 1,4-bis-(4-bromo-phenyl)-but-2-yne-1,4-dione
• 英文别名: 1,4-Bis-(4-brom-phenyl)-but-2-in-1,4-dion；Di-(4-brombenzoyl)acetylen；1,4-Bis(4-bromophenyl)but-2-yne-1,4-dione
• CAS: 132665-87-3
• 化学式: C₁₆H₈Br₂O₂
• 分子量: 392.046
• InChiKey: JGCHTEWWPSETQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,4-bis-(4-bromo-phenyl)-but-2-yne-1,4-dione 在 polypyrrole stabilized palladium nanoparticles 、 formate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以94%的产率得到1,4-二(4-溴苯基)丁烷-1,4-二酮
  参考文献：
  名称：

  聚合物稳定的钯纳米粒子，用于α，β-不饱和羰基的化学选择性转移加氢：一步步自下而上的方法

  摘要：

  聚吡咯稳定的钯纳米粒子对α，β-不饱和羰基化合物的化学选择性转移氢化显示出良好的催化效率。该催化剂是非常特殊的，并且仅选择性地氢化烯烃或乙炔，而不会影响羰基部分，对于广泛的底物具有优异的产物收率。

  DOI：

  10.1002/cctc.201300985
• 作为产物：
  描述：

  2,3-dibromo-1,4-bis-(4-bromo-phenyl)-butane-1,4-dione 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 1,4-bis-(4-bromo-phenyl)-but-2-yne-1,4-dione
  参考文献：
  名称：

  路易斯酸催化的一锅三组分途径可合成手性3,3'-联吡咯。

  摘要：

  3,3'-联吡咯3可以使用双迈克尔加成反应合成，该反应涉及使用乙酸铵作为氮源的二芳酰基乙炔1和适当的1,3-二羰基2。通过X射线晶体结构和DFT计算可以预测联吡咯的轴向手性，并通过分离手性柱上的外消旋物和随后的对映体CD光谱来确认。对映异构体的绝对构型是使用ZINDO方法通过理论CD光谱计算获得的。

  DOI：

  10.1021/ol800115p

文献信息

• InCl3 Catalysed One-Pot Synthesis of Substituted Pyrroles and 2-Pyrones
  作者：Sanjit K. Mahato、Jayaraman Vinayagam、Sumit Dey、Ajay K. Timiri、Sourav Chatterjee、Parasuraman Jaisankar

  DOI：10.1071/ch12359

  日期：——

  An efficient InCl3 catalysed one-pot strategy has been developed for the synthesis of tetra-substituted pyrroles and tri-substituted 2-pyrones in very good yields. Tetra-substituted pyrroles were prepared from 1,4-enediones and β-dicarbonyls employing NH4OAc as a nitrogen source, through a combination of Michael addition and Paal–Knorr methods. Tri-substituted 2-pyrones were synthesised from 1,4-ynediones and appropriate β-dicarbonyls using a sequential Michael addition and 6-exo-trig cyclisation.

  我们开发出了一种在 InCl3 催化下高效合成四取代吡咯和三取代 2-吡咯的单锅策略，收率非常高。以 NH4OAc 为氮源，通过迈克尔加成法和 Paal-Knorr 法相结合的方法，从 1,4-负离子和 β-二羰基制备了四取代吡咯。采用迈克尔加成法和 6-外-三环化法，从 1,4-炔二酮和适当的 β-二羰基合成了三取代 2-吡咯。
• Woollins Reagent: A Chemoselective Reducing Agent for 1,4-Enediones and 1,4-Ynediones to Saturated 1,4-Diones
  作者：Parasuraman Jaisankar、Madhumita Mandal、Sourav Chatterjee

  DOI：10.1055/s-0032-1317343

  日期：——

  Woollins reagent was found to act as a highly chemoselective reagent for the reduction of a wide range of 1,4-enediones and 1,4-ynediones in methanol to afford the corresponding saturated 1,4-diketones in good yields under mild reaction conditions.
• Facile Microwave-Mediated Transformations of 2-Butene-1,4-diones and 2-Butyne-1,4-diones to Furan Derivatives
  作者：H. Surya Prakash Rao、S. Jothilingam

  DOI：10.1021/jo0341766

  日期：2003.6.1

  Several di- and triarylfuran derivatives were prepared in high yields from but-2-ene-1,4-diones/but-2-yne-1,4-diones using formic acid in the presence of a catalytic amount of palladium on carbon and in poly(ethylene glycol)200 medium in a one-pot operation under microwave irradiation (1-5 min).
• Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones
  作者：H.Surya Prakash Rao、S Jothilingam、Hans W Scheeren

  DOI：10.1016/j.tet.2003.11.087

  日期：2004.2

  Several pyrrole derivates with multiple aryl substituents were prepared conveniently in a one pot-reaction from but-2-ene-1,4-diones and but-2-yne-1,4-diones via hydrogenation of the carbon-carbon double bond/triple bond followed by amination-cyclization. The reaction could be performed with ammonium formate or alkyl/arylammonium formates under Pd/C in polyethylene glycol-200 (PEG-200) under microwave irradiation. Using this procedure, different aryl-substituted pyrroles were prepared. Furthermore, studies on microwave vs thermal conditions indicate faster heating under microwave conditions was responsible for rate enhancement. (C) 2003 Elsevier Ltd. All rights reserved.
• THE REACTIONS OF THE DIBROMIDES AND BROMO DERIVATIVES OF DIBENZOYLETHYLENE WITH AMINES
  作者：ROBERT E. LUTZ、WILLIAM R. SMITHEY

  DOI：10.1021/jo01141a008

  日期：1951.1