(E)-1,4-bis(4-chloro-3-methylphenyl)-2-butene-1,4-dione | 96576-98-6

• 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: (E)-1,4-bis(4-chloro-3-methylphenyl)-2-butene-1,4-dione
• 英文别名: 1,4-bis-(4-chloro-3-methyl-phenyl)-but-2-ene-1,4-dione；α.β-Bis-(4-chlor-3-methyl-benzoyl)-aethylen；1,4-Bis-(4-chlor-3-methyl-phenyl)-but-2-en-1,4-dion；1,2-Bis-(p-chlor-m-methylbenzoyl)-ethylen；(E)-1,4-bis(4-chloro-3-methylphenyl)but-2-ene-1,4-dione
• CAS: 96576-98-6
• 化学式: C₁₈H₁₄Cl₂O₂
• 分子量: 333.214
• InChiKey: LGJAJSXLXSODBP-BQYQJAHWSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  491.0±45.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  (E)-1,4-bis(4-chloro-3-methylphenyl)-2-butene-1,4-dione 在 palladium on activated charcoal 甲酸 作用下， 以 various solvent(s) 为溶剂， 反应 0.02h， 以96%的产率得到2,5-bis(4-chloro-3-methylphenyl)furan
  参考文献：
  名称：

  Facile Microwave-Mediated Transformations of 2-Butene-1,4-diones and 2-Butyne-1,4-diones to Furan Derivatives

  摘要：

  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).

  DOI：

  10.1021/jo0341766
• 作为产物：
  描述：

  反丁烯二酰氯 、 2-氯甲苯 在 二硫化碳 、 三氯化铝 作用下， 生成 (E)-1,4-bis(4-chloro-3-methylphenyl)-2-butene-1,4-dione
  参考文献：
  名称：

  Conant; Lutz, Journal of the American Chemical Society, 1925, vol. 47, p. 890

  摘要：

  DOI：

文献信息

• One-pot synthesis of pyrrole derivatives from (E)-1,4-diaryl-2-butene-1,4-diones
  作者：H Surya Prakash Rao、S Jothilingam

  DOI：10.1016/s0040-4039(01)01334-x

  日期：2001.9

  2,5-Di- and 1,2,5-trisubstituted pyrrole derivatives can be prepared conveniently from (E)-1,4-diaryl-2-butene-1,4-diones in a one-pot operation through domino-pathways via palladium-assisted transfer hydrogenation followed by a Paal–Knorr reaction using ammonium formate and its analogs.

  可通过一锅操作通过多米诺途径方便地从（E）-1,4-二芳基-2-丁烯-1,4-二酮制备2,5-二-和1,2,5-三取代的吡咯衍生物通过钯辅助的转移氢化反应，然后使用甲酸铵及其类似物进行Paal-Knorr反应。
• Newly Synthesized 3-Indolyl Furanoid Inhibits Matrix Metalloproteinase-9 Activity and Prevents Nonsteroidal Anti-inflammatory Drug-Induced Gastric Ulceration
  作者：Deep Sankar Rudra、Sourav Chatterjee、Uttam Pal、Madhumita Mandal、Susri Ray Chaudhuri、Mrinmay Bhunia、Nakul Chandra Maiti、Shila Elizabeth Besra、Parasuraman Jaisankar、Snehasikta Swarnakar

  DOI：10.1021/acs.jmedchem.3c00511

  日期：2023.7.13

  Indomethacin, a known nonsteroidal anti-inflammatory drug (NSAID) induces gastric inflammation, causing degradation of the extracellular matrix by specific matrix metalloproteinases (MMPs). We investigated the antiulcer efficacy of 3-indolyl furanoids (3g and 3c, i.e., methoxy substitution at 4- and 5-positions of the indole ring, respectively), derived from indomethacin. Interestingly, 3g protected

  吲哚美辛是一种已知的非甾体类抗炎药 (NSAID)，它会诱发胃部炎症，导致特定基质金属蛋白酶 (MMP) 降解细胞外基质。我们研究了源自吲哚美辛的 3-吲哚基呋喃类化合物（3g和3c，即分别在吲哚环的 4 位和 5 位上进行甲氧基取代）的抗溃疡功效。有趣的是，3g通过抑制 MMP-9 来预防体内吲哚美辛诱发的胃病。我们的工作制定了化学修饰策略，以开发更安全的非甾体抗炎药。此外，体外和计算机研究证实，3g通过与 MMP-9 的催化裂隙结合，抑制 MMP-9 活性，IC 50值为 50 μM，从而预防溃疡。药代动力学以大鼠血浆中的平均浓度-时间曲线表示，提取效率大于 70%，处理6.0 小时 ( t max ) 后的C max为 104.48 μg/mL ，半衰期和面积均在曲线分别为 7.0 h 和 1273.8 h μg/mL，表明3g的抗溃疡效力较高。
• <b>The Base-catalyzed Addition of Methanol to Dibenzoylethylenes</b>
  作者：Thomas I. Crowell、Grover C. Helsley、Robert E. Lutz、William L. Scott

  DOI：10.1021/ja00887a016

  日期：1963.2
• 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.
• Domino Michael−Aldol Reactions on 1,4-Diarylbut-2-ene-1,4-diones with Methyl Acetoacetate Furnish Methyl 2-Aroyl-4- hydroxy-6-oxo-4-arylcyclohexane-1-carbox- ylate Derivatives
  作者：H. Surya Prakash Rao、S. P. Senthilkumar

  DOI：10.1021/jo0353839

  日期：2004.4.1

  Domino Michael-Aldol reactions on 1,4-diaryl-2-butene-1,4-diones with methyl acetoacetate in the presence of activated Ba(OH)(2) furnished methyl (1R*,2S*,4S*)-2-aroyl-4-hydroxy-6-oxo-4-arylcyclohexane-1-carboxylate derivatives in a stereo- and regiospecific manner. While treatment of these cyclohexanecarboxylate products with TsOH resulted in the dehydrated and decarbomethoxylated cyclohexenone derivatives, the reaction with NaOMe furnished 3,5-disubstituted phenols via dehydration, decarbomethoxylation, and dehydrogenation. NaCl/DMSO under microwave irradiation transformed the cyclohexanecarboxylate products to the 7-hydroxyisobenzofuranone derivatives.