(Z)-1,4-diphenyl-2-(phenylamino)but-2-ene-1,4-dione | 29954-08-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (Z)-1,4-diphenyl-2-(phenylamino)but-2-ene-1,4-dione
• 英文别名: (Z)-1,4-diphenyl-2-phenylamino-2-butene-1,4-dione；2-anilino-1,4-diphenyl-but-2t-ene-1,4-dione；2-Anilino-1,4-diphenyl-but-2t-en-1,4-dion；trans-2-Anilino-1,4-diphenyl-but-2-en-1,4-dion；(Z)-2-anilino-1,4-diphenylbut-2-ene-1,4-dione
• CAS: 29954-08-3
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: LPGATJZHJUTVAG-SILNSSARSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  484.1±45.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1,4-diphenyl-2-(phenylamino)but-2-ene-1,4-dione 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.67h， 以97%的产率得到1,4-二苯基丁烷-1,2,4-三酮
  参考文献：
  名称：

  Synthesis, structure, and reactivity of 1,4-diaryl-2-(arylamino)but-2-ene-1,4-diones

  摘要：

  DOI：

  10.1021/jo00338a018
• 作为产物：
  描述：

  2,3-二苯胺基-1,4-二苯基丁烷-1,4-二酮 在 水 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.5h， 以77%的产率得到(Z)-1,4-diphenyl-2-(phenylamino)but-2-ene-1,4-dione
  参考文献：
  名称：

  (Z)-1,4-Diphenyl-2-phenylamino-2-butene-1,4-dione: Synthesis and Mechanizm of Formation

  摘要：

  Heating of 1-phenyl-2-(phenylamino)ethanone in a water-ethanol solution of potassium carbonate gave rise to (Z)-1,4-diphenyl-2-phenylamino-2-butene-1,4-dione; it formed most probably by reaction of the initial aminoketone with its oxidation product, 1-phenyl-2-(phenylimino)ethanone.

  DOI：

  10.1023/b:rujo.0000043716.91339.ea

文献信息

• Reduction of nitroarenes to anilines in basic alcoholic media
  作者：Maurizio Prato、Ugo Quintily、Gianfranco Scorrano

  DOI：10.1039/p29860001419

  日期：——

  azoxy and aniline derivatives. The reaction leading to anilines has been investigated in detail. Two different processes have been identified, both initiated by the condensation between the nitrosoarene intermediate (the first product of the reduction reaction) and the product of oxidation of the solvent. The imino derivative thus formed (ArNCH–COR) may either undergo hydrolysis (to aniline) or form

  取代的硝基苯在醇中被烷氧基离子还原为相应的氮氧基和苯胺衍生物。已经详细研究了导致苯胺的反应。已经鉴定出两种不同的方法，两者都是由亚硝基芳烃中间体（还原反应的第一产物）和溶剂的氧化产物之间的缩合引发的。由此形成的亚氨基衍生物（ArN CH-COR）可能会水解（生成苯胺），或者通过一系列氧化还原过程形成含有ArNH-CO部分的化合物。这些也会在较慢的反应中水解为苯胺。
• Use of [hydroxy(tosyloxy)iodo]benzene in a novel and facile synthesis of 1,4-diaryl-2-(arylamino)but-2-ene-1,4-diones
  作者：Om Prakash、Anita Batra、Vishwas Chaudhri、Richa Prakash

  DOI：10.1016/j.tetlet.2005.02.129

  日期：2005.4

  [hydroxy(tosyloxy)iodo]benzene followed by treatment of the resulting α-tosyloxyacetophenones 2 thus formed with anilines 3 in the presence of sodium carbonate in ethanol provides a novel one-pot synthesis of 1,4-diaryl-2-(arylamino)but-2-ene-1,4-diones 4.

  苯乙酮的反应1与[羟基（甲苯磺酰氧基）碘]苯，接着处理所得到的α-tosyloxyacetophenones的2因此与苯胺形成3在碳酸钠在乙醇中的存在提供1,4-二芳基的新颖的一锅法合成-2-（芳基氨基）丁-2-烯-1,4-二酮4。
• New reaction of mononitroarenes: Condensation with two acetophenone moleculesvia the nitro group
  作者：N. V. Moskalev、M. I. Tartynova、I. Yu. Bagryanskaya、Yu. V. Gatilov

  DOI：10.1007/bf01433996

  日期：1996.2

  Nitrobenzene,p-bromonitrobenzene,N,N-diethyl-p-nitroaniline, and 9-methyl-3nitrocarbazole undergo condensation with two moles of acetophenone in a DMSO-KOH system to form the corresponding (Z)-1,4-diphenyl-2-arylamino-2-butene-1,4-diones.

  硝基苯、对溴硝基苯、N,N-二乙基-对硝基苯胺和 9-甲基-3硝基咔唑在 DMSO-KOH 体系中与 2 摩尔苯乙酮缩合形成相应的 (Z)-1,4-二苯基-2 -芳氨基-2-丁烯-1,4-二酮。
• Regitz Diazo Transfer Reaction for the Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles and Subsequent Regiospecific Construction of 1,4-Disubstituted 1,2,3-Triazoles via C–C Bond Cleavage
  作者：Xue Cui、Xueying Zhang、Wei Wang、Xia Zhong、Yinfeng Tan、Yan Wang、Jianlan Zhang、Youbin Li、Xuesong Wang

  DOI：10.1021/acs.joc.0c02912

  日期：2021.3.5

  efficient methodology has been developed for the synthesis of 1,4,5-trisubstituted dicarbonyl 1,2,3-triazoles and 1,4-disubstituted sole-carbonyl 1,2,3-triazoles via a C–C bond cleavage process. The Regitz diazo transfer and C–C bond cleavage were the key steps of this transformation, which provided diverse carbonyl-substituted structural 1,2,3-triazoles. This reaction featured with excellent regioselectivity

  已经开发了一种直接有效的方法，可通过CC键断裂合成1,4,5-三取代的二羰基1,2,3-三唑和1,4-二取代的唯一羰基1,2,3-三唑过程。Regitz重氮转移和CC键断裂是该转化的关键步骤，它提供了各种羰基取代的结构1,2,3-三唑。该反应具有出色的区域选择性，宽泛的官能团耐受性和温和条件。
• Reactions of aromatic nitro compounds with acetophenone in the presence of alkali. Crystal structure of (E)-1,2-dibenzoyl-o-tolylaminoethylene
  作者：Lucedio Greci、Mirco Pieroni、Giorgio Tosi、Corrado Rizzoli、Paolo Sgarabotto、Franco Ugozzoli

  DOI：10.1007/bf01179915

  日期：1991.12

  Methyl and methoxy substituted nitroarenes were reacted with acethophenone in the presence of sodium ethoxide in ethanol giving arylamino-conjugated diketo derivatives. A case of ipso-substitution of a methoxy group is discussed. The title compound C23H19NO2 (M(r) = 341.4) crystallizes in the monoclinic system, space group P2(1)/n with a = 21.579(4), b = 8.526(2), c = 9.983(2) angstrom; beta = 92.3(1)-degrees; V = 1835.2(7) angstrom-3, Z = 4, D(c) = 1.24 g cm-3, mu(Cu-K-alpha) = 5.9 cm-1, lambda = 1.5418 angstrom, F(OOO) = 720. The molecule adopts the E configuration with the C = O carbonyl groups trans with respect to the ethylenic double bond.