(E)-1,2,4-triphenylbut-2-ene-1,4-dione | 34880-76-7

• 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: (E)-1,2,4-triphenylbut-2-ene-1,4-dione
• 英文别名: 1,2,4-triphenyl-(E-2)-buten-1,4-dione；1,2-dibenzoylstyrene；1,2,4-triphenyl-but-2t-ene-1,4-dione；1,2,4-Triphenyl-but-2t-en-1,4-dion；1,2,4-Triphenyl-buten-(2t)-dion-(1.4)；trans-1,2-Dibenzoyl-styrol；1,2,4-Triphenyl-2-butene-1,4-dione
• CAS: 34880-76-7
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: MEBZZSFHCRISAQ-CAPFRKAQSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• 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：

  (E)-1,2,4-triphenylbut-2-ene-1,4-dione 在 溶剂黄146 、 锌 作用下， 生成 2,3,5-三苯基呋喃
  参考文献：
  名称：

  The Reaction of 2,3-Dichloro-1,4-naphthoquinone with Salts of Alkyl Substituted and Unsubstituted Dithiocarbamic Acids

  摘要：

  DOI：

  10.1021/ja01151a138
• 作为产物：
  描述：

  4-oxo-2.4-diphenyl-trans-crotonic acid 在 五氯化磷 作用下， 生成 (E)-1,2,4-triphenylbut-2-ene-1,4-dione
  参考文献：
  名称：

  The Conformations of the cis and trans-Dibenzoylstyrenes

  摘要：

  DOI：

  10.1021/ja01119a065

文献信息

• Neue synthesen und reaktionen ungesättigter heterotitanacyclen
  作者：Stefan Dürr、Udo Höhlein、Rainer Schobert

  DOI：10.1016/0022-328x(93)80460-s

  日期：1993.10

  fragment by carbon (formation of vinylenic carbonates and the thia-derivatives of these) or by further heteroatoms like boron or phosphorus (formation of boroles and phosphoric acid derivatives), thus retaining the cyclofunctionality. Alternatively, some of the new chelate complexes can be readily CC-chain-lengthened via a deprotonating/alkylating sequence, leaving the metallacycle unaffected.

  二羰基钛茂金属与双官能羰基化合物（例如1,2-二酮和1,4-二酮-2-烯）与α-酮硫酮，α-酮亚胺，偶氮二碳酸酯和-酰胺发生化学选择性反应，生成相应的，大多为新的杂七碳六环能够进行许多有用的后续反应。这些包含三到四个杂原子的螯合物，可以使整个钛茂片段被碳（碳酸亚乙烯酯碳酸盐和它们的硫杂衍生物的形成）或其他杂原子如硼或磷（硼烷和磷酸衍生物的形成）取代，从而保留了环功能。另外，一些新的螯合配合物可以很容易地通过去质子化/烷基化的顺序被CchainC链加长，而使金属环不受影响。
• Ceric Ammonium Nitrate Promoted Oxidative Coupling of Terminal Alkynes and 1,3-Keto Esters: A Synthesis of Unsymmetrical 1,1,2-Triacylalkenes
  作者：Charnsak Thongsornkleeb、Sureeporn Ruengsangtongkul、Takahito Kuribara、Nattawadee Chaisan、Jumreang Tummatorn、Somsak Ruchirawat

  DOI：10.1055/a-1774-6966

  日期：2022.9

  Unsymmetrical 1,1,2-triacylalkenes were conveniently prepared by the oxidative coupling of 1,3-keto esters with terminal alkynes by employing 4.0 equivalents of inexpensive ceric ammonium nitrate (CAN) as the oxidant in acetonitrile as the solvent at 0 °C. The method is milder than previously reported methods and can be conducted under air, thereby demonstrating its practicality and versatility for

  不对称的 1,1,2-三酰基烯烃是通过 1,3-酮酯与末端炔烃的氧化偶联，在 0 °C 下使用 4.0 当量廉价的硝酸铈铵 (CAN) 作为氧化剂，以乙腈为溶剂，方便地制备的。该方法比以前报道的方法更温和，并且可以在空气中进行，从而证明了它在制备这些有用的构件方面的实用性和多功能性。该反应被认为是通过由 CAN 引发的 1,3-酮酯底物的单电子转移过程发生的，以产生 α-自由基物质，该物质迅速添加到反应中的末端炔烃伴侣。随后通过空气和 CAN 对所得乙烯基自由基进行氧化，然后导致形成作为 E 和 Z 异构体混合物的三酰基烯烃产物。反应被证明是一般的，
• Successively Recycle Waste as Catalyst: A One-Pot Wittig/1,4-Reduction/Paal–Knorr Sequence for Modular Synthesis of Substituted Furans
  作者：Long Chen、Yi Du、Xing-Ping Zeng、Tao-Da Shi、Feng Zhou、Jian Zhou

  DOI：10.1021/acs.orglett.5b00442

  日期：2015.3.20

  A one-pot tandem Wittig/conjugate reduction/PaalKnorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.
• Rajakumar, Perumal; Kannan, Arunachalam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 12, p. 1275 - 1277
  作者：Rajakumar, Perumal、Kannan, Arunachalam

  DOI：——

  日期：——
• 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.