3,4-diphenylcyclobut-3-ene-1,2-dione | 24234-76-2

• 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: 3,4-diphenylcyclobut-3-ene-1,2-dione
• 英文别名: 3,4-diphenyl-3-cyclobutene-1,2-dione；Diphenylcyclobutenedione
• CAS: 24234-76-2
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: WRLLWXGPZKAASP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 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：

  3,4-diphenylcyclobut-3-ene-1,2-dione 以 苯 为溶剂， 以98%的产率得到二苯基乙炔
  参考文献：
  名称：

  Solution-spray flash vacuum pyrolysis: a new method for the synthesis of linear poliynes with odd numbers of C.tplbond.C bonds from substituted 3,4-dialkynyl-3-cyclobutene-1,2-diones

  摘要：

  We report a new method for the preparation of a wide range of linear poliynes, 1a-1i, with an odd number of C = C bonds. This method is based on solution-spray flash vacuum pyrolysis (SS-FVP) of the readily available 3,4-dialkynyl-3-cyclobutene-1,2-diones 3a-3i. It allows the synthesis of multigram quantities of a series of hexatriynes and decapentaynes from poorly volatile and thermally unstable precursors that cannot be subjected to conventional flash vacuum pyrolysis. Yields of the linear poliynes range from 42 to 99%. Similarly, the dodecahexayne 1j was obtained in 31% yield by SS-FVP of the bis(3-cyclobutene-1,2-dione) 3j. The synthesis of the new 3,4-dialkynyl-3-cyclobutene-1,2-diones 3h-3j via the ketals 7, 10, and 13 is reported. The X-ray crystal structure of 1,10-diphenyl-1,3,5,7,9-decapentayne (1c) was solved, and the crystal packing structure provides valuable information to explain the thermal polymerization behavior observed for this compound in the crystalline state.

  DOI：

  10.1021/ja00018a035
• 作为产物：
  描述：

  3-苯基环丁-3-烯-1,2-二酮 在 三氯化铝 、 溴 作用下， 以 四氯化碳 为溶剂， 生成 3,4-diphenylcyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Ried,W.; Schaefer,D.P., Chemische Berichte, 1969, vol. 102, p. 4193 - 4198

  摘要：

  DOI：

文献信息

• Silver Catalyzed Decarbonylative [3 + 2] Cycloaddition of Cyclobutenediones and Formamides
  作者：Pengcheng Wang、Ruirui Yu、Sajjad Ali、Zhengshen Wang、Zhigang Liu、Jinming Gao、Huaiji Zheng

  DOI：10.3390/molecules26102974

  日期：——

  As an important moiety in natural products, N,O-acetal has attracted wide attention in the past few years. An efficient method to construct N,O-acetal has been developed. Using silver catalyst, cyclobutenediones were smoothly converted to the corresponding γ-aminobutenolides in the presence of formamides, in which cyclobutenediones likely proceed with a key decarbonylative [3 + 2] cycloaddition process. In this way, a series of products with varied substituents were isolated in moderate yield and fully characterized.

  作为天然产物中的重要部分，N,O-缩醛在过去几年中引起了广泛关注。已经开发出了一种构建N,O-缩醛的高效方法。在银催化剂的作用下，环丁烯二酮可以顺利转化为相应的γ-氨基丁醇内酯，存在甲酰胺的情况下，其中环丁烯二酮可能通过关键的脱羰基[3 + 2]环加成过程进行。通过这种方式，一系列带有不同取代基的产物以中等产率分离并完全表征。
• Substituent Effects in Mechanochemical Allowed and Forbidden Cyclobutene Ring-Opening Reactions
  作者：Cameron L. Brown、Brandon H. Bowser、Jan Meisner、Tatiana B. Kouznetsova、Stefan Seritan、Todd J. Martinez、Stephen L. Craig

  DOI：10.1021/jacs.0c12088

  日期：2021.3.17

  powerful Maxwell demon could seize a molecule of cyclobutene at its methylene groups and tear it open in a disrotatory fashion to obtain butadiene (Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry. Angew. Chem., Int. Ed. 1969, 8, 781–853). Nearly 40 years later, that demon was discovered, and the field of covalent polymer mechanochemistry was born. In the decade since our demon was befriended

  伍德沃德和霍夫曼曾经开玩笑说，一个非常强大的麦克斯韦恶魔可以抓住一个环丁烯分子的亚甲基，并以旋转方式将其撕开以获得丁二烯（伍德沃德，RB；霍夫曼，R. 轨道对称性的守恒。Angew. Chem 。，诠释。埃德。1969，8, 781–853)。近 40 年后，那个恶魔被发现，共价聚合物机械化学领域诞生了。自从我们的恶魔成为朋友以来的十年里，已经进行了许多基础研究，以建立我们对电环开环反应的力修饰途径的理解。在这里，我们试图通过结合单分子力谱 (SMFS) 和计算来探索环丁烯 (CBE) 和苯并环丁烯 (BCB) 的允许和禁止开环反应中的取代基效应来扩展这一基本理解。我们表明，虽然在SMFS实验的时间尺度上，顺式-BCB的禁止开环发生的力低于反式BCB允许开环的力，但顺式却相反。- 和反-CBE。这种反应性翻转是通过计算分析和对所谓的允许/禁止间隙的讨论来解释的。
• [EN] NEW INDOLE COMPOUNDS HAVING ANTIPROTOZOAL ACTIVITY AND ITS USE AS WELL AS METHODS FOR PRODUCING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS D'INDOLE AYANT UNE ACTIVITÉ ANTIPROTOZOAIRE, LEUR UTILISATION ET PROCÉDÉS POUR LES PRODUIRE
  申请人：UNIV BRAUNSCHWEIG TECH

  公开号：WO2017008826A1

  公开（公告）日：2017-01-19

  In a first aspect, the present invention relates to new compounds as depicted in formula (I). In particular, compounds according to the present invention are bisindolylcyclobuten-dione-based structures having antiprotozoal activity. In a further aspect, pharmaceutical compositions containing the same are provided as well as the use of the compounds and pharmaceutical compositions for the prophylaxis and treatment of parasite based diseases including malaria. Finally, methods for the treatment of parasite diseases including malaria are provided.

  在第一个方面，本发明涉及新化合物，如公式（I）所示。具体来说，根据本发明的化合物是具有抗原虫活性的双吲哚基环丁二酮结构。在另一个方面，还提供含有这些化合物的药物组合物，以及用于预防和治疗包括疟疾在内的寄生虫性疾病的化合物和药物组合物的用途。最后，提供了治疗包括疟疾在内的寄生虫病的方法。
• Generation of 1,2-Bisketenes from Cyclobutene-1,2-diones by Flash Photolysis and Ring Closure Kinetics¹^a
  作者：Annette D. Allen、Jim D. Colomvakos、François Diederich、Ian Egle、Xiaokuai Hao、Ronghua Liu、Janusz Lusztyk、Jihai Ma、Michael A. McAllister、Yves Rubin、Kuangsen Sung、Thomas T. Tidwell、Brian D. Wagner

  DOI：10.1021/ja9722685

  日期：1997.12.17

  The bisketenes 2 have been generated by flash photolysis, and the kinetics of their conversion to 1 have been studied by time-resolved infrared and ultraviolet spectroscopy. The rate constants of the ring closure of 2 are correlated by the ketene stabilization parameters (SE) and with calculated barriers. The rate constant of ring closure of the di-tert-butyl bisketene 2g to cyclobutenedione 1g is

  环丁烯-1,2-二酮 (1) 和 1,2-双烯酮 (RCCO)2 (2) 的相互转化已针对不同的取代基组合 R = H、Me、t-Bu、Ph、Me3Si、CN、 Cl、Br、R1O、炔基和PhS。双烯酮 2 是通过闪光光解产生的，并且通过时间分辨红外和紫外光谱研究了它们转化为 1 的动力学。2 的闭环速率常数与乙烯酮稳定参数 (SE) 和计算的势垒相关。二叔丁基双烯酮 2g 至环丁烯二酮 1g 的闭环速率常数仅比二甲基类似物小 40 倍，显示出相当适中的空间位阻。quinoketene 2s 的闭环速度很快，但没有根据计算的几何和热力学因素预期的那么快。
• Synthesis and characterization of cyclobutenedione–bithiophene π-conjugated polymers: acetal-protecting strategy for Kumada–Tamao–Corriu coupling polymerization between aryl bromide and Grignard reagents
  作者：Tomoyuki Ohishi、Takuma Sone、Kohei Oda、Akihiro Yokoyama

  DOI：10.1039/c9ra08275a

  日期：——

  Kumada–Tamao–Corriu coupling polymerization of a cyclobutenedione monomer whose carbonyl groups are protected as acetals was achieved. Hydrolysis of the acetals afforded donor–acceptor type π-conjugated polymers consisting of cyclobutenedione as an acceptor unit and bithiophene as a donor unit. The acetal-protected monomer was also subjected to Suzuki–Miyaura coupling polymerization. The absorption and emission

  环丁烯二酮是一种芳香环，具有很强的吸电子性能，但容易与亲核试剂发生不希望的反应。在此，实现了羰基被保护为缩醛的环丁烯二酮单体的 Kumada-Tamao-Corriu 偶联聚合。缩醛的水解提供了由环丁烯二酮作为受体单元和二噻吩作为供体单元组成的供体-受体型π-共轭聚合物。缩醛保护的单体也进行了 Suzuki-Miyaura 偶联聚合。与乙缩醛保护的聚合物相比，去保护聚合物的吸收和发射光谱向更长的波长移动。