3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione | 343341-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione
• 英文别名: 3,4-bis(2,5-dimethylthiophen-3-yl)furan-2,5-dione
• CAS: 343341-43-5
• 化学式: C₁₆H₁₄O₃S₂
• 分子量: 318.417
• InChiKey: DAQQUGSMPZABCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione 在 乙酸铵 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以90%的产率得到3,4-bis(2,5-dimethyl-3-thienyl)pyrrole-2,5-dione
  参考文献：
  名称：

  摘要：

  A new convenient procedure for the synthesis of photochromic N-alkyldithienylmaleimides was developed on the basis of the reaction of 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione with primary amines. Photochromic properties of the products were examined.

  DOI：

  10.1023/a:1021612131447
• 作为产物：
  描述：

  3,4-bis(2,5-dimethylthiophen-3-yl)cyclobut-3-ene-1,2-dione 生成 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione
  参考文献：
  名称：

  Synthesis and Photochromism of Dihetarylethenes and Spiro Compounds based on Thiophene Derivatives

  摘要：

  Different types of diarylethenes bearing thiophene derivatives were synthesized by a short way and its photchromic properties were examined. It has been demonstrated for the first time that the photochromism of diarylcyclobutenediones depends on aryl substituents and dithienylcyclobutenediones in contrast to the annulated thiophene derivatives of cyclobutenedione, do not exhibit photochromic properties. An efficient approach for the synthesis of spiro compounds of the thieno[3,2-b]pyrrole series was developed starting from easily accessible substituted thienylhydrazine.

  DOI：

  10.1080/15421400590946703

文献信息

• Synthesis of 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione from mucobromic acid
  作者：S. V. Shorunov、F. M. Stoyanovich、M. M. Krayushkin

  DOI：10.1007/s11172-005-0126-6

  日期：2004.10

  Palladium-catalyzed cross-coupling between 2,5-dimethyl-3-thienylboronic and mucobromic acids under phase transfer catalysis (PTC) conditions gave the expected 3,4-bis(2,5-dimethyl-3-thienyl)-5-hydroxyfuran-2-one in 32% yield. The by-product was 2,2’,5,5’-tetramethyl-3,3’-bithiophene. The oxidation of the obtained hemiacylal with potassium permanganate under PTC conditions afforded 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione in high yield.

  在相转移催化（PTC）条件下，使用钯催化剂进行的2,5-二甲基-3-噻吩基硼酸与黏溴酸的交叉偶联反应生成了预期的3,4-双(2,5-二甲基-3-噻吩基)-5-羟基呋喃-2-酮，产率为32%。副产物为2,2’,5,5’-四甲基-3,3’-联噻吩。在PTC条件下，使用高锰酸钾氧化所得的半缩醛，以高产率合成了3,4-双(2,5-二甲基-3-噻吩基)呋喃-2,5-二酮。
• [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。
• The mechanodonor-acceptor coupling (MDAC) approach for unidirectional multi-state fluorochromism
  作者：Luyan Gu、Lujia Zhang、Xiao Luo、Ying Zheng、Zhiwei Ye、Meng Lv、Jinquan Chen、Chunlai Chen、Yi Xiao、Weihong Zhu、Xuhong Qian、Youjun Yang

  DOI：10.1007/s11426-020-9874-6

  日期：2021.2

  Uni-directional multi-state fluorochromic scaffolds are valuable photofunctional molecules and yet scarce. We report a general approach for their design, i.e., mechanodonor-acceptor coupling (MDAC). A photochromic molecule is a mechanodonor, due to its capability to convert photonic energy into mechanical force. Upon proper coupling, it can be used to drive a mechanochromic molecule for uni-directional multi-state fluorochromism. The embodiment of this approach is a rhodamine-dithienylethylene hydride (RDH), which has been successfully employed in super-resolution localization microscopy

  单向多态荧光变色支架是有价值的光功能分子，但非常稀缺。我们报告了一种通用的设计方法，即机械供体-受体耦合（MDAC）。光致变色分子作为机械供体，因其能够将光能转化为机械力。通过适当的耦合，它可以驱动一个机械变色分子，实现单向多态荧光变色。这种方法的具体实例是罗丹明-二噻烯乙烯氢化物（RDH），已成功应用于超分辨率定位显微镜技术。
• Synthesis and photochromic properties of dithienylmaleimides with sulfur-containing fragments
  作者：O. Yu. Kuznetsova、I. V. Platonova、B. V. Lichitskii、M. M. Krayushkin、V. A. Barachevskii

  DOI：10.1007/s11172-012-0295-z

  日期：2012.11

  A number of sulfur-containing dithienylmaleimide derivatives were synthesized. Spectral and kinetic characteristics of the compounds obtained were studied, which showed that all the dithienylethenes synthesized possessed photochromic properties.

  合成了多种含硫二噻吩马来酰亚胺衍生物。对所得化合物的光谱和动力学特性进行了研究，结果表明合成的所有二噻吩乙烯均具有光致变色性能。
• Synthesis of thienyl-containing photochromes (dithienylethenes, fulgides, fulgimides, and spirocompounds)
  作者：Mikhail M. Krayushkin、Valery A. Barachevsky、Masahiro Irie

  DOI：10.1002/hc.20334

  日期：2007.7

  © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:557–567, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20334

  © 2007 Wiley Periodicals, Inc. 杂原子化学 18:557–567, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20334