thieno[3,4-c]pyrrole-4,6-dione | 6007-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: thieno[3,4-c]pyrrole-4,6-dione
• 英文别名: Thieno[3,4-c]pyrrol-4,6-dion
• CAS: 6007-82-5
• 化学式: C₆H₃NO₂S
• 分子量: 153.161
• InChiKey: GKTQKQTXHNUFSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thieno[3,4-c]pyrrole-4,6-dione 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1,3-二溴-5-辛基-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
  参考文献：
  名称：

  由噻吩二羧酸直接形成酰亚胺可扩大噻吩并吡咯二酮的侧链选择范围

  摘要：

  噻吩并吡咯烷酮（TPD）的合成已更新，以减少合成步骤，去除有害和有毒的试剂，减少副产物废物的量以及在不必要时减少溶剂的使用。可能进行多种功能化，引入16个实例，产率从34％到95％。已证明该反应方案对于噻吩酰亚胺是通用的，并且对有机电子应用中经常使用的TPD受体进行了更深入的侧链工程研究。

  DOI：

  10.1021/acs.orglett.6b03830
• 作为产物：
  描述：

  3,4-噻吩二羧酸 在 ammonium hydroxide 作用下， 以 水 为溶剂， 以76%的产率得到thieno[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  由噻吩二羧酸直接形成酰亚胺可扩大噻吩并吡咯二酮的侧链选择范围

  摘要：

  噻吩并吡咯烷酮（TPD）的合成已更新，以减少合成步骤，去除有害和有毒的试剂，减少副产物废物的量以及在不必要时减少溶剂的使用。可能进行多种功能化，引入16个实例，产率从34％到95％。已证明该反应方案对于噻吩酰亚胺是通用的，并且对有机电子应用中经常使用的TPD受体进行了更深入的侧链工程研究。

  DOI：

  10.1021/acs.orglett.6b03830

文献信息

• 5H-THIOENO(3,4-c)PYRROLE-4,6-DIONE DERIVATIVES AND THEIR USE AS TUMOR NECROSIS FACTOR INHIBITORS
  申请人：ZHANG Hesheng

  公开号：US20080176900A1

  公开（公告）日：2008-07-24

  Taught are derivatives of 5H-thioeno(3,4- c )pyrrole-4,6-dione, their organic, and inorganic salts, methods of synthesis of these derivatives, and their application as active pharmaceutical-ingredients useful as inhibitors of TNFα, the derivative being represented by the general formula (I): in which R 1 represents H, C 1-6 alkyl, OR 4 , OC(O)R 5 , NO 2 , NHC(O)R 6 , or NR 7 R 8 ; R 2 represents H, a halogen, or C 1-6 alkyl; R 3 represents H, methyl, isopropyl, allyl, benzyl, CH 2 CO 2 (C 1-6 alkyl), or CH 2 (CH 2 ) n R 9 ; R 4 , R 5 , R 6 , R 7 , and R 8 each independently and at each occurrence represents H, or C 1-6 alkyl; R 9 represents H, C 1-6 alkyl, OH, OC 1-6 alkyl, NH 2 , NHC 1-6 alkyl, N(C 1-6 alkyl) 2 , or CO 2 (C 1-6 alkyl); and n represents 1, 2, 3, or 4.

  本发明涉及5H-噻烯[3,4-c]吡咯-4,6-二酮的衍生物，它们的有机盐和无机盐，这些衍生物的合成方法，以及它们作为抑制TNFα的活性药物成分的应用，所述衍生物由通式(I)表示： 其中R1代表H，C1-6烷基，OR4，OC(O)R5，NO2，NHC(O)R6或NR7R8；R2代表H，卤素或C1-6烷基；R3代表H，甲基，异丙基，烯丙基，苄基，CH2CO2(C1-6烷基)或CH2(CH2)nR9；R4、R5、R6、R7和R8每个独立地并且在每次出现时代表H或C1-6烷基；R9代表H，C1-6烷基，OH，OC1-6烷基，NH2，NHC1-6烷基，N(C1-6烷基)2或CO2(C1-6烷基)；n代表1、2、3或4。
• [EN] INDACEN-4-ONE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND POLYMERS CONTAINING THEM<br/>[FR] DÉRIVÉS D'INDACÉN-4-ONE, PROCÉDÉ POUR LES PRÉPARER ET POLYMÈRES LES CONTENANT
  申请人：ENI SPA

  公开号：WO2016180988A1

  公开（公告）日：2016-11-17

  Indacen-4-one derivative having general formula (I) in which: - W and W1, which are the same or different, preferably the same, represent an oxygen atom; a sulfur atom; an N-R3 group in which R3 represents a hydrogen atom, or is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups; - Z and Y, which are the same or different, preferably the same, represent a nitrogen atom; or a C-R4 group in which R4 represents a hydrogen atom, or is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, linear or branched C1-C20, preferably C2-C10, alkoxyl groups, R5-O-[CH2-CH2-O]n- polyethyleneoxyl groups in which R5 is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, and n is an integer ranging from 1 to 4; -R6-OR7 groups in which R6 is selected from linear or branched C1-C20, preferably C2-C10, alkylene groups and R7 represents a hydrogen atom or is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, or is selected from R5-[-OCH2-CH2-]n- polyethyleneoxyl groups in which R5 has the same meanings as above reported and n is an integer ranging from 1 to 4, -COR8 groups in which R8 is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, -COOR9 groups in which R9 is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, or represent a -CHO group, or a cyano group (-CN); - R1 and R2, which are the same or different, preferably the same, are selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, linear or branched C1-C20, preferably C2-C10, alkoxyl groups, R5-O-[CH2-CH2-O]n- polyethyleneoxyl groups in which R5 has the same meanings as above reported and n is an integer ranging from 1 to 4, -R6-OR7 groups in which R6 and R7 have the same meanings as above reported, -COR8 groups in which R8 has the same meanings as above reported, -COOR9 groups in which R9 has the same meanings as above reported, or represent a -CHO group, or a cyano group (-CN). Said indacen-4-one derivative may advantageously be used in the synthesis of electron-donor polymers, said polymers being a further object of the present invention. Said polymers may advantageously be used in the construction of photovoltaic devices (or solar devices) such as, for example, photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), on either a rigid or flexible support.

  Indacen-4-one衍生物具有通式（I），其中：- W和W1，相同或不同，最好相同，表示氧原子；硫原子；N-R3基团，其中R3表示氢原子，或从线性或支链C1-C20，最好C2-C10，烷基基团中选择；- Z和Y，相同或不同，最好相同，表示氮原子；或C-R4基团，其中R4表示氢原子，或从线性或支链C1-C20，最好C2-C10，烷基基团，可选地取代的环烷基基团，可选地取代的芳基基团，可选地取代的杂芳基团，线性或支链C1-C20，最好C2-C10，烷氧基基团，R5-O-[CH2-CH2-O]n-聚乙烯氧基基团，其中R5从线性或支链C1-C20，最好C2-C10，烷基基团中选择，n是一个范围从1到4的整数；-R6-OR7基团，其中R6从线性或支链C1-C20，最好C2-C10，烷基基团中选择，R7表示氢原子，或从线性或支链C1-C20，最好C2-C10，烷基基团中选择，或从R5-[-OCH2-CH2-]n-聚乙烯氧基基团中选择，其中R5的含义与上述相同，n是一个范围从1到4的整数，-COR8基团，其中R8从线性或支链C1-C20，最好C2-C10，烷基基团中选择，-COOR9基团，其中R9从线性或支链C1-C20，最好C2-C10，烷基基团中选择，或表示-CHO基团，或氰基团（-CN）；- R1和R2，相同或不同，最好相同，从线性或支链C1-C20，最好C2-C10，烷基基团中选择，可选地取代的环烷基基团，可选地取代的芳基基团，可选地取代的杂芳基团，线性或支链C1-C20，最好C2-C10，烷氧基基团，R5-O-[CH2-CH2-O]n-聚乙烯氧基基团，其中R5的含义与上述相同，n是一个范围从1到4的整数，-R6-OR7基团，其中R6和R7的含义与上述相同，-COR8基团，其中R8的含义与上述相同，-COOR9基团，其中R9的含义与上述相同，或表示-CHO基团，或氰基团（-CN）。所述的indacen-4-one衍生物可以有利地用于合成电子供体聚合物，所述聚合物是本发明的另一个对象。所述聚合物可以有利地用于构建光伏器件（或太阳能器件），例如光伏电池（或太阳能电池），光伏模块（或太阳能模块），在刚性或柔性支撑上。
• [EN] THIENO, FURO AND SELENOPHENO-[3,4-C]PYRROLE-4,6-DIONE COPOLYMERS<br/>[FR] COPOLYMÈRES DE THIÉNO, FURO ET SÉLÉNOPHÉNO-[3,4-C]PYRROLE-4,6-DIONE
  申请人：UNIV LAVAL

  公开号：WO2014029014A1

  公开（公告）日：2014-02-27

  Novel photoactive copolymers based on thieno, furo or selenopheno-[3,4- c]pyrrole-4,6-dione-derivative are described herein. More specifically, the photoactive copolymers comprise repeating units of Formula I -[A1-A2]- I wherein A1 is an electron donating unit such as a mono or polycyclic heteroaryl that is unsubstitued or substituted with one or more C1-20-alkyl or C1-20-alkoxy; and A2 is an alkylfuro or alkylselenopheno-[3,4-c]pyrrole-4,6-dione-derivative. The photoactive copolymers are suitable for use in BHJ solar cells.

  本文描述了基于噻吩、呋喃或硒噻吩-[3,4-c]吡咯烷-4,6-二酮衍生物的新型光活性共聚物。更具体地说，这些光活性共聚物包括式I-[A1-A2]-I中的重复单元，其中A1是一个电子给体单元，比如一个未取代或取代一个或多个C1-20烷基或C1-20烷氧基的单环或多环杂环烯基；A2是一个烷基呋喃或烷基硒噻吩-[3,4-c]吡咯烷-4,6-二酮衍生物。这些光活性共聚物适用于BHJ太阳能电池的使用。
• Oligomeric Perylene Diimide Non-Fullerene Acceptors via Direct (Hetero)Arylation Cross-Coupling Reactions
  申请人：UTI Limited Partnership

  公开号：US20200083457A1

  公开（公告）日：2020-03-12

  Oligomeric compounds useful as organic conjugated materials in electronic devices. Oligomeric compounds contain three or more or four or more of certain PDI units bonded to an organic core. The organic core contains one, two or more thiophene rings. The organic core can contain two or more thiophene rings separated by a linker group; two or more thiophene rings directly fused to each other or indirectly fused to each other through an optionally substituted aromatic or non-aromatic carbocylic ring system or an optionally substituted aromatic heterocyclic or non-aromatic heterocyclic ring system; or each of two or more thiophene rings is fused to an aromatic or non-aromatic carbocylic ring system or an aromatic heterocyclic or non-aromatic heterocyclic ring system and the resulting fused rings containing a thiophene ring are each separated by a linker group M. Methods for making oligomeric compounds by direct heteroarylation are provided.

  富含有机共轭材料的寡聚化合物在电子器件中有用。 寡聚化合物包含与有机核心结合的三个或三个以上或四个或四个以上的某些PDI单元。 有机核心含有一个、两个或更多噻吩环。 有机核心可以包含由连接基团分隔的两个或更多噻吩环； 直接融合在一起的两个或更多噻吩环或通过可选择地取代的芳香或非芳香碳环系统或可选择地取代的芳香杂环或非芳香杂环系统间接融合在一起； 或者两个或更多噻吩环中的每个都与芳香或非芳香碳环系统或芳香杂环或非芳香杂环系统融合，而包含噻吩环的结果融合环之间由连接基团M分隔。 提供了通过直接杂芳基化制备寡聚化合物的方法。
• SEMICONDUCTING POLYMERS AND TERNARY BLENDS THEREOF
  申请人：THE UNIVERSITY OF CHICAGO

  公开号：US20160204348A1

  公开（公告）日：2016-07-14

  Semiconducting photovoltaic polymers and compositions are disclosed. The polymers and compositions exhibit increased power conversion efficiency in solar cells and other applications.

  本发明公开了半导体光伏聚合物和组合物。这些聚合物和组合物在太阳能电池和其他应用中表现出更高的功率转换效率。