3-methyl-6-bromo-thieno[3,2-b]-thiophene-2-carboxylic acid ethyl ester | 926011-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 3-methyl-6-bromo-thieno[3,2-b]-thiophene-2-carboxylic acid ethyl ester
• 英文别名: ethyl 6-bromo-3-methylthieno[3,2-b]thiophene-2-carboxylate；6-bromo-3-methyl-ethylthieno[3,2-b]thiophene-2-carboxylate；ethyl 3-bromo-6-methylthieno[3,2-b]thiophene-5-carboxylate
• CAS: 926011-52-1
• 化学式: C₁₀H₉BrO₂S₂
• 分子量: 305.216
• InChiKey: STARULUFHBXCOO-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C(Solv: methanol (67-56-1))
• 沸点：
  377.9±37.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-6-bromo-thieno[3,2-b]-thiophene-2-carboxylic acid ethyl ester 在 copper(l) iodide 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 水 、 三乙胺 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 C₁₁H₈N₂O₂S₂
  参考文献：
  名称：

  Thieno[3,2-b]thiophene-2-carboxylic acid derivatives as GPR35 agonists

  摘要：

  The optimization of a series of thieno[3,2-b]thiophene-2-carboxylic acid derivatives for agonist activity against the GPR35 is reported. Compounds were optimized to achieve beta-arrestin-biased agonism for developing probe molecules that may be useful for elucidating the biology and physiology of GPR35. Compound 13 was identified to the most potent GPR35 agonist, and compounds 30 and 36 exhibited the highest efficacy to cause beta-arrestin translocation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.057
• 作为产物：
  描述：

  1-(3,4-二溴-2-噻吩)-1-乙酮 、 巯基乙酸乙酯 在 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到3-methyl-6-bromo-thieno[3,2-b]-thiophene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  含多达七个环的烷基取代的熔融噻吩的合成与结构

  摘要：

  我们已经建立了一系列合成方法来合成烷基取代的稠合噻吩，其稠合度为两个到七个环。这些稠合的噻吩环化合物在常见的有机溶剂中具有非常好的溶解性，使得这些化合物的溶液加工成为电子应用成为可能。与它们的烃类对应物相比，这些稠合噻吩的紫外线吸收发生了蓝移。带隙越大，稳定性越好。3,6-didecanyldithieno [2,3- d：2'，3'- d '] thieno [3,2- b：4,5- b '']二噻吩（FT5）的单晶X射线结果3,7-二癸基噻吩并[3,2- b ]噻吩并[2'，3'：4,5]噻吩并[2,3- d]噻吩（FT4）证明这两种化合物均形成π堆积结构，而不是人字形的堆积图案。这种更有利的π堆叠结构可以导致更好的材料电子性能，例如在用这些化合物制造的器件中的迁移率。

  DOI：

  10.1021/jo061853y

文献信息

• COMPOSITIONS AND METHODS FOR THE TREATMENT OF PATHOLOGICAL CONDITION(S) RELATED TO GPR35 AND/OR GPR35-HERG COMPLEX
  申请人：Deng Huayun

  公开号：US20120022116A1

  公开（公告）日：2012-01-26

  Disclosed are compositions and methods for the prevention and/or treatment of diseases which are pathophysiologically related to GPR35, and/or GPR35-hERG signaling complex. For example, disclosed are compounds for preventing and/or treating diseases which are pathophysiologically related to GPR35 in a subject. The compounds having a formula (I), (II) or (III):

  揭示了与GPR35及/或GPR35-hERG信号复合物在病理生理上相关的疾病的预防和/或治疗的组合物和方法。例如，揭示了用于预防和/或治疗与GPR35在受试者中病理生理相关的疾病的化合物。这些化合物具有以下公式(I)、(II)或(III)：
• Organic semiconductor polymer having liquid crystal properties, organic active layer, organic thin film transistor, and electronic device including the same, and methods of fabricating the same
  申请人：Lee Eun Kyung

  公开号：US20080283828A1

  公开（公告）日：2008-11-20

  Example embodiments relate to an organic semiconductor polymer, in which fused thiophenes having liquid crystal properties and aromatic compounds having N-type semiconductor properties are alternately included in the main chain of the polymer, an organic active layer, an organic thin film transistor (OTFT), and an electronic device including the same, and methods of preparing the organic semiconductor polymer, and fabricating the organic active layer, the OTFT and the electronic device using the same. This organic semiconductor polymer has improved organic solvent solubility, processability, and thin film properties, and may impart increased charge mobility and decreased off-state leakage current when applied to the channel layer of the organic thin film transistor.

  实施例涉及一种有机半导体聚合物，其中在聚合物的主链中交替包含具有液晶性质的融合噻吩和具有N型半导体性质的芳香族化合物，以及包括该聚合物的有机活性层，有机薄膜晶体管（OTFT）和电子器件，以及使用该聚合物制备有机半导体聚合物，制备有机活性层，OTFT和电子器件的方法。该有机半导体聚合物具有改善的有机溶剂溶解性、加工性和薄膜性能，并且当应用于有机薄膜晶体管的通道层时，可以赋予增加的电荷迁移率和减少的关断漏电流。
• FUSED THIOPHENES AS DUAL INHIBITORS OF EGFR/VEGFR AND THEIR USE IN THE TREATMENT OF CANCER
  申请人：Deng Huayun

  公开号：US20120295965A1

  公开（公告）日：2012-11-22

  Disclosed are compositions and methods related to identification of modulators of EGFR and VEGFR.

  本发明涉及识别EGFR和VEGFR的调节剂的组合物和方法。
• FUSED THIOPHENES AND METHODS FOR MAKING AND USING SAME
  申请人：Corning Incorporated

  公开号：US20130281707A1

  公开（公告）日：2013-10-24

  Disclosed are compounds having one of the following formulae: wherein X is an aromatic nucleophilic substitution leaving group; R 1 is hydrogen, an alkyl group, or an aryl group; and Q 1 is a carboxyl protecting group or an aldehyde protecting group. Also disclosed are fused thiophenes that can be prepared using these compounds, as well as stannylthio-containing thiophene, thienothiophene, and dithienothiophene compounds that can be used to prepare fused thiophenes. Methods for making and using the aforementioned compounds, fused thiophenes, and stannylthio-containing thiophene, thienothiophene, and dithienothiophene compounds are also disclosed.

  本发明涉及具有以下公式之一的化合物：其中，X是芳香族亲核取代离子；R1是氢、烷基或芳基；Q1是羧酸保护基或醛保护基。本发明还涉及可使用这些化合物制备的融合噻吩，以及可用于制备融合噻吩的含锡硫基噻吩、噻吩噻吩和二噻吩噻吩化合物。本发明还涉及制备和使用上述化合物、融合噻吩和含锡硫基噻吩、噻吩噻吩和二噻吩噻吩化合物的方法。
• Discovery of 2-(4-Methylfuran-2(5<i>H</i>)-ylidene)malononitrile and Thieno[3,2-<i>b</i>]thiophene-2-carboxylic Acid Derivatives as G Protein-Coupled Receptor 35 (GPR35) Agonists
  作者：Huayun Deng、Haibei Hu、Mingqian He、Jieyu Hu、Weijun Niu、Ann M. Ferrie、Ye Fang

  DOI：10.1021/jm200999f

  日期：2011.10.27

  Screening with dynamic mass redistribution (DMR) assays in a native cell line HT-29 led to identification of two novel series of chemical compounds, 2-(4-methylfuran-2(5H)-ylidene)malononitrile and thieno[3,2-b]thiophene-2-carboxylic. acid derivatives, as GPR35 agonists. Of these, 2-(3-cyano-5-(3,4-dichlorophenyl)-4,5-dimethylfuran-2(5H)-ylidene)malononitrile (YE120) and 6-bromo-3-methylthieno[3,2-b]thiophene-2-carboxylic acid (YE210) were found to be the two most potent GPR35 agonists with an EC50 of 32.5 +/- 1.7 nM and 63.7 +/- 4.1 nM, respectively. Both agonists exhibited better potency than that of zaprinast, a known GPR35 agonist. DMR antagonist assays, knockdown of GPR35 with interference RNA, receptor internalization assays, and Tango beta-arrestin translocation assays confirmed that the agonist activity of these ligands is specific to GPR35. The present study provides novel chemical series as a starting point for further investigations of GPR35 biology and pharmacology.