potassium thiophene carboxylate | 33311-43-2

• 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: potassium thiophene carboxylate
• 英文别名: potassium thiophene-2-carboxylate；potassium 2-thiophenecarboxylate；potassium thiophen-2-carboxylate；Potassium thiophenate；potassium;thiophene-2-carboxylate
• CAS: 33311-43-2
• 化学式: C₅H₃O₂S*K
• 分子量: 166.242
• InChiKey: PCZSPVPUWRXJLD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.88
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium thiophene carboxylate 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-噻吩甲酰氯
  参考文献：
  名称：

  Synthesis of heteroaromatic tropeines and heterogeneous binding to glycine receptors

  摘要：

  Heteroaromatic carboxylic esters of (nor) tropine were synthesized. Tropine esters displaced [(3)H]strychnine binding to glycine receptors of rat spinal cord with low Hill slopes. Two-site displacement resulted in nanomolar IC(50,1) and micromolar IC(50,2) values, and IC(50,2)/IC(50,1) ratios up to 615 depending on the heteroaromatic rings and N-methyl substitution. Nortropeines displayed high affinity and low heterogeneity. IC(50,1) and IC(50,2) values of tropeines did not correlate suggesting different binding modes/sites. Glycine potentiated only the nanomolar displacement reflecting positive allosteric interactions and potentiation of ionophore function. Affinities of three (nor) tropeines were different for glycine receptors but identical for 5-HT(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.029
• 作为产物：
  描述：

  2-噻吩甲酸 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 以94%的产率得到potassium thiophene carboxylate
  参考文献：
  名称：

  钯盐与芳基三氟甲磺酸酯的钯催化脱羧偶联合成联芳基和芳基酮

  摘要：

  已开发出一种双金属催化剂体系，该体系首次允许芳基和酰基羧酸盐与芳基三氟甲磺酸酯进行脱羧交叉偶联。与芳基卤化物相反，这些亲电试剂会产生非配位阴离子副产物，这些副产物不会干扰脱羧步骤，而脱羧步骤会导致亲核碳交联伙伴的产生。结果，可用于此转化的羧酸酯底物的范围从邻位取代或其他活化的衍生物扩展到广泛的邻位，间位和对位取代的芳族羧酸盐。优化了两种替代方案，一种方案涉及在存在铜的情况下加热基板I / 1,10-菲咯啉（10–15 mol％）和PdI 2 /膦（2–3 mol％）在NMP中作用1–24 h，另一项涉及Cu I / 1,10–菲咯啉（6–15 mol） ％）和NMP中的PdBr 2 / Tol-BINAP（2 mol％）使用微波加热5-10分钟。尽管大多数产品都可以通过标准加热来获得，但发现微波辐射特别有益于将未活化的羧酸酯与官能化的芳基三氟甲磺酸酯转化。通过48个示例演示了该转换的综合效

  DOI：

  10.1002/chem.200900892

文献信息

• Synthesis of Biaryls and Aryl Ketones<i>via</i>Microwave-Assisted Decarboxylative Cross-Couplings
  作者：Lukas J. Gooßen、Bettina Zimmermann、Christophe Linder、Nuria Rodríguez、Paul P. Lange、Jens Hartung

  DOI：10.1002/adsc.200900337

  日期：2009.11

  A protocol for the microwave-assisted decarboxylative cross-couplings of carboxylic acid salts with aryl halides has been developed that allows the synthesis of various biaryls and aryl ketones in high yields. After careful adaptation of the bimetallic catalyst system and reaction conditions, these mechanistically complex transformations can now be performed within only five minutes in concentrated

  已经开发了用于微波辅助羧酸盐与芳基卤化物的脱羧交叉偶联的方案，该方案允许以高收率合成各种联芳基和芳基酮。在仔细调整了双金属催化剂体系和反应条件之后，这些机理复杂的转化反应现在可以在密封容器中的浓缩溶液中仅五分钟之内完成。这种大大简化的反应方案非常适合并行合成和药物发现中的应用。
• Biaryl and Aryl Ketone Synthesis via Pd-Catalyzed Decarboxylative Coupling of Carboxylate Salts with Aryl Triflates
  作者：Lukas J. Goossen、Christophe Linder、Nuria Rodríguez、Paul P. Lange

  DOI：10.1002/chem.200900892

  日期：2009.9.21

  the first time allows the decarboxylative cross‐coupling of aryl and acyl carboxylates with aryl triflates. In contrast to aryl halides, these electrophiles give rise to non‐coordinating anions as byproducts, which do not interfere with the decarboxylation step that leads to the generation of the carbon nucleophilic cross‐coupling partner. As a result, the scope of carboxylate substrates usable in this

  已开发出一种双金属催化剂体系，该体系首次允许芳基和酰基羧酸盐与芳基三氟甲磺酸酯进行脱羧交叉偶联。与芳基卤化物相反，这些亲电试剂会产生非配位阴离子副产物，这些副产物不会干扰脱羧步骤，而脱羧步骤会导致亲核碳交联伙伴的产生。结果，可用于此转化的羧酸酯底物的范围从邻位取代或其他活化的衍生物扩展到广泛的邻位，间位和对位取代的芳族羧酸盐。优化了两种替代方案，一种方案涉及在存在铜的情况下加热基板I / 1,10-菲咯啉（10–15 mol％）和PdI 2 /膦（2–3 mol％）在NMP中作用1–24 h，另一项涉及Cu I / 1,10–菲咯啉（6–15 mol） ％）和NMP中的PdBr 2 / Tol-BINAP（2 mol％）使用微波加热5-10分钟。尽管大多数产品都可以通过标准加热来获得，但发现微波辐射特别有益于将未活化的羧酸酯与官能化的芳基三氟甲磺酸酯转化。通过48个示例演示了该转换的综合效
• Copper-Catalyzed Decarboxylation of Aromatic Carboxylic Acids: En Route to Milder Reaction Conditions
  作者：Gérard Cahiez、Alban Moyeux、Olivier Gager、Maël Poizat

  DOI：10.1002/adsc.201201018

  日期：2013.3.11

  The copper‐catalyzed decarboxylation of carboxylic aromatic acids has been advantageously achieved by using aliphatic amines like tetramethylethylenediamine (TMEDA) or hexamethylenetetraamine (HMTA) as ligands instead of the aromatic heterocyclic amines (quinoline, phenanthroline) used until now. The improvement is significant since the reaction can be performed at a lower temperature (ca. 50 °C less)

  通过使用脂肪族胺（例如四甲基乙二胺（TMEDA）或六亚甲基四胺（HMTA））作为配体代替目前使用的芳香族杂环胺（喹啉，菲咯啉），可以有利地实现铜催化的羧酸芳族羧酸的脱羧。由于该反应可以在较低的温度（约低50℃）下进行，并且反应时间明显较短（15分钟，而不是12至24小时），因此该改进非常重要。
• Approaching the Integer‐Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross‐Coupling
  作者：Jiang Tian Liu、Hannes Hase、Sarah Taylor、Ingo Salzmann、Pat Forgione

  DOI：10.1002/anie.201914458

  日期：2020.4.27

  A library of symmetrical linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach compared to the existing methods. The modularity

  使用脱羧交叉偶联反应作为关键转化制备了对称的线性低聚噻吩文库。噻吩羧酸钾盐用作交叉偶联伙伴，而无需助催化剂，碱或添加剂。与现有方法相比，该方法显示出完全的化学选择性，是一种更全面的绿色方法。通过制备具有最多10个噻吩重复单元的谨慎的寡聚噻吩，可以证明这种方法的模块化。对称的低聚噻吩是典型的有机半导体，可以通过光谱评估其分子电掺杂随链长的变化。观察到整数电荷转移的低聚噻吩临界长度为10个噻吩单元，
• Anti-leishmanial activity of heteroleptic organometallic Sb(v) compounds
  作者：Muhammad Irshad Ali、Muhammad Khawar Rauf、Amin Badshah、Ish Kumar、Craig M. Forsyth、Peter C. Junk、Lukasz Kedzierski、Philip C. Andrews

  DOI：10.1039/c3dt51382c

  日期：——

  In seeking new drugs for the treatment of the parasitic disease Leishmaniasis, an extensive range of organometallic antimony(V) dicarboxylates of the form [SbR3(O2CR′)2] have been synthesised, characterised and evaluated. The organometallic moieties (R) in the complexes vary in being Ph, tolyl (o, m or p), or benzyl. The carboxylates are predominantly substituted benzoates with some compounds incorporating acetato or cinnamato ligands. The crystal structures of [Sb(p-Tol)3(O2CC6H2-3,4,5-(OMe)3)2]·0.5PhMe and [SbPh3(m-CH3C6H4CH2CO2)2] were determined and shown to adopt a typical trigonal pyramidal geometry, being monomeric with a five coordinate Sb centre. In total, the biological activity of 26 Sb(V) compounds was assessed against the Leishmania major parasite, and also human fibroblast skin cells to give a measure of general toxicity. Of these, 11 compounds (predominantly substituted benzoates with m- or p-tolyl ligands) proved to be highly effective against the parasite amastigotes at concentrations of 0.5–3.5 μM, while being non-toxic towards the mammalian cells at levels below 25 μM, making them highly promising drug candidates.

  在为治疗寄生虫疾病利什曼病寻找新药物的过程中，合成、表征并评估了一系列具有[SbR3(O2CR′)2]形式的金属有机锑(V)二羧酸盐。这些配合物中的金属有机部分（R）包括苯基、甲基苯基（邻、间或对位）或苄基。羧酸盐主要为取代苯甲酸盐，部分化合物包含乙酸根或肉桂酸根配体。测定了[Sb(p-Tol)3(O2CC6H2-3,4,5-(OMe)3)2]·0.5PhMe和[SbPh3(m-CH3C6H4CH2CO2)2]的晶体结构，显示它们采用典型的三角锥几何构型，为单体结构，有五配位的锑中心。总共评估了26种锑(V)化合物的生物活性，针对利什曼原虫Leishmania major以及人类成纤维皮肤细胞，以衡量其普遍毒性。其中，11种化合物（主要是含间位或对位甲基苯基配体的取代苯甲酸盐）在0.5至3.5 μM浓度下对寄生虫的无鞭毛体显示出高度效果，并且在低于25 μM的浓度下对哺乳动物细胞无毒，使其成为极具前景的药物候选物。