potassium 3-aminothiophene-2-carboxylate | 1210469-45-6

• 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 3-aminothiophene-2-carboxylate
• 英文别名: 3-Aminothiophene-2-carboxylic acid potassium salt；potassium;3-aminothiophene-2-carboxylate
• CAS: 1210469-45-6
• 化学式: C₅H₄NO₂S*K
• 分子量: 181.257
• InChiKey: BRARFRQWXXCLBB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  10
• 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：
  94.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-溴藜芦醛 、 potassium 3-aminothiophene-2-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 1,10-菲罗啉 、 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以85%的产率得到7,8-dimethoxythieno[3,2-c]isoquinoline
  参考文献：
  名称：

  级联胺化/分子内脱羧偶联合成3 H-吡唑并[3,4- c ]异喹啉和噻吩并[3,2- c ]异喹啉

  摘要：

  为3合成的一般方法ħ -吡唑并[3,4- c ^ ]异喹啉和噻吩并[3,2- C ^ ]异喹啉，描述涉及级联亚胺化/分子内脱羧耦合钾之间2-氨基（杂）的实施苯甲酸酯和2-卤代芳基醛。吡唑基底物的反应需要Pd-Cu双金属系统才能获得更高的收率，而噻吩基的底物仅使用Pd催化剂即可提供优异的收率。

  DOI：

  10.1021/ol4023722
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 生成 potassium 3-aminothiophene-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of thienopyridinones as Chk1 inhibitors

  摘要：

  A series of thienopyridinone derivatives was designed and synthesized as inhibitors of checkpoint kinase 1 (Chk1). Most of them exhibited moderate to good Chk1 inhibitory activities. Among them, compounds 8q, 8t, and 8w with excellent Chk1 inhibitory activities (IC50 values of 4.05, 6.23, and 2.33nM, respectively) displayed strong synergistic effects with melphalan, a DNA-damaging agent in the cell-based assay. Further kinase profiling indicated that compound 8t was highly selective against CDK2/cyclinA, Aurora A, and PKC.

  DOI：

  10.1016/j.bmc.2014.06.044

文献信息

• Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction
  作者：Marie Kissane、Orla A. McNamara、David Mitchell、David M. Coppert、Humphrey A. Moynihan、Kurt T. Lorenz、Anita R. Maguire

  DOI：10.1016/j.tetlet.2011.11.051

  日期：2012.1

  The palladium-catalysed decarboxylative cross-coupling of heterocyclic aromatic carboxylates and aryl halides is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and tetrabutylammonium bromide (TBAB). Utilizing a mixed solvent system consisting of N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP), the cross-coupling system operated at temperatures

  描述了钯催化的杂环芳族羧酸盐和芳基卤化物的脱羧交叉偶联。使用催化性Pd（0）和四丁基溴化铵（TBAB）在相对温和的条件下进行交叉偶联。利用由N，N-二甲基甲酰胺（DMF）和N-甲基-2-吡咯烷酮（NMP）组成的混合溶剂系统，交叉偶联系统在80至140°C的温度范围内运行。
• A Practical Synthesis of Biaryls via a Thermal Decarboxylative Pd-Catalyzed Cross-Coupling Reaction Operating at Moderate Temperature
  作者：David Mitchell、David M. Coppert、Humphrey A. Moynihan、Kurt T. Lorenz、Marie Kissane、Orla A. McNamara、Anita R. Maguire

  DOI：10.1021/op200030t

  日期：2011.9.16

  The palladium-catalyzed decarboxylative cross-coupling of aminothiophene carboxylate and 1-bromo-4-chlorobenzene to produce 3-amino-2-(4-chlorophenyl)thiophene (2) is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and TBAB. Through use of a mixed-solvent system of DMF and NMP, it was possible to operate the cross-coupling system at 80 degrees C. An assessment of carbon dioxide liberation, which provides insight into the reaction operating parameters, is also discussed.
• Synthesis of 3<i>H</i>-Pyrazolo[3,4-<i>c</i>]isoquinolines and Thieno[3,2-<i>c</i>]isoquinolines via Cascade Imination/Intramolecular Decarboxylative Coupling
  作者：Garima Pandey、Subhendu Bhowmik、Sanjay Batra

  DOI：10.1021/ol4023722

  日期：2013.10.4

  A general approach for the synthesis of 3H-pyrazolo[3,4-c]isoquinolines and thieno[3,2-c]isoquinolines is described involving the implementation of a cascade imination/intramolecular decarboxylative coupling between potassium 2-amino(hetero)benzoates and 2-haloarylaldehydes. The reactions of pyrazole-based substrates require a Pd–Cu bimetallic system for superior yields whereas the thienyl-based substrates

  为3合成的一般方法ħ -吡唑并[3,4- c ^ ]异喹啉和噻吩并[3,2- C ^ ]异喹啉，描述涉及级联亚胺化/分子内脱羧耦合钾之间2-氨基（杂）的实施苯甲酸酯和2-卤代芳基醛。吡唑基底物的反应需要Pd-Cu双金属系统才能获得更高的收率，而噻吩基的底物仅使用Pd催化剂即可提供优异的收率。
• Design, synthesis and biological evaluation of thienopyridinones as Chk1 inhibitors
  作者：Pinrao Song、Peng Peng、Mengmeng Han、Xianchao Cao、Xiaodong Ma、Tao Liu、Yubo Zhou、Yongzhou Hu

  DOI：10.1016/j.bmc.2014.06.044

  日期：2014.9

  A series of thienopyridinone derivatives was designed and synthesized as inhibitors of checkpoint kinase 1 (Chk1). Most of them exhibited moderate to good Chk1 inhibitory activities. Among them, compounds 8q, 8t, and 8w with excellent Chk1 inhibitory activities (IC50 values of 4.05, 6.23, and 2.33nM, respectively) displayed strong synergistic effects with melphalan, a DNA-damaging agent in the cell-based assay. Further kinase profiling indicated that compound 8t was highly selective against CDK2/cyclinA, Aurora A, and PKC.