N-(2-furanylmethyl)-2-thiophenecarboxamide

• 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: N-(2-furanylmethyl)-2-thiophenecarboxamide
• 英文别名: N-(furan-2-ylmethyl)thiophene-2-carboxamide
• 化学式: C₁₀H₉NO₂S
• mdl: MFCD00460916
• 分子量: 207.253
• InChiKey: AUELCNAPLMONQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-furanylmethyl)-2-thiophenecarboxamide 、 T406石油添加剂 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以81%的产率得到N-[(1H-1,2,3-benzotriazol-1-yl)(2-thienyl)methylidene](2-furyl)methanamine
  参考文献：
  名称：

  Efficient Microwave Access to Polysubstituted Amidines from Imidoylbenzotriazoles

  摘要：

  Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a-w gave diversely substituted amidines 7a-Aa in 76-94% yields. Convenient preparations of a variety of amides 5a-Ab (87-96%) and imidoylbenzotriazoles 6a-w (56-95%) have also been developed using microwave irradiation under mild conditions and short reaction times. These results demonstrate further the advantages of microwave synthesis and introduce a new application of imidoylbenzotriazoles in the preparation of polysubstituted amidines.

  DOI：

  10.1021/jo052443x
• 作为产物：
  描述：

  2-噻吩甲酸 在 氯化亚砜 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.17h， 生成 N-(2-furanylmethyl)-2-thiophenecarboxamide
  参考文献：
  名称：

  Efficient Microwave Access to Polysubstituted Amidines from Imidoylbenzotriazoles

  摘要：

  Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a-w gave diversely substituted amidines 7a-Aa in 76-94% yields. Convenient preparations of a variety of amides 5a-Ab (87-96%) and imidoylbenzotriazoles 6a-w (56-95%) have also been developed using microwave irradiation under mild conditions and short reaction times. These results demonstrate further the advantages of microwave synthesis and introduce a new application of imidoylbenzotriazoles in the preparation of polysubstituted amidines.

  DOI：

  10.1021/jo052443x

文献信息

• Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation
  作者：Keyume Ablajan、Long Tian、Qianwei Zhang

  DOI：10.1055/a-1838-9491

  日期：2022.10

  protocol for the amidation of hydrazide with amine has been developed by utilizing I2 as an oxidant under metal- and base-free conditions at room temperature. N-Acylation products of amines were obtained in good to excellent yields without using toxic reagents. This method is operationally straightforward and tolerates aliphatic/aromatic and primary/secondary amines with different hydrazides.

  通过在室温下在无金属和无碱条件下使用 I 2作为氧化剂，开发了一种用于酰肼与胺的酰胺化的有效方案。在不使用有毒试剂的情况下，以良好至极好的收率获得了胺的 N-酰化产物。该方法操作简单，可耐受脂肪族/芳香族和伯/仲胺与不同的酰肼。
• Preparation, structural analysis, bioactivity assessment, enzyme and molecular docking calculations of some furan/thiophene-2-carboxamide derivatives
  作者：Sukriye Cakmak、Semiha Yenigun、Tevfik Ozen

  DOI：10.1007/s13738-023-02852-4

  日期：2023.10

  Some furan/thiophene-2-carboxamide derivatives (1–3) were prepared from acyl chlorides and heterocyclic amine derivatives with good yields, employing synthetic route and their chemical structures were confirmed using different spectroscopic methods including IR, 1H NMR, 13C NMR and elemental analysis. Three different enzyme inhibition effect tests as urease, acetylcholinesterase (AChE) and butyryl

  采用合成路线，以酰氯和杂环胺衍生物为原料，以良好的收率制备了一些呋喃/噻吩-2-甲酰胺衍生物( 1–3 )，并通过IR、 1 H NMR、13 C NMR等不同光谱方法确认了其化学结构和元素分析。对这些化合物进行了脲酶、乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）抑制活性三种不同的酶抑制效果测试。生物学评价结果清楚地表明，化合物1的抗脲酶活性是硫脲标准品的约9.8倍，而化合物3的抗脲酶活性是硫脲标准品的约9.8倍。对 BChE 酶的活性比加兰他敏标准品高约 4.2 倍。通过分子插入模拟研究了每种目标化合物与脲酶、乙酰胆碱酯酶和丁酰胆碱酯酶活性位点的分子相互作用，结果证实了实验结果。结果还表明，带有噻吩/呋喃碳酰胺部分的化合物（例如1和3）可以作为未来开发更有效药剂的有希望的结构。
• Green and Selective Synthesis of<i>N</i>-Substituted Amides using Water Soluble Porphyrazinato Copper(II) Catalyst
  作者：Sara S. E. Ghodsinia、Batool Akhlaghinia、Elham Safaei、Hossein Eshghi

  DOI：10.5935/0103-5053.20130115

  日期：——

  N, N',N '', N '''-Tetramethyl tetra-2,3-pyridinoporphyrazinato copper(II) methyl sulfate ([Cu(2,3-tmtppa)](MeSO4)(4)) efficiently catalyzed the direct conversion of nitriles to N-substituted amides. The one pot selective synthesis of the N-substituted amides from nitriles and primary amines was performed in refluxing H2O. The catalyst was recovered and reused at least four times, maintaining its efficiency.