2-氧代-2H-苯并吡喃-3-硫代甲酰胺 | 69015-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 2-氧代-2H-苯并吡喃-3-硫代甲酰胺
• 英文名称: 2-oxo-2H-chromene-3-carbothioamide
• 英文别名: coumarin-3-thiocarboxamide；2-oxochromene-3-carbothioamide
• CAS: 69015-65-2
• 化学式: C₁₀H₇NO₂S
• mdl: MFCD00488459
• 分子量: 205.237
• InChiKey: NNHJYDSWYAVKNK-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  419.5±55.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  2-氧代-2H-苯并吡喃-3-硫代甲酰胺 在 叔丁胺氢溴酸盐 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 spiro (3-amino-2,2,4-tricyano-cyclob-2-enyl)-1,2'-(4'-amino-10'b(H)-N-phenyl-1',3'-dithiano(5,4-c)coumarin)
  参考文献：
  名称：

  NEW SYNTHETIC APPROACHES TO CONDENSED AND SPIRO COUMARINS: COUMARIN-3-THIOCARBOXAMIDE AS BUILDING BLOCK FOR THE SYNTHESIS OF CONDENSED AND SPIRO COUMARINS

  摘要：

  Coumarin-3-thiocarboxamide 1 was reacted with malononitrile, cyanoacetamide or cyanothioacetamide to give the corresponding thiopyrano(3,4-c)coumarin-1-carbonitrile 2. Also, compound 1 was reacted with a variety of active methylenes having an alpha-cyano or alpha-keto group to give thiopyranocoumarin derivatives 3-9. The reaction of compound 1 with different ketene N,S-acetals, afforded the corresponding thiazino(5,4c)coumarin derivatives 10,13 and 16. On reacting compound 10 or 13 with malononitrile, spiro pyran-4,2'-thiazino(5,4-c)coumarin 11 or 14 were obtained, while the reaction of compound 16 with malononitrile gave spiro cyclobutene-1,2'-thiazino(5,4-c)coumarin derivative 17. Treating of compounds 10, 13 or 16 with cyclohexylidenemalononitrile afforded spiro naphthyl-1,2'-tkiazino(5,4-c) coumarin derivatives 12,15 or 18 respectively. Treatment of compound I with CS2 and malononitrile under PTC condition afforded 1,3-dithiano(5,4-c) coumarin derivative 19, which in turn reacted with malononitrile or cyclohexylidenemalononitrile to afford spiro cyclobut-2-enyl-1,2'-(1,3)dithiano(5,4-c)coumarin 20 and spiro naphthyl-1,'2-(1,3)dithiano(5,4-c)coumarin 21 derivatives, respectively.

  DOI：

  10.1080/10426500008043675
• 作为产物：
  描述：

  2-imino-2H-chromene-3-thiocarboxamide 在 盐酸 作用下， 以 乙醇 为溶剂， 以66%的产率得到2-氧代-2H-苯并吡喃-3-硫代甲酰胺
  参考文献：
  名称：

  Activated Nitriles in Heterocyclic Synthesis. Novel Synthesis of 5-Imino-5H-[1]benzopyrano[3,4-c]pyridine-4(3H)-thiones and Their Oxo Analogues

  摘要：

  通过将氰硫基乙酰胺或氰基乙酰胺与水杨醛在酮类或活化腈类存在下，与乙酸铵进行缩合反应，制备了多种苯并吡喃并[3,4-c]吡啶-4(3H)-硫酮衍生物及其氧化类似物。

  DOI：

  10.1246/bcsj.63.1230

文献信息

• Design, synthesis, molecular docking and biological screening of N-ethyl-N-methylbenzenesulfonamide derivatives as effective antimicrobial and antiproliferative agents
  作者：Shimaa M. Abd El-Gilil

  DOI：10.1016/j.molstruc.2019.04.048

  日期：2019.10

  their cytotoxic activity against two different human cell lines, alveolar adenocarcinoma carcinoma (lung) (A-549) and liver carcinoma (HepG2) and antimicrobial. Compound 8 having imidazo[2,1-b]thiazole moiety exhibited the most potent cytotoxic activity against (A-549) cell line (SI; 30.77). While, compound 11 having 2-cyanomethyl thiazole moiety showed significant cytotoxic activity against (HepG2)

  摘要 磺胺类药物是最著名的药物，已被用于制备有效的抗增殖剂。因此，本文描述了具有各种生物活性部分的新系列 N-乙基-N-甲基苯磺酰胺衍生物的合成，例如噻唑 3、4、11、12、14、15、21、1,3,4-噻二嗪 6 , 咪唑 [2,1-b] 噻唑 8、2-氧代-2H-色烯 17 和 3-氧代-3H-苯并[f] 色烯 19，以 4-(2-溴乙酰基)-N-乙基-N 开始-甲基苯磺酰胺 (2)，由 4-乙酰基-N-乙基-N-甲基苯磺酰胺 (1) 与溴在二恶烷/二乙醚混合物中搅拌下相互作用合成。通过元素分析和光谱数据证明了新结构。然而，他们还筛选了它们对两种不同人类细胞系的细胞毒活性，肺泡腺癌（肺）（A-549）和肝癌（HepG2）和抗菌素。具有咪唑并[2,1-b]噻唑部分的化合物8对(A-549)细胞系(SI；30.77)表现出最有效的细胞毒活性。同时，具有 2-氰基甲基噻唑部分的化合物 11
• REACTIONS OF HYDRAZONOYL HALIDES 39¹: SYNTHESIS OF SOME NEW TRIAZOLES AND 2,3-DIHYDRO-1,3,4-THIADIAZOLES
  作者：Abdou O. Abdelhamid、Ali A. Al-Atoom

  DOI：10.1080/10426500490475067

  日期：2004.11.1

  C-acyl-N-phenyllhydrazonoyl halides 1a–ghave been caused to react with 3-(aminomethylthiomethyl)-2H-chromen-2-one in the presence of triethylamine to give triazoles. Also, C-acyl-N-pyrazolylhydrazonoyl chlorides 13a, breact with alkyl carbodithioates (14or 15) a–mafforded 2,3-dihydro-1,3,4-thiadiazoles in good yields. Structures of the new compounds were elucidated on the basis of elemental analyses

  在三乙胺的存在下，C-酰基-N-苯基腙酰卤 1a-g 已与 3-(氨基甲硫基甲基)-2H-chromen-2-one 反应生成三唑。此外，C-酰基-N-吡唑基腙酰氯 13a 与烷基碳二硫代酸酯（14 或 15）a 反应，以良好的收率得到 2,3-二氢-1,3,4-噻二唑。新化合物的结构是在元素分析、光谱数据和其他可能的合成方法的基础上阐明的。
• A New Pathway to 3-Hetaryl-2-oxo-2H-chromenes: On the Proposed Mechanisms for the Reaction of 3-Carbamoyl-2-iminochromenes with Dinucleophiles
  作者：Sergiy Kovalenko、Igor Bylov、Konstantyn Sytnik、Valentyn Chernykh、Yaroslav Bilokin

  DOI：10.3390/51001146

  日期：——

  The present account summarizes the author's studies to elucidate the mechanisms of the recently reported rearrangements resulting from inter- and/or intramolecular reactions of 2-imino-2H-chromene-3-carboxamides with different dinucleophiles.

  本报告总结了作者的研究，以阐明最近报道的由 2-亚氨基-2H-色烯-3-甲酰胺与不同双亲核试剂的分子间和/或分子内反应引起的重排机制。
• Ensembles of rings with a coumarin unit 1. Synthesis of 3-(2-R-thiazol-4-yl)-and 3-(4-R-thiazol-2-yl)coumarins
  作者：Ya. V. Belokon'、S. N. Kovalenko、A. V. Silin、V. M. Nikitchenko

  DOI：10.1007/bf02290865

  日期：1997.10
• Synthesis of 2-(4′-Morpholin-4″-yl-5H-chromeno-[2,3-d]pyrimidin-2′-yl)phenol from salicylaldehyde and substituted acrylonitriles
  作者：V. D. Dyachenko、Yu. Yu. Pugach

  DOI：10.1134/s1070363212050209

  日期：2012.5

  The synthesis of 2-(4'-morpholin-4aEuro(3)-yl-5H-chromeno[2,3-d]pyrimidin-2'-yl)phenol was performed via the reaction of salicylaldehyde with the substituted acrylonitriles. Its structure was confirmed by the X-ray analysis.