2-(2-氨基-1,3-噻唑-4-基)-1-苯乙酮 | 57626-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(2-氨基-1,3-噻唑-4-基)-1-苯乙酮
• 中文别名: 2,6-二甲基苯酚
• 英文名称: 2-amino-4-phenacylthiazole
• 英文别名: 2-Amino-4-benzoylmethyl-thiazol；2-(2-amino-thiazol-4-yl)-1-phenyl-ethanone；2-(2-Amino-1,3-thiazol-4-yl)-1-phenylethanone
• CAS: 57626-32-1
• 化学式: C₁₁H₁₀N₂OS
• mdl: MFCD02706789
• 分子量: 218.279
• InChiKey: CSNWEDRWWVJFHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-氨基-1,3-噻唑-4-基)-1-苯乙酮 在 盐酸 、 mercury dichloride 、 锌 作用下， 以 水 为溶剂， 反应 24.0h， 生成 4-phenethyl-thiazol-2-ylamine
  参考文献：
  名称：

  Dérivés de l'imidazo[2,1-b]thiazole X. Propriétés fongistatiques de 2-aminothiazoles et de 6-aryl imidazo[2,1-b]thiazoles substitués respectivement en 4 et en 3 par un reste aryléthyle, aroylméthyle, β-hydroxy β-aryléthyle et éthoxycarbonylméthyle

  摘要：

  Several 2-aminothiazoles, substituted in 4 with an ethylacetate, aroylmethyl, beta-hydroxy beta-arylethyl or arylethyl chain, were combined with omega-bromoacetophenones in order to obtain the corresponding 3-substituted 6-arylimidazo[2,1-b]thiazoles to perform fungistatic tests. The ethyl (2-aminothiazole-4-yl) acetates led to the expected imidazothiazoles. This was not noted in the other cases. Thus, the presence of an aroylmethyl residue considerably decrease the reactivity of the aminothiazole. The transformation of the ketonic carbonyl to alcohol II, or even better, to methylene is necessary for the condensation to be effected with omega-bromoacetophenones. The yield of this reaction is low. The results of fungistatic tests show the interest of the aminothiazole derivatives with an aroylmethyl on Candida albicans, Aspergillus fumigatus, Epidermophyton floccosum. The best activity is observed when the phenyl has one or several methyl or methoxy groups. The imidazothiazole compounds, although there is a substitution in 6, show lower efficiency.

  DOI：

  10.1016/0223-5234(90)90192-6
• 作为产物：
  描述：

  4-羟基-1-苯基丁-2-炔-1-酮 在 potassium carbonate 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 2-(2-氨基-1,3-噻唑-4-基)-1-苯乙酮
  参考文献：
  名称：

  炔丙基溴与硫脲/硫代嘧啶酮的多米诺烷基化-环化反应：2-氨基噻唑和 5H-噻唑并[3,2-a]嘧啶-5-酮的简便合成

  摘要：

  2-氨基噻唑和5H-噻唑并[3,2-a]嘧啶-5-酮的新合成被开发为炔丙基溴分别与硫脲和硫代嘧啶酮的多米诺烷基化-环化反应。在微波辐射下进行多米诺骨牌反应，在几分钟内产生所需的化合物，产率高

  DOI：

  10.1055/s-0029-1217700

文献信息

• Robert; Xicluna; Panouse, European Journal of Medicinal Chemistry, 1975, vol. 10, # 1, p. 59 - 64
  作者：Robert、Xicluna、Panouse

  DOI：——

  日期：——
• Dérivés de l'imidazo[2,1-b]thiazole X. Propriétés fongistatiques de 2-aminothiazoles et de 6-aryl imidazo[2,1-b]thiazoles substitués respectivement en 4 et en 3 par un reste aryléthyle, aroylméthyle, β-hydroxy β-aryléthyle et éthoxycarbonylméthyle
  作者：JF Robert、S Boukraa、JJ Panouse、V Loppinet、JP Chaumont

  DOI：10.1016/0223-5234(90)90192-6

  日期：1990.11

  Several 2-aminothiazoles, substituted in 4 with an ethylacetate, aroylmethyl, beta-hydroxy beta-arylethyl or arylethyl chain, were combined with omega-bromoacetophenones in order to obtain the corresponding 3-substituted 6-arylimidazo[2,1-b]thiazoles to perform fungistatic tests. The ethyl (2-aminothiazole-4-yl) acetates led to the expected imidazothiazoles. This was not noted in the other cases. Thus, the presence of an aroylmethyl residue considerably decrease the reactivity of the aminothiazole. The transformation of the ketonic carbonyl to alcohol II, or even better, to methylene is necessary for the condensation to be effected with omega-bromoacetophenones. The yield of this reaction is low. The results of fungistatic tests show the interest of the aminothiazole derivatives with an aroylmethyl on Candida albicans, Aspergillus fumigatus, Epidermophyton floccosum. The best activity is observed when the phenyl has one or several methyl or methoxy groups. The imidazothiazole compounds, although there is a substitution in 6, show lower efficiency.
• ROBERT, J. F.;BOUKRAA, S.;PANOUSE, J. J.;LOPPINET, V.;CHAUMONT, J. P., EUR. J. MED. CHEM., 25,(1990) N, C. 731-736
  作者：ROBERT, J. F.、BOUKRAA, S.、PANOUSE, J. J.、LOPPINET, V.、CHAUMONT, J. P.

  DOI：——

  日期：——
• ROBERT J.-F.; XICLUNA A.; PANOUSE J. J., EUR. J. MED. CHEM., 1975, 10, NO 1, 59-64
  作者：ROBERT J.-F.、 XICLUNA A.、 PANOUSE J. J.

  DOI：——

  日期：——
• Domino Alkylation-Cyclization Reaction of Propargyl Bromides with Thioureas/Thiopyrimidinones: A New Facile Synthesis of 2-Aminothiazoles and 5H-Thiazolo[3,2-a]pyrimidin-5-ones
  作者：Maurizio Botta、Daniele Castagnolo、Mafalda Pagano、Martina Bernardini

  DOI：10.1055/s-0029-1217700

  日期：2009.8

  A new synthesis of 2-aminothiazoles and 5H-thiazolo[3,2-a]pyrimidin-5-ones was developed as a domino alkylation-cyclization reaction of propargyl bromides with thioureas and thio¬pyrimidinones, respectively. Domino reactions were performed under microwave irradiation leading to desired compounds in a few minutes and high yields

  2-氨基噻唑和5H-噻唑并[3,2-a]嘧啶-5-酮的新合成被开发为炔丙基溴分别与硫脲和硫代嘧啶酮的多米诺烷基化-环化反应。在微波辐射下进行多米诺骨牌反应，在几分钟内产生所需的化合物，产率高