2-[(1E)-1-aza-2-(dimethylamino)vinyl]-4-phenyl-1,3-thiazole-5-carboxaldehyde | 1210051-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(1E)-1-aza-2-(dimethylamino)vinyl]-4-phenyl-1,3-thiazole-5-carboxaldehyde
• 英文别名: N'-(5-formyl-4-phenyl-1,3-thiazol-2-yl)-N,N-dimethylmethanimidamide
• CAS: 1210051-67-4
• 化学式: C₁₃H₁₃N₃OS
• 分子量: 259.332
• InChiKey: HIEOPBZFJWFUPT-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(1E)-1-aza-2-(dimethylamino)vinyl]-4-phenyl-1,3-thiazole-5-carboxaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以87%的产率得到2-amino-4-phenyl-1,3-thiazole-5-carboxaldehyde
  参考文献：
  名称：

  Synthesis, Characterization, and Biological Activity of Substituted Thiazole-5-carboxaldehydes and Their Ylidenenitriles Derivatives

  摘要：

  The Vilsmeier-Haack reaction of 2-amino -4-(4-substituted phenyl)-thiazoles 1, in the presence of micellar media, gives formylated derivatives 2, which upon hydrolysis afforded thiazole-5-carboxaldehydes 3. Microwave-assisted Knoevenagel condensation of 3 with active methylene compounds, in the presence of piperidine as catalyst, gives excellent yields of ylidenenitrile compounds 4. The structures of the newly synthesized compounds were established on the basis of elemental analysis, IR, H-1 NMR, and C-13 NMR spectral analysis. All newly synthesized compounds were screened for antibacterial activity using two Gram-positive and one Gram-negative bacterial species and their antifungal activity was screened using two fungal species.

  DOI：

  10.1080/10426500802583520
• 作为产物：
  描述：

  2-氨基-4-苯基噻唑 、 N,N-二甲基甲酰胺 在 sodium dodecyl-sulfate 、 三氯氧磷 作用下， 生成 2-[(1E)-1-aza-2-(dimethylamino)vinyl]-4-phenyl-1,3-thiazole-5-carboxaldehyde
  参考文献：
  名称：

  N-保护2-氨基-4-苯基噻唑化合物的甲酰化反应

  摘要：

  研究了4-苯基-NN'-苯甲酰基和4-苯基-N-取代（N-磺酰基和N-苯基）-2-氨基噻唑分子与POCl 3 /DMF的Vilsmeier Haack甲酰化反应。晶体(6) ((E) -N' - (5-甲酰基-4-苯基噻唑-2-基)-N ,N-二甲基甲酰亚胺酰胺)和晶体(14) ( N-苯基-N- (4-苯基噻唑) -2-基)甲酰胺)分子是在NN'苯甲酰基、N-磺酰基保护基4-苯基噻唑分子的甲酰化反应中得到的。在N-苯基取代的噻唑类化合物，在胺基上加成醛基取代噻唑环，形成N-苯基-N- (4-苯基噻唑-2-基)甲酰胺分子。所有化合物均已合成并通过 FT-IR、1 H-NMR、13 C-NMR 技术和 X 射线结构分析进行了表征。这些分子展示了 O,S-syn 构象。

  DOI：

  10.1016/j.molstruc.2023.135840

文献信息

• BAHAR, M. H.;SABATA, B. K., INDIAN J. CHEM., 1981, 20, N 4, 328-329
  作者：BAHAR, M. H.、SABATA, B. K.

  DOI：——

  日期：——
• Synthesis, Characterization, and Biological Activity of Substituted Thiazole-5-carboxaldehydes and Their Ylidenenitriles Derivatives
  作者：Nilesh J. Thumar、Manish P. Patel

  DOI：10.1080/10426500802583520

  日期：2009.10.13

  The Vilsmeier-Haack reaction of 2-amino -4-(4-substituted phenyl)-thiazoles 1, in the presence of micellar media, gives formylated derivatives 2, which upon hydrolysis afforded thiazole-5-carboxaldehydes 3. Microwave-assisted Knoevenagel condensation of 3 with active methylene compounds, in the presence of piperidine as catalyst, gives excellent yields of ylidenenitrile compounds 4. The structures of the newly synthesized compounds were established on the basis of elemental analysis, IR, H-1 NMR, and C-13 NMR spectral analysis. All newly synthesized compounds were screened for antibacterial activity using two Gram-positive and one Gram-negative bacterial species and their antifungal activity was screened using two fungal species.
• Formylation reactions of N-protecting 2-Amino-4-phenyl thiazole compounds
  作者：Abdullah Biçer、Ramazan Altundaş

  DOI：10.1016/j.molstruc.2023.135840

  日期：2023.10

  (14) (N-phenyl-N-(4-phenylthiazol-2-yl)formamide) molecules were obtained in the formylating reactions of N-N' benzoyl, N-sulphonyl protecting group 4-phenyl thiazole molecules. In the N-phenyl substituted thiazole compound, an aldehyde functional group is added to the amine group instead of the thiazole ring to form the N-phenyl-N-(4-phenylthiazol-2-yl)formamide molecule. All compounds have been synthesized

  研究了4-苯基-NN'-苯甲酰基和4-苯基-N-取代（N-磺酰基和N-苯基）-2-氨基噻唑分子与POCl 3 /DMF的Vilsmeier Haack甲酰化反应。晶体(6) ((E) -N' - (5-甲酰基-4-苯基噻唑-2-基)-N ,N-二甲基甲酰亚胺酰胺)和晶体(14) ( N-苯基-N- (4-苯基噻唑) -2-基)甲酰胺)分子是在NN'苯甲酰基、N-磺酰基保护基4-苯基噻唑分子的甲酰化反应中得到的。在N-苯基取代的噻唑类化合物，在胺基上加成醛基取代噻唑环，形成N-苯基-N- (4-苯基噻唑-2-基)甲酰胺分子。所有化合物均已合成并通过 FT-IR、1 H-NMR、13 C-NMR 技术和 X 射线结构分析进行了表征。这些分子展示了 O,S-syn 构象。