2-amino-4-(4-chlorophenyl)-1,3-thiazole-5-carboxaldehyde | 1206796-73-7

• 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-amino-4-(4-chlorophenyl)-1,3-thiazole-5-carboxaldehyde
• 英文别名: 2-Amino-4-(4-chlorophenyl)-1,3-thiazole-5-carbaldehyde
• CAS: 1206796-73-7
• 化学式: C₁₀H₇ClN₂OS
• 分子量: 238.697
• InChiKey: MJMHPZQVIHTPMR-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C(Solvent: Ethyl acetate)
• 沸点：
  463.6±35.0 °C(predicted)
• 密度：
  1.461±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-amino-4-(4-chlorophenyl)-1,3-thiazole-5-carboxaldehyde 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 以87%的产率得到[(2-amino-4-(4-chlorophenyl)-1,3-thiazol-5-yl)methylene]methane-1,1-dicarbonitrile
  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-[(1E)-1-aza-2-(dimethylamino)vinyl]-4-(4-chlorophenyl)-1,3-thiazole-5-carboxaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以86%的产率得到2-amino-4-(4-chlorophenyl)-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

文献信息

• Silica-supported sodium carbonate: an efficient heterogeneous catalyst for the synthesis of new thiazolopyrimidine derivatives
  作者：Priya D. Gavhane、Shuddhodan N. Kadam、Ajay N. Ambhore、Bhaskar S. Dawane

  DOI：10.1007/s11164-021-04508-5

  日期：2021.10

  Herein we describe a new convenient strategy for the synthesis of substituted thiazolopyrimidines. The present approach delivers the use of silica-supported sodium carbonate (SSC) as a recyclable heterogeneous catalyst in PEG- 400 solvent. The described synthetic route offers an easy access for the synthesis of titled compounds through green chemistry protocols. Graphic abstract

  在这里，我们描述了一种新的方便的合成取代噻唑并嘧啶的策略。本方法提供了使用二氧化硅负载的碳酸钠(SSC)作为PEG-400溶剂中的可回收多相催化剂。所描述的合成路线为通过绿色化学方案合成标题化合物提供了一种方便的途径。 图形摘要