methyl 2-(1-(N-(prop-2-ynyl)acetamido)butyl)thiazole-4-carboxylate | 1585992-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(1-(N-(prop-2-ynyl)acetamido)butyl)thiazole-4-carboxylate
• CAS: 1585992-82-0
• 化学式: C₁₄H₁₈N₂O₃S
• 分子量: 294.375
• InChiKey: QPPVSMDKPHBKOD-UHFFFAOYSA-N

物化性质

• 沸点：
  413.1±35.0 °C(predicted)
• 密度：
  1.190±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.5
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-(二甲氨基)-2-异氰基丙烯酸甲酯 、 正丁醛 、 炔丙胺 、 硫代乙酸 在 Porcine Pancreas Lipase 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到methyl 2-(1-(N-(prop-2-ynyl)acetamido)butyl)thiazole-4-carboxylate
  参考文献：
  名称：

  A Novel One-Pot Multicomponent Enzymatic Synthesis of 2,4-Disubstituted Thiazoles

  摘要：

  A novel one-pot multicomponent synthetic method of some new 2,4-disubstituted thiazoles catalyzed by enzyme was developed. Lipase from porcine pancreas (PPL) displayed good catalytic activity to promote this reaction starting from amines, aldehyde, thioacetic acid and methyl 3-(dimethyl amino)-2-isocyanoacrylate under mild conditions (35 A degrees C) with good yields (up to 93 %). The experimental results revealed PPL showed broad catalytic activity to substrates. The blank and control experiments revealed that PPL played important catalytic role during the process. All the new compounds were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. This PPL-catalyzed one-pot multicomponent synthetic method provided a new strategy to synthesize 2,4-disubstituted thiazoles and expanded the application of enzymes in organic synthesis.

  DOI：

  10.1007/s10562-014-1229-1