methyl 2-(4-butylphenyl)-4-methylthiazole-5-carboxylate | 1313711-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(4-butylphenyl)-4-methylthiazole-5-carboxylate
• 英文别名: Methyl 2-(4-butylphenyl)-4-methyl-1,3-thiazole-5-carboxylate
• CAS: 1313711-65-7
• 化学式: C₁₆H₁₉NO₂S
• 分子量: 289.398
• InChiKey: XGTCMQWFALJKJB-UHFFFAOYSA-N

物化性质

• 沸点：
  408.2±47.0 °C(predicted)
• 密度：
  1.124±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-butylphenyl)-4-methylthiazole-5-carboxylate 在 氯化亚砜 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 2-(4-butylphenyl)-4-methylthiazole-5-carbonyl chloride
  参考文献：
  名称：

  An investigation of phenylthiazole antiflaviviral agents

  摘要：

  Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono-or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.041
• 作为产物：
  描述：

  2-氯乙酰乙酸甲酯 、 butylthiobenzamide 以 乙醇 为溶剂， 反应 24.0h， 以92%的产率得到methyl 2-(4-butylphenyl)-4-methylthiazole-5-carboxylate
  参考文献：
  名称：

  An investigation of phenylthiazole antiflaviviral agents

  摘要：

  Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono-or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.041