4-Bromo-2-(5-butoxy-2-methoxymethoxy-phenyl)-thiazole | 271601-04-8

• 英文名称: 4-Bromo-2-(5-butoxy-2-methoxymethoxy-phenyl)-thiazole
• 英文别名: 4-Bromo-2-[5-butoxy-2-(methoxymethoxy)phenyl]-1,3-thiazole
• CAS: 271601-04-8
• 化学式: C₁₅H₁₈BrNO₃S
• 分子量: 372.283
• InChiKey: DEUSNEMYCQLJNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Bromo-2-(5-butoxy-2-methoxymethoxy-phenyl)-thiazole 在 四(三苯基膦)钯 盐酸 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 水 、 苯 为溶剂， 生成 4-Butoxy-2-(4-phenyl-thiazol-2-yl)-phenol
  参考文献：
  名称：

  Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling

  摘要：

  The difunctional substrate 2,4-dibromothiazole 2 was transformed into the title compounds 1 by consecutive Pd(0)-catalyzed cross-coupling reactions. Aryl zinc reagents which were prepared by ortho-lithiation of compounds 3 and subsequent transmetalation were used as carbon nucleophiles in the first coupling reaction. By this means, an aryl substituent was attached to the 2-position (50-62% yield). A succeeding cross-coupling with arylboronic acids 4 occurred at the 4-position of the intermediate 4-bromothiazoles 5 (76-97% yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00018-6
• 作为产物：
  描述：

  2,4-二溴噻唑 、 1-Butoxy-4-methoxymethoxy-benzene 在 bis-triphenylphosphine-palladium(II) chloride 叔丁基锂 、 zinc(II) chloride 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 为溶剂， 以61%的产率得到4-Bromo-2-(5-butoxy-2-methoxymethoxy-phenyl)-thiazole
  参考文献：
  名称：

  Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling

  摘要：

  The difunctional substrate 2,4-dibromothiazole 2 was transformed into the title compounds 1 by consecutive Pd(0)-catalyzed cross-coupling reactions. Aryl zinc reagents which were prepared by ortho-lithiation of compounds 3 and subsequent transmetalation were used as carbon nucleophiles in the first coupling reaction. By this means, an aryl substituent was attached to the 2-position (50-62% yield). A succeeding cross-coupling with arylboronic acids 4 occurred at the 4-position of the intermediate 4-bromothiazoles 5 (76-97% yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00018-6