4-bromo-2-[5-chloro-2-(methoxymethoxy)phenyl]thiazole | 271601-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-bromo-2-[5-chloro-2-(methoxymethoxy)phenyl]thiazole
• 英文别名: 4-Bromo-2-[5-chloro-2-(methoxymethoxy)phenyl]-1,3-thiazole
• CAS: 271601-01-5
• 化学式: C₁₁H₉BrClNO₂S
• 分子量: 334.621
• InChiKey: GGIBKIKPFNXOGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-2-[5-chloro-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-Chloro-2-(4-phenyl-1,3-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：

  1-氯-4-(甲氧基甲氧基)苯 、 2,4-二溴噻唑 在 叔丁基锂 、 zinc(II) chloride 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 为溶剂， 反应 16.0h， 以62%的产率得到4-bromo-2-[5-chloro-2-(methoxymethoxy)phenyl]thiazole
  参考文献：
  名称：

  2,4-Disubstituted Thiazoles by Regioselective Cross-Coupling or Bromine-Magnesium Exchange Reactions of 2,4-Dibromothiazole

  摘要：

  2,4-二溴噻唑的交叉偶联反应优先发生在更缺电子的 2 位。这一事实可用于制备 2-取代的 4-溴噻唑，作为 2,4-二取代噻唑的前体。本研究提供了区域选择性 Negishi 和 Stille 交叉偶联反应的方案。另外，还可以通过卤素-金属交换反应将标题化合物 2 位金属化。作为对成熟的溴-锂交换反应的补充，介绍了具有区域选择性的溴-镁交换反应。

  DOI：

  10.1055/s-0030-1258373

文献信息

• 2,4-Disubstituted Thiazoles by Regioselective Cross-Coupling or Bromine-Magnesium Exchange Reactions of 2,4-Dibromothiazole
  作者：Thorsten Bach、Stefan Gross、Stefan Heuser、Carolin Ammer、Golo Heckmann

  DOI：10.1055/s-0030-1258373

  日期：2011.1

  Cross-coupling reactions occur on 2,4-dibromothiazole preferentially at the more electron-deficient 2-position. This fact can be favorably used to prepare 2-substituted 4-bromothiazoles, which serve as precursors for 2,4-disubstituted thiazoles. Protocols for regioselective Negishi and Stille cross-coupling reactions are provided. Alternatively, the title compound can be metalated in 2-position by a halogen-metal exchange reaction. As a supplement to the well-established bromine-lithium exchange, the regioselective bromine-magnesium exchange reaction is presented.

  2,4-二溴噻唑的交叉偶联反应优先发生在更缺电子的 2 位。这一事实可用于制备 2-取代的 4-溴噻唑，作为 2,4-二取代噻唑的前体。本研究提供了区域选择性 Negishi 和 Stille 交叉偶联反应的方案。另外，还可以通过卤素-金属交换反应将标题化合物 2 位金属化。作为对成熟的溴-锂交换反应的补充，介绍了具有区域选择性的溴-镁交换反应。
• Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling
  作者：Thorsten Bach、Stefan Heuser

  DOI：10.1016/s0040-4039(00)00018-6

  日期：2000.3

  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.