4-bromo-2-(2-methyl-1,3-dioxolan-2-yl)thiazole | 1037747-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-bromo-2-(2-methyl-1,3-dioxolan-2-yl)thiazole
• CAS: 1037747-43-5
• 化学式: C₇H₈BrNO₂S
• 分子量: 250.116
• InChiKey: PFNDPVNNYOVPCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  31.35
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(2-methyl-1,3-dioxolan-2-yl)thiazole 、 Tert-butyl 2-[2-chloro-6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate 在 正丁基锂 、 三丁基氯化锡 、 四(三苯基膦)钯 作用下， 以 乙醚 、 1,4-二氧六环 为溶剂， 反应 12.25h， 以110 mg的产率得到
  参考文献：
  名称：

  Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics

  摘要：

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.

  DOI：

  10.1021/ol801035c
• 作为产物：
  描述：

  乙二醇 、 2-乙酰基-4-溴噻唑 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以75%的产率得到4-bromo-2-(2-methyl-1,3-dioxolan-2-yl)thiazole
  参考文献：
  名称：

  Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics

  摘要：

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.

  DOI：

  10.1021/ol801035c