Methyl 6-ethenyl-5-(trifluoromethylsulfonyloxy)pyridine-2-carboxylate | 178876-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Methyl 6-ethenyl-5-(trifluoromethylsulfonyloxy)pyridine-2-carboxylate
• CAS: 178876-93-2
• 化学式: C₁₀H₈F₃NO₅S
• 分子量: 311.238
• InChiKey: LHXPNCXLEQIBET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl 6-ethenyl-5-(trifluoromethylsulfonyloxy)pyridine-2-carboxylate 在 chromium(VI) oxide 、 N-溴代丁二酰亚胺(NBS) 、 氢气 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 3.17h， 生成 Methyl 6-(oxiran-2-yl)-5-(trifluoromethylsulfonyloxy)pyridine-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of Dimethyl Sulfomycinamate

  摘要：

  Dimethyl sulfomycinamate (1), a methanolysis product from the natural antibiotic sulfomycin I, is synthesized in 11 steps (Scheme 19). The chemistry of various pyridine, thiazole, and oxazole heterocycles and their coupling reactions under palladium catalysis are examined. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions on doubly activated pyridine 62 and the condensation reaction between bromo ketone 69 and amide 28 to form the oxazole moiety 76. The first preparation of oxazole triflates is described, as are some of their chemical properties.

  DOI：

  10.1021/jo960433d
• 作为产物：
  描述：

  3-羟基-6-甲基吡啶 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium permanganate 、 三氯化铝 、 溴 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 142.08h， 生成 Methyl 6-ethenyl-5-(trifluoromethylsulfonyloxy)pyridine-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of Dimethyl Sulfomycinamate

  摘要：

  Dimethyl sulfomycinamate (1), a methanolysis product from the natural antibiotic sulfomycin I, is synthesized in 11 steps (Scheme 19). The chemistry of various pyridine, thiazole, and oxazole heterocycles and their coupling reactions under palladium catalysis are examined. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions on doubly activated pyridine 62 and the condensation reaction between bromo ketone 69 and amide 28 to form the oxazole moiety 76. The first preparation of oxazole triflates is described, as are some of their chemical properties.

  DOI：

  10.1021/jo960433d

文献信息

• Total Synthesis of Dimethyl Sulfomycinamate
  作者：T. Ross Kelly、Fengrui Lang

  DOI：10.1021/jo960433d

  日期：1996.1.1

  Dimethyl sulfomycinamate (1), a methanolysis product from the natural antibiotic sulfomycin I, is synthesized in 11 steps (Scheme 19). The chemistry of various pyridine, thiazole, and oxazole heterocycles and their coupling reactions under palladium catalysis are examined. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions on doubly activated pyridine 62 and the condensation reaction between bromo ketone 69 and amide 28 to form the oxazole moiety 76. The first preparation of oxazole triflates is described, as are some of their chemical properties.