ethyl N-pyrimidin-5-yloxyacetimidate | 1236291-58-9

• 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: ethyl N-pyrimidin-5-yloxyacetimidate
• CAS: 1236291-58-9
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: UMATWAHEVNXKKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.71
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙酰羟肟酸乙酯 、 (4'-methoxyphenyl)(pyridin-3-yl)iodonium triflate 在 sodium t-butanolate 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以81%的产率得到ethyl N-pyrimidin-5-yloxyacetimidate
  参考文献：
  名称：

  Metal-Free One-Pot Synthesis of Benzofurans

  摘要：

  AbstractEthyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition‐metal‐free conditions. The obtained O‐arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]‐rearrangement, and cyclization in a fast and operationally simple one‐pot fashion without using excess reagents. Alternatively, the O‐arylated products could be isolated or transformed in situ to aryloxyamines or O‐arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)‐machaeriol B.

  DOI：

  10.1002/chem.201403523

文献信息

• Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of <i>O</i>-Arylhydroxylamines and Substituted Benzofurans
  作者：Thomas J. Maimone、Stephen L. Buchwald

  DOI：10.1021/ja1044874

  日期：2010.7.28

  An efficient Pd catalyst for the O-arylation of ethyl acetohydroximate with aryl chlorides, bromides, and iodides has been developed. Ethyl acetohydroximate serves as an efficient hydroxylamine equivalent for C-O cross-coupling, thereby allowing for the preparation of O-arylhydroxylamines from simple aryl halides. Short reaction times and broad substrate scope, including heteroaryl coupling partners, allow access to O-arylhydroxylamines that would be difficult to prepare in a single step by traditional methods. Moreover, the O-arylated products so formed can be directly transformed into substituted benzofurans in a single operation.