4-methyl-7-oxo-6-phenyl-5,6-diazaspiro[2.4]hept-4-ene 5-oxide | 1119304-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4-methyl-7-oxo-6-phenyl-5,6-diazaspiro[2.4]hept-4-ene 5-oxide
• 英文别名: 4-Methyl-5-oxido-6-phenyl-6-aza-5-azoniaspiro[2.4]hept-4-en-7-one；4-methyl-5-oxido-6-phenyl-6-aza-5-azoniaspiro[2.4]hept-4-en-7-one
• CAS: 1119304-84-5
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: MYQUMCRRNDTYAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(1-(hydroxyimino)ethyl)-N-phenylcyclopropanecarboxamide 在 三氟乙酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到4-methyl-7-oxo-6-phenyl-5,6-diazaspiro[2.4]hept-4-ene 5-oxide
  参考文献：
  名称：

  PIFA-Mediated Oxidative Cyclization of 1-Carbamoyl-1-oximylcycloalkanes: Synthesis of Spiro-Fused Pyrazolin-5-one N-Oxides

  摘要：

  A convenient and efficient synthesis of spiro-fused pyrazolin-5-one N-oxides starting from readily available 1-carbamoyl-1-oximylcycloalkanes is developed. This general protocol features a novel and facile way for access to the five-membered azaheterocycles by formation of a new N-N single bond. The key cyclization step utilizes the formation of an N-oxonitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its subsequent intramolecular trapping by the amide moiety under rather mild experimental conditions.

  DOI：

  10.1021/ol802952e

文献信息

• PIFA-Mediated Oxidative Cyclization of 1-Carbamoyl-1-oximylcycloalkanes: Synthesis of Spiro-Fused Pyrazolin-5-one <i>N</i>-Oxides
  作者：Kewei Wang、Xiaolan Fu、Jinying Liu、Yongjiu Liang、Dewen Dong

  DOI：10.1021/ol802952e

  日期：2009.2.19

  A convenient and efficient synthesis of spiro-fused pyrazolin-5-one N-oxides starting from readily available 1-carbamoyl-1-oximylcycloalkanes is developed. This general protocol features a novel and facile way for access to the five-membered azaheterocycles by formation of a new N-N single bond. The key cyclization step utilizes the formation of an N-oxonitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its subsequent intramolecular trapping by the amide moiety under rather mild experimental conditions.