2-(methyloxidoimino)-1-phenylethanone | 140160-43-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(methyloxidoimino)-1-phenylethanone
• 英文别名: 2-(methyl-oxy-imino)-1-phenyl-ethanone；N-methyl-2-oxo-2-phenylethanimine oxide
• CAS: 140160-43-6
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: VVZJHWOIIJKQLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(methyloxidoimino)-1-phenylethanone 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-methyl-6ξ-phenyl-(3ar,6ac)-hexahydro-pyrrolo[3,4-c]isoxazole
  参考文献：
  名称：

  Black,D.S.C. et al., Australian Journal of Chemistry, 1978, vol. 31, p. 2013 - 2022

  摘要：

  DOI：

文献信息

• Formal Methylene Insertion into the C–H Bond of <i>α</i>-Carbonyl Aldonitrones with Dimethylsulfoxonium Methylide
  作者：Takanobu Sakurai、Tohru Yano、Takuya Suga、Takahiro Soeta、Yutaka Ukaji

  DOI：10.1246/bcsj.20220212

  日期：2022.11.15

  A methylene group was introduced into the C–H bond of α-carbonyl aldonitrones by the reaction with dimethylsulfoxonium methylide, producing one-carbon homologated C-methyl ketonitrones. This formal methylene insertion was applied to one-pot synthesis of quaternary C3-methyl isoxazolidines via successive 1,3-dipolar cycloaddition with alkenes bearing an electron withdrawing group.

  通过与二甲基亚砜鎓反应将亚甲基引入α-羰基醛固酮的 C-H 键，生成单碳同系C-甲基酮硝酮。这种形式的亚甲基插入通过连续的 1,3-偶极环加成与带有吸电子基团的烯烃进行一锅合成季 C3-甲基异恶唑烷。
• Self-Catalyzed Mannich-Type Reaction of Enolizable Cyclic 1,3-Dicarbonyls to Acyclic Nitrones: An Entry to Functionalized β-Enamino Diones
  作者：Massimiliano Cordaro、Francesco Risitano、Angela Scala、Antonio Rescifina、Ugo Chiacchio、Giovanni Grassi

  DOI：10.1021/jo400331b

  日期：2013.4.19

  A new method for the preparation of highly functionalized beta-enamino diones has been developed. The protocol involves an initial self-catalyzed Mannich-type reaction of enolizable cyclic 1,3-dicarbonyls to nitrones, followed by a spontaneous intramolecular reorganization of the resulting nonisolated hydroxylamine to enamino derivatives. These compounds retain the features of unnatural a-amino acids. The ease of preparation makes them attractive intermediates for the synthesis of peptidomimetics, polyheterocycles, and other multifunctional compounds. All experimental results have been efficiently rationalized by in silico studies at the M06-2X level of theory, and a valid mechanistic pathway has been proposed.