3-Methyl-4-methyl-5-phenyl-4-oxazolin-2-one | 54026-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methyl-4-methyl-5-phenyl-4-oxazolin-2-one
• 英文别名: 3,4-dimethyl-5-phenyl-3H-oxazol-2-one；2(3H)-Oxazolone, 3,4-dimethyl-5-phenyl-；3,4-dimethyl-5-phenyl-1,3-oxazol-2-one
• CAS: 54026-27-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: ORJYQENMECHTPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Methyl-4-methyl-5-phenyl-4-oxazolin-2-one 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以79%的产率得到(4R,5S)-3,4-dimethyl-5-phenyloxazolidin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of (±)-conhydrine, (±)-ephedrine, and (±)-N-methylephedrine

  摘要：

  DOI：

  10.1016/s0040-4039(00)85960-2
• 作为产物：
  描述：

  4-methyl-5-phenyl-1,3-oxazole 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 3-Methyl-4-methyl-5-phenyl-4-oxazolin-2-one
  参考文献：
  名称：

  On the Reactions of Oxazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1, 4-Oxazin-3-one and Azetidin-2-one Derivatives

  摘要：

  氧杂铵盐(IX)与二烷基酰基膦酸酯(IV)在三乙胺的存在下发生反应，生成了1, 4-氧杂啉-3-酮(XII)和/或氮杂环丁酮衍生物(XIII)。在IXa-b与IVa的反应中，分离出了稳定的反应中间体(Xa-b)。一些产品被确认与通过独立途径合成的真实样品相同。讨论了这一新型反应的机制，包括环扩展和环收缩、取代基对反应性的影响，以及XIII的立体化学。

  DOI：

  10.1248/cpb.22.1526

文献信息

• Reaction of oximes with dimethyl carbonate: a new entry to 3-methyl-4,5-disubstituted-4-oxazolin-2-ones
  作者：C. A. Marques、M. Selva、P. Tundo、F. Montanari

  DOI：10.1021/jo00073a041

  日期：1993.10

  The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190-degrees-C and in the presence of K2CO3 yields 3-methyl-4,5-disubstituted-4-oxazolin-2-ones. The reaction can be applied to both aliphatic and aromatic ketone oximes, provided that a methylene group be present near the C=N bond. Nonoptimized yields range from 22 to 48%. The reaction seems to be a [3,3] sigmatropic rearrangement where DMC plays a key role in causing the initial N-methylation of the oximes.
• Krieg,B.; Konieczny,P., Justus Liebigs Annalen der Chemie, 1976, p. 1862 - 1872
  作者：Krieg,B.、Konieczny,P.

  DOI：——

  日期：——
• Stereoselective synthesis of (±)-conhydrine, (±)-ephedrine, and (±)-N-methylephedrine
  作者：Tatsuya Shono、auYoshihiro Matsumura、Takenobu Kanazawa

  DOI：10.1016/s0040-4039(00)85960-2

  日期：1983.1
• On the Reactions of Oxazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1, 4-Oxazin-3-one and Azetidin-2-one Derivatives
  作者：AKIRA TAKAMIZAWA、HISAO SATO

  DOI：10.1248/cpb.22.1526

  日期：——

  Reaction of Oxazolium salts (IX) with dialkyl acylphosphonates (IV) in the presence of triethylamine afforded 1, 4-oxazin-3-one (XII) and/or azetidin-2-one derivatives (XIII). In the reaction of IXa-b with IVa, stable reaction intermediates (Xa-b) were isolated. Some of the products were confirmed to be identical with authentic samples synthesized by an independent pathway. The mechanism of this novel reaction involving ring expansion and ring contraction, substituent effects on the reactivity, and stereochemistry of XIII are discussed.

  氧杂铵盐(IX)与二烷基酰基膦酸酯(IV)在三乙胺的存在下发生反应，生成了1, 4-氧杂啉-3-酮(XII)和/或氮杂环丁酮衍生物(XIII)。在IXa-b与IVa的反应中，分离出了稳定的反应中间体(Xa-b)。一些产品被确认与通过独立途径合成的真实样品相同。讨论了这一新型反应的机制，包括环扩展和环收缩、取代基对反应性的影响，以及XIII的立体化学。