(4R,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carbonitrile | 1338695-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carbonitrile
• CAS: 1338695-81-0
• 化学式: C₅H₆N₂O₂
• 分子量: 126.115
• InChiKey: ARAWCPZJIFHWDN-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲苯磺酰氰 、 (R)-5-methyloxazolidin-2-one 在 二苯甲酮 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以83%的产率得到(4R,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carbonitrile
  参考文献：
  名称：

  Photochemically Induced Radical Transformation of C(sp³)–H Bonds to C(sp³)–CN Bonds

  摘要：

  A general protocol for direct transformation of unreactive C(sp(3))-H bonds to C(sp(3))-CN bonds has been developed. The C-H activation was effected by photoexcited benzophenone, and the generated carbon radical was subsequently trapped with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology Is widely applicable to versatile starting materials and, thus, serves as a powerful tool for selective one-carbon elongation for construction of architecturally complex molecules.

  DOI：

  10.1021/ol202659e

文献信息

• Photochemically Induced Radical Transformation of C(sp³)–H Bonds to C(sp³)–CN Bonds
  作者：Shin Kamijo、Tamaki Hoshikawa、Masayuki Inoue

  DOI：10.1021/ol202659e

  日期：2011.11.4

  A general protocol for direct transformation of unreactive C(sp(3))-H bonds to C(sp(3))-CN bonds has been developed. The C-H activation was effected by photoexcited benzophenone, and the generated carbon radical was subsequently trapped with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology Is widely applicable to versatile starting materials and, thus, serves as a powerful tool for selective one-carbon elongation for construction of architecturally complex molecules.