(S)-4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (S)-4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S)-4-methyl-2,3-dihydro-1,4-benzoxazine-2-carboxylate
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: PTWGOHJFPUZGII-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-N-甲基苯胺 在 racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl 、 palladium diacetate 、 potassium phosphate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 94.0h， 生成 (S)-4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular C−O Bond Formation

  摘要：

  A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands. The reaction proceeds under mild conditions using weak bases such as Cs2CO3 or K3PO4. A variety of functional groups are tolerated in the reaction. and enantioenriched alcohols can be coupled without erosion of optical purity. The mildness of the reaction conditions allows for the use of polyfunctionalized substrates. This method was used as the key step in the synthesis of MKC-242, an antidepressant currently in clinical trials. The synthesis of MKC-242 was achieved in 40% overall yield from commercially available sesamol and acrylonitrile,

  DOI：

  10.1021/ja012046d