(R)-(+)-methyl 2-carbamoyl-2-(5-methyl-2-nitrophenoxy)propanoate | 208342-07-8

• 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: (R)-(+)-methyl 2-carbamoyl-2-(5-methyl-2-nitrophenoxy)propanoate
• CAS: 208342-07-8
• 化学式: C₁₂H₁₄N₂O₆
• 分子量: 282.253
• InChiKey: QYCKKFKDEFORJP-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121.76
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-methyl 2-carbamoyl-2-(5-methyl-2-nitrophenoxy)propanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (2R)-2,7-dimethyl-3-oxo-4H-1,4-benzoxazine-2-carboxamide
  参考文献：
  名称：

  Enantioselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxamides

  摘要：

  Enantiomers of 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxamides bearing different substituents in the aromatic ring are obtained by the cyclization of (R)-monomethyl 2-methyl-2-(2-nitrophenoxy)malonates with the participation of the carboxy and methoxycarbonyl group, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00082-2
• 作为产物：
  描述：

  (R)-2-Methyl-2-(5-methyl-2-nitro-phenoxy)-malonic acid monomethyl ester 在 氨 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 (R)-(+)-methyl 2-carbamoyl-2-(5-methyl-2-nitrophenoxy)propanoate
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acids, -carboxylates and -carboxamides

  摘要：

  (R)-Monomethyl 2-methyl-2-(2- nitrophenoxy)malonates obtained by PLE catalyzed hydrolysis of the corresponding dimethyl malonates undergo solvent-dependent enantioselective cyclization to afford (R)-methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-hentoxazine-2-carboxylates and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxyIic acids, respectively. These compounds are easily converted to enantiomerically and diastereomerically pure carboxamides, which are used as peptidomimetic building blocks. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00485-6