(S)-(+)-6-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid | 222625-25-4

• 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)-(+)-6-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
• 英文别名: (2S)-6-methoxy-2-methyl-3-oxo-4H-1,4-benzoxazine-2-carboxylic acid
• CAS: 222625-25-4
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: QBZKSLSKPUYYBP-NSHDSACASA-N

物化性质

• 沸点：
  475.3±45.0 °C(predicted)
• 密度：
  1.359±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(+)-6-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 N-<<(2R)-6-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-yl>carbonyl>-D-phenylalanine benzyl ester
  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
• 作为产物：
  描述：

  (R)-2-(4-Methoxy-2-nitro-phenoxy)-2-methyl-malonic acid monomethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 反应 24.0h， 生成 (S)-(+)-6-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
  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

文献信息

• Stereoselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acids, -carboxylates and -carboxamides
  作者：Matej Breznik、Valentina Hrast、Alenka Mrcina、Danijel Kikelj

  DOI：10.1016/s0957-4166(98)00485-6

  日期：1999.1

  (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.