(S)-(+)-2,6-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid | 222625-22-1

• 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)-(+)-2,6-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
• 英文别名: (2S)-2,6-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid；(2S)-2,6-dimethyl-3-oxo-4H-1,4-benzoxazine-2-carboxylic acid
• CAS: 222625-22-1
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: GRLHKEFUJXAGOA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2,6-dimethyl-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)-2,6-dimethyl-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：

  (2R)-3-methoxy-2-methyl-2-(4-methyl-2-nitrophenoxy)-3-oxopropanoic acid 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 反应 24.0h， 生成 (S)-(+)-2,6-dimethyl-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

• Influence of Chirality of the Preceding Acyl Moiety on the <i>cis</i>/<i>trans</i> Ratio of the Proline Peptide Bond
  作者：Matej Breznik、Simona Golič Grdadolnik、Gerald Giester、Ivan Leban、Danijel Kikelj

  DOI：10.1021/jo0159439

  日期：2001.10.1

  in (1)H NMR spectra. The signals were assigned to trans (72%) and cis (28%) conformers. Crystallographic analysis of 4 showed that only the cis conformation is present in the crystalline state. The (1)H NMR chemical shift pattern of three sets of signals observed in 2 was observed also in benzyl (2S)-1-[(2R/S)-3-methoxy-2-methyl-2-(4-methyl-2-nitrophenoxy)-3-oxopropanoyl]-2-pyrrolidinecarboxylate. (R)-Carboxylic

  我们报道脯氨酸肽键的顺式/反式比可以强烈地受到脯氨酸之前的酰基残基的手性的影响。衍生自（2S）-2,6-二甲基-3-氧代-3,4-二氢-2H-1,4-苯并恶嗪-2-羧酸（8）和（2R）-3-甲氧基-2-的酰基部分酰基-Pro分子中的甲基-2-（4-甲基-2-硝基苯氧基）-3-氧代丙酸（5）影响脯氨酸肽键的异构化，从而将欧米茄二面角限制为反式。（2S）-1-（[[（2S）-2,6-二甲基-3-氧代-3,4-二氢-2H-1,4-苯并恶嗪-2-基]羰基）-2-吡咯烷羧酸酯（ 3）源自2D（1）H NMR构象分析和晶体学数据，仅显示脯氨酸肽键的反式构象。另一方面，含有（R）酰基部分的非对映异构体4在（1）1 H NMR光谱中显示出两组信号。将信号分配给反式（72％）和顺式（28％）构象体。4的晶体学分析表明仅顺式构象以结晶状态存在。在苄基（2S）-1-[（2R / S）-3-甲氧基-2-甲基-2-
• 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.