(S)-(+)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid | 165114-49-8

• 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-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
• 英文别名: (2S)-2-methyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid；(S)-(+)-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid；(S)-(+)-3,4Dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid；(S)-2-Methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid；(2S)-2-methyl-3-oxo-4H-1,4-benzoxazine-2-carboxylic acid
• CAS: 165114-49-8
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: HNDTULADLKGMDH-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R)-N-(2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carbonyl)-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  Kikelj, Danijel; Povsic, Lucka; Stalc, Anton, Medicinal Chemistry Research, 1996, vol. 6, # 2, p. 118 - 127

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-monomethyl 2-methyl-2-(2-nitrophenoxy)malonate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 反应 24.0h， 生成 (S)-(+)-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

• NOVEL HETEROCYCLIC ACYLDIPEPTIDES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：UNIVERZA V LJUBLJANI, FAKULTETA ZA NARAVOSLOVJE IN TEHNOLOGIJO, ODDELEK ZA FARMACIJO

  公开号：EP0695308B1

  公开（公告）日：1998-07-01
• US5824652A
  申请人：——

  公开号：US5824652A

  公开（公告）日：1998-10-20
• Kikelj, Danijel; Povsic, Lucka; Stalc, Anton, Medicinal Chemistry Research, 1996, vol. 6, # 2, p. 118 - 127
  作者：Kikelj, Danijel、Povsic, Lucka、Stalc, Anton、Pristovsek, Primoz、Kidric, Jurkica

  DOI：——

  日期：——
• 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.