(S)-α-amino-3,4-dioxo-2-hydroxy-1-cyclobutene-1-propionic acid | 253353-12-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-α-amino-3,4-dioxo-2-hydroxy-1-cyclobutene-1-propionic acid
• 英文别名: (2S)-2-amino-3-(2-hydroxy-3,4-dioxocyclobuten-1-yl)propanoic acid
• CAS: 253353-12-7
• 化学式: C₇H₇NO₅
• 分子量: 185.136
• InChiKey: RTGLOAJDIKEHRK-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-α-amino-3,4-dioxo-2-hydroxy-1-cyclobutene-1-propionic acid 在 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl (2S)-2-[[2-[(2S)-3-[[(2S)-1-methoxy-3-methyl-1-oxobutan-2-yl]amino]-3-oxo-2-(phenylmethoxycarbonylamino)propyl]-3,4-dioxocyclobuten-1-yl]amino]-3-methylbutanoate
  参考文献：
  名称：

  Efficient Synthesis of a Novel 4-Hydroxy-2,3-dioxocyclobut-1-enyl Group Containing Amino Acids

  摘要：

  [GRAPHICS]Syntheses of novel amino acids possessing a squaryl group, 1-3, in an optically active form are described. The syntheses of 1-3 were conducted by a concise route involving (1) an aldol addition of an enolate derived from Gly, L-Asp, or L-Glu to diisopropyl squarate (4) and (2) an efficient decarboxylation of the aldol adducts based on the electron-withdrawing property of the squaryl group. Introducing N-protected group to 2 and 3 and peptide formation reactions are also described.

  DOI：

  10.1021/ol990286g
• 作为产物：
  描述：

  (3S)-2-(2-hydroxy-3,4-dioxocyclobuten-1-yl)-3-(phenylmethoxycarbonylamino)butanedioic acid 在 盐酸 作用下， 反应 12.0h， 以240 mg的产率得到(S)-α-amino-3,4-dioxo-2-hydroxy-1-cyclobutene-1-propionic acid
  参考文献：
  名称：

  Efficient Synthesis of a Novel 4-Hydroxy-2,3-dioxocyclobut-1-enyl Group Containing Amino Acids

  摘要：

  [GRAPHICS]Syntheses of novel amino acids possessing a squaryl group, 1-3, in an optically active form are described. The syntheses of 1-3 were conducted by a concise route involving (1) an aldol addition of an enolate derived from Gly, L-Asp, or L-Glu to diisopropyl squarate (4) and (2) an efficient decarboxylation of the aldol adducts based on the electron-withdrawing property of the squaryl group. Introducing N-protected group to 2 and 3 and peptide formation reactions are also described.

  DOI：

  10.1021/ol990286g

文献信息

• JP2001122838A
  申请人：——

  公开号：JP2001122838A

  公开（公告）日：2001-05-08