(S)-α-amino-3,4-dioxo-2-hydroxy-1-cyclobutene-1-butyric acid | 253353-18-3

• 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-butyric acid
• 英文别名: (2S)-2-amino-4-(2-hydroxy-3,4-dioxocyclobuten-1-yl)butanoic acid
• CAS: 253353-18-3
• 化学式: C₈H₉NO₅
• 分子量: 199.163
• InChiKey: PXQGSZRPKPFMJK-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-butyric acid 、 甲氧基-三氟甲基苯 在 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 12.0h， 以98%的产率得到(αS,2'R)-3,4-dioxo-2-hydroxy-α-(2-methoxy-1-oxo-3,3,3-trifluoro-2-phenylpropylamino)-1-cyclobutene-1-butyric 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
• 作为产物：
  描述：

  (αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-butyric acid 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以98%的产率得到(S)-α-amino-3,4-dioxo-2-hydroxy-1-cyclobutene-1-butyric 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
• Efficient Synthesis of a Novel 4-Hydroxy-2,3-dioxocyclobut-1-enyl Group Containing Amino Acids
  作者：Tetsuro Shinada、Ken-ichi Hayashi、Toshihiro Hayashi、Yasutaka Yoshida、Manabu Horikawa、Keiko Shimamoto、Yasushi Shigeri、Noboru Yumoto、Yasufumi Ohfune

  DOI：10.1021/ol990286g

  日期：1999.11.1

  [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.