(S)-3,4-dioxo-2-hydroxy-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-propionic acid | 253353-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3,4-dioxo-2-hydroxy-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-propionic acid
• 英文别名: (2S)-3-(2-hydroxy-3,4-dioxocyclobuten-1-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 253353-26-3
• 化学式: C₁₅H₁₃NO₇
• 分子量: 319.271
• InChiKey: XPFAJMRIAKZSDB-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3,4-dioxo-2-hydroxy-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-propionic acid 、 L-缬氨酸甲酯盐酸盐 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以7%的产率得到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 、 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 24.0h， 生成 (S)-3,4-dioxo-2-hydroxy-α-phenylmethyloxycarbonylamino-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

• 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.