1,1-dimethylethyl (αS)-β-(1,1-dimethylethoxycarbonyl)-3,4-dioxo-2-(1-methylethoxy)-α-(phenylmethyloxycarbonylamino)-1-cyclobutene-1-propionate | 253353-10-5

• 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: 1,1-dimethylethyl (αS)-β-(1,1-dimethylethoxycarbonyl)-3,4-dioxo-2-(1-methylethoxy)-α-(phenylmethyloxycarbonylamino)-1-cyclobutene-1-propionate
• CAS: 253353-10-5
• 化学式: C₂₇H₃₅NO₉
• 分子量: 517.576
• InChiKey: ULSAXYKLKFXIBD-NNBQYGFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  134.3
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (αS)-β-(1,1-dimethylethoxycarbonyl)-3,4-dioxo-2-(1-methylethoxy)-α-(phenylmethyloxycarbonylamino)-1-cyclobutene-1-propionate 在 盐酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.17h， 生成 (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
• 作为产物：
  描述：

  1,1-dimethylethyl (αS)-2,3-bis(1-methylethoxy)-β-(1,1-dimethylethoxycarbonyl)-1-hydroxy-4-oxo-α-phenylmethyloxycarbonylamino-2-cyclobutene-1-propionate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以63%的产率得到1,1-dimethylethyl (αS)-β-(1,1-dimethylethoxycarbonyl)-3,4-dioxo-2-(1-methylethoxy)-α-(phenylmethyloxycarbonylamino)-1-cyclobutene-1-propionate
  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