(αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-propionic acid | 253353-11-6

• 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: (αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-propionic acid
• 英文别名: (2S)-3-(3,4-dioxo-2-propan-2-yloxycyclobuten-1-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 253353-11-6
• 化学式: C₁₈H₁₉NO₇
• 分子量: 361.351
• InChiKey: QGIPKQZMQXSJPV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (αS)-3,4-dioxo-2-(1-methylethoxy)-α-phenylmethyloxycarbonylamino-1-cyclobutene-1-propionic acid 在 盐酸 作用下， 反应 3.0h， 以87%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
• 作为产物：
  描述：

  1,1-dimethylethyl (αS)-β-(1,1-dimethylethoxycarbonyl)-3,4-dioxo-2-(1-methylethoxy)-α-(phenylmethyloxycarbonylamino)-1-cyclobutene-1-propionate 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 以80%的产率得到(αS)-3,4-dioxo-2-(1-methylethoxy)-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.