1,1-dimethylethyl α-(1,1-dimethylethoxy)carbonylamino-3,4-dioxo-2-(1-methylethoxy)-1-cyclobutene-1-acetate | 253353-08-1

• 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: 1,1-dimethylethyl α-(1,1-dimethylethoxy)carbonylamino-3,4-dioxo-2-(1-methylethoxy)-1-cyclobutene-1-acetate
• 英文别名: tert-butyl (tert-butoxycarbonyl)(2-isopropoxy-3,4-dioxocyclobut-1-enyl)methylcarbamate；Tert-butyl 2-(3,4-dioxo-2-propan-2-yloxycyclobuten-1-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 253353-08-1
• 化学式: C₁₈H₂₇NO₇
• 分子量: 369.415
• InChiKey: XUVNWBRJYZABGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl α-(1,1-dimethylethoxy)carbonylamino-3,4-dioxo-2-(1-methylethoxy)-1-cyclobutene-1-acetate 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以72%的产率得到3-(aminomethyl)-4-hydroxycyclobutene-1,2-dione
  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 2,3-bis(1-methylethoxy)-α-(1,1-dimethylethoxy)carbonylamino-1-hydroxy-4-oxo-2-cyclobutene-1-acetate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到1,1-dimethylethyl α-(1,1-dimethylethoxy)carbonylamino-3,4-dioxo-2-(1-methylethoxy)-1-cyclobutene-1-acetate
  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

• Syntheses of α-Amino Squaric Acids Using an Aminomalonate Equivalent Bearing a Squaryl Group
  作者：Tetsuro Shinada、Yasufumi Ohfune、Toshikazu Ishida

  DOI：10.1055/s-2005-872109

  日期：——

  The synthesis of an amino acid analogue bearing a squaryl group as a carboxylic acid surrogate (sq-AA; 2) has been developed. Aminomalonate equivalent 6 was used as a nucleophilic synthon whose alkylation or conjugate addition reaction followed by deprotection and decarboxylation reaction gave sq-AAs.

  已经开发了带有方酸基团的氨基酸类似物作为羧酸替代物 (sq-AA; 2) 的合成。氨基丙二酸等价物 6 用作亲核合成子，其烷基化或共轭加成反应，然后进行脱保护和脱羧反应，得到 sq-AAs。
• 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.