6-Hydroxy-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | 1255098-54-4

• 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: 6-Hydroxy-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• 英文别名: Methyl N-Boc-6-hydroxy-indoline-2-carboxylate；1-O-tert-butyl 2-O-methyl 6-hydroxy-2,3-dihydroindole-1,2-dicarboxylate
• CAS: 1255098-54-4
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: MGEQMUYQRDRBHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 caesium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 22.5h， 生成 6-Carboxymethoxy-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester
  参考文献：
  名称：

  The Design and Enzyme-Bound Crystal Structure of Indoline Based Peptidomimetic Inhibitors of Hepatitis C Virus NS3 Protease

  摘要：

  The design of a series of peptidomimetic inhibitors of the hepatitis C virus NS3 protease is described. These inhibitors feature an indoline-2-carboxamide as a novel heterocyclic replacement for the P3 amino acid residue and N-terminal capping group of tripeptide based inhibitors. The crystal structure of the ternary NS3/NS4A/inhibitor complex for the most active molecule in this series highlights its suitability as an N-terminal capping group of a dipeptide inhibitor of the NS3 protease.

  DOI：

  10.1021/jm049435d
• 作为产物：
  描述：

  1H-Indole-1,2-dicarboxylic acid, 6-(phenylmethoxy)-,1-(1,1-dimethylethyl) 2-methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以96%的产率得到6-Hydroxy-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  The Design and Enzyme-Bound Crystal Structure of Indoline Based Peptidomimetic Inhibitors of Hepatitis C Virus NS3 Protease

  摘要：

  The design of a series of peptidomimetic inhibitors of the hepatitis C virus NS3 protease is described. These inhibitors feature an indoline-2-carboxamide as a novel heterocyclic replacement for the P3 amino acid residue and N-terminal capping group of tripeptide based inhibitors. The crystal structure of the ternary NS3/NS4A/inhibitor complex for the most active molecule in this series highlights its suitability as an N-terminal capping group of a dipeptide inhibitor of the NS3 protease.

  DOI：

  10.1021/jm049435d