pyrrolo<2,1-a>isoindol-5-one-1-carboxy-2-one-3-methyl methyl ester | 96952-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: pyrrolo<2,1-a>isoindol-5-one-1-carboxy-2-one-3-methyl methyl ester
• 英文别名: 2,5-Dioxo-3-methyl-2,3-dihydro-5H-pyrrolo<2,1-a>isoindol-1-carbonsaeuremethylester；methyl 3-methyl-2,5-dioxo-3H-pyrrolo[2,1-a]isoindole-1-carboxylate
• CAS: 96952-69-1
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: GKDUMRHFRJGAFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pyrrolo<2,1-a>isoindol-5-one-1-carboxy-2-one-3-methyl methyl ester 、 5-溴戊酸乙酯 以43%的产率得到
  参考文献：
  名称：

  Nudelman Abraham, Marcoviet Dana, Nachum Ayelet, Heterocycles, 38 (1994) N 4, S 751-758

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl 3-oxo-4-phthalimidopentanoate 以57%的产率得到
  参考文献：
  名称：

  Nudelman Abraham, Marcoviet Dana, Nachum Ayelet, Heterocycles, 38 (1994) N 4, S 751-758

  摘要：

  DOI：

文献信息

• Pyrrole[2,1-a]isoindole-5-ones and Benz[3,4]azocin-1(2H)-1,4,6-triones
  作者：Abraham Nudelman、Dana Marcovici、Ayelet Nachum

  DOI：10.3987/com-93-6567

  日期：——

  Pyrrolo[2,1-a]isoindol-5-ones (8) have been obtained by base catalyzed cyclization and O-alkylation of N-phthalimido-substituted beta-keto ester (1) via intermediate (7). Reaction of 1 with MeI/acetone/K2CO3 gave the C-alkylation product (3). With bulkier reagents than MeI in a variety of solvents and in the presence of various bases, compounds (8) were isolated. In the absence of an alkylating agent, reaction of 1 with NaH/DMF gave pyrrolo[2,1-a]isoindol-5-one derivative (6), found at room temperature in its keto form (6a) and at higher temperatures in the enol form pyrrolo[2,1-a]isoindol-5-one-1-carboxy-2-hydroxy-3-methyl methyl ester (6b), and 11 which at room temperature already appeared in the enol form. Reaction of acyl chloride (14) with ethyl cyanoacetate/NaH did not stop at ethyl-2-cyano-4-N-isoindol-3-oxopentanoate (15) but proceeded to rearrange to a single diastereomeric benz[3,4]azocin-1(2H)-1,4,6-trione (17).