methyl 4-N-isoindol-3-oxopentanoate | 149849-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 4-N-isoindol-3-oxopentanoate
• 英文别名: methyl (4S)-4-(1,3-dioxoisoindol-2-yl)-3-oxopentanoate
• CAS: 149849-86-5
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: JMEHOMDMWLODLE-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-溴戊酸乙酯 、 methyl 4-N-isoindol-3-oxopentanoate 在 sodium hydride 、 sodium iodide 作用下， 生成 pyrrolo<2,1-a>isoindol-5-one-1-carboxy-2--3-methyl methyl ester
  参考文献：
  名称：

  Pyrrole[2,1-a]isoindole-5-ones and Benz[3,4]azocin-1(2H)-1,4,6-triones

  摘要：

  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).

  DOI：

  10.3987/com-93-6567
• 作为产物：
  描述：

  monomethyl monopotassium malonate 、 邻苯二甲酰基-L-丙氨酸 在 N,N'-羰基二咪唑 、 magnesium chloride 作用下， 生成 methyl 4-N-isoindol-3-oxopentanoate
  参考文献：
  名称：

  Pyrrole[2,1-a]isoindole-5-ones and Benz[3,4]azocin-1(2H)-1,4,6-triones

  摘要：

  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).

  DOI：

  10.3987/com-93-6567

文献信息

• Diastereoselective Synthesis of &amp;#947;-Phthalimido-&amp;#946;-Hydroxy Esters and N-Protected 4-Amino-1,3-Diols Starting from Natural &amp;#945;-Amino Acids
  作者：Amel Essersi、Ridha Touati、Bechir Hassine

  DOI：10.2174/157017810790533869

  日期：2010.1.1

  An efficient diastereoselective synthesis of gamma-phthalimido-beta-hydroxy esters and N-protected 4-amino-1,3-diols, starting from natural amino acids is described. The key synthetic strategies involve diastereoselective reduction of gamma-phthalimido-beta-keto esters with NaBH4 as hydride reducing. The diastereoselective reduction has been found to be highly selective if carried out in methanol at -78 degrees C. Furthermore, the resulting diastereomeric mixture of the reduced products was successfully and cleanly separated by column chromatography.
• 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).