1-(2-Methoxycarbonyl-acetyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester | 196882-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(2-Methoxycarbonyl-acetyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester
• 英文别名: Methyl 1-(3-methoxy-3-oxopropanoyl)-5-oxopyrrolidine-3-carboxylate
• CAS: 196882-11-8
• 化学式: C₁₀H₁₃NO₆
• 分子量: 243.216
• InChiKey: HPWMHVRHHNJQJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-Methoxycarbonyl-acetyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester 在 对甲苯磺酰叠氮 、 Rh₂(pfm)4 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 tetrahydro-1,3,5-trioxo-2-methyl-7H-4,9a-epoxy-1H-pyrrolo[3,4-g]indolizine-4,8-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  π-Facial Diastereoselection in [3 + 2]-Cycloadditions of Isomünchnone Dipoles

  摘要：

  The Rh(II)-catalyzed reaction of 1-[diazo(methoxycarbonyl)acetyl]-2-oxopyrrolidine derivatives led to the formation of ring-fused isomunchnone betaines which are trapped with various dipolarophiles to give the corresponding [3 + 2]-cycloadducts in excellent yield. The cycloaddition reaction proceeded with high levels of diastereoselectivity leading to the predominant formation of the exo dipolar cycloadduct. The influence of substituents on the stereoselectivity of the reaction was investigated. Diastereotopic facial selectivity by the dipolarophile on the mesoionic betaine was found to depend upon the nature of the stereogenic center. Inclusion of substituents at any position of the fused five-membered ring was found to enhance exo selectivity. Isomunchnone dipoles derived from pyrrolidinones containing a carboalkoxy substituent in the 5-position of the ring afforded mainly exo-syn cycloadducts. In contrast, when a methyl group was present at the 3-position of the pyrrolidinone ring, the facial selectivity was reversed with the exo-anti adduct being the major product. A computational study was carried out to rationalize the observed product distribution.

  DOI：

  10.1021/jo970625o
• 作为产物：
  描述：

  丙二酸甲酯酰氯 、 5-吡咯烷酮-3-甲酸甲酯 以 苯 为溶剂， 反应 3.0h， 以70%的产率得到1-(2-Methoxycarbonyl-acetyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  π-Facial Diastereoselection in [3 + 2]-Cycloadditions of Isomünchnone Dipoles

  摘要：

  The Rh(II)-catalyzed reaction of 1-[diazo(methoxycarbonyl)acetyl]-2-oxopyrrolidine derivatives led to the formation of ring-fused isomunchnone betaines which are trapped with various dipolarophiles to give the corresponding [3 + 2]-cycloadducts in excellent yield. The cycloaddition reaction proceeded with high levels of diastereoselectivity leading to the predominant formation of the exo dipolar cycloadduct. The influence of substituents on the stereoselectivity of the reaction was investigated. Diastereotopic facial selectivity by the dipolarophile on the mesoionic betaine was found to depend upon the nature of the stereogenic center. Inclusion of substituents at any position of the fused five-membered ring was found to enhance exo selectivity. Isomunchnone dipoles derived from pyrrolidinones containing a carboalkoxy substituent in the 5-position of the ring afforded mainly exo-syn cycloadducts. In contrast, when a methyl group was present at the 3-position of the pyrrolidinone ring, the facial selectivity was reversed with the exo-anti adduct being the major product. A computational study was carried out to rationalize the observed product distribution.

  DOI：

  10.1021/jo970625o

文献信息

• π-Facial Diastereoselection in [3 + 2]-Cycloadditions of Isomünchnone Dipoles
  作者：Albert Padwa、Michael Prein

  DOI：10.1021/jo970625o

  日期：1997.10.1

  The Rh(II)-catalyzed reaction of 1-[diazo(methoxycarbonyl)acetyl]-2-oxopyrrolidine derivatives led to the formation of ring-fused isomunchnone betaines which are trapped with various dipolarophiles to give the corresponding [3 + 2]-cycloadducts in excellent yield. The cycloaddition reaction proceeded with high levels of diastereoselectivity leading to the predominant formation of the exo dipolar cycloadduct. The influence of substituents on the stereoselectivity of the reaction was investigated. Diastereotopic facial selectivity by the dipolarophile on the mesoionic betaine was found to depend upon the nature of the stereogenic center. Inclusion of substituents at any position of the fused five-membered ring was found to enhance exo selectivity. Isomunchnone dipoles derived from pyrrolidinones containing a carboalkoxy substituent in the 5-position of the ring afforded mainly exo-syn cycloadducts. In contrast, when a methyl group was present at the 3-position of the pyrrolidinone ring, the facial selectivity was reversed with the exo-anti adduct being the major product. A computational study was carried out to rationalize the observed product distribution.