2-diazo-3-(2-oxopyrrolidin-1-yl)-3-oxopropionic acid ethyl ester | 196881-96-6

• 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: 2-diazo-3-(2-oxopyrrolidin-1-yl)-3-oxopropionic acid ethyl ester
• 英文别名: Ethyl 2-diazo-3-oxo-3-(2-oxopyrrolidin-1-yl)propanoate；ethyl 2-diazo-3-oxo-3-(2-oxopyrrolidin-1-yl)propanoate
• CAS: 196881-96-6
• 化学式: C₉H₁₁N₃O₄
• 分子量: 225.204
• InChiKey: QXUGQXCIIGOZET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-diazo-3-(2-oxopyrrolidin-1-yl)-3-oxopropionic acid ethyl ester 在 dirhodium tetraacetate 水 作用下， 以 苯 为溶剂， 生成 2-Hydroxy-3-oxo-3-(2-oxo-pyrrolidin-1-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  Rh2(OAc)4-catalyzed reactions of α-diazoimides: a simple and novel synthesis of mono- and bis(2,3-fused perhydrooxazol-4-one) systemsElectronic supplementary information (ESI) available: experimental procedure and spectral data for compounds 2a–p, 3, 5a–f. See http://www.rsc.org/suppdata/cc/b2/b211717g/

  摘要：

  简单地说，通过外部氧亲核试剂捕获中间体异构化锰内锚1,3-二偶极子，导致形成了新的杂环体系。使用二元醇作为反应物，在一项操作中形成了四个碳氧键，最终得到了双(2,3-融合的芐氧乙酰肼-4-酮)体系。

  DOI：

  10.1039/b211717g
• 作为产物：
  描述：

  2-吡咯烷酮 、 chlorocarbonyl-diazo-acetic acid ethyl ester 在 lithium hexamethyldisilazane 作用下， 生成 2-diazo-3-(2-oxopyrrolidin-1-yl)-3-oxopropionic acid ethyl 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

• PPh3-mediated reactions of diazoimides in water: a facile synthesis of fused triazine derivatives
  作者：Sengodagounder Muthusamy、Pandurangan Srinivasan

  DOI：10.1016/j.tetlet.2009.01.021

  日期：2009.3

  Triphenylphosphine-mediated reactions of diazoimides in water were carried out under mild conditions to afford several triazine derivatives in high yields. We have demonstrated an environment friendly methodology to synthesize triazine derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• Rh2(OAc)4-catalyzed reactions of α-diazoimides: a simple and novel synthesis of mono- and bis(2,3-fused perhydrooxazol-4-one) systemsElectronic supplementary information (ESI) available: experimental procedure and spectral data for compounds 2a–p, 3, 5a–f. See http://www.rsc.org/suppdata/cc/b2/b211717g/
  作者：Sengodagounder Muthusamy、Chidambaram Gunanathan

  DOI：10.1039/b211717g

  日期：2003.1.23

  Simply, trapping the intermediate isomünchnone 1,3-dipoles by the external oxygen nucleophiles resulted in new heterocyclic systems and the use of diols led to the formation of four carbon-oxygen bonds in a single operation which eventually delivered bis(2,3-fused perhydrooxazol-4-one) systems.

  简单地说，通过外部氧亲核试剂捕获中间体异构化锰内锚1,3-二偶极子，导致形成了新的杂环体系。使用二元醇作为反应物，在一项操作中形成了四个碳氧键，最终得到了双(2,3-融合的芐氧乙酰肼-4-酮)体系。
• 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.