7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid trimethyl ester | 19169-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid trimethyl ester
• 英文别名: N-Methoxycarbonyl-7-aza-bicyclo<2.2.1>heptadien-(2,5)-dicarbonsaeure-(2,3)-dimethylester, 2,3,7-Trimethoxycarbonyl-7-aza-norbornadien-(2,5)；N-Methoxycarbonyl-7-aza-bicyclo<2.2.1>heptadien-(2,5)-dicarbonsaeure-(2,3)-dimethylester；2,3,7-Trimethyl 7-azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylate；trimethyl 7-azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylate
• CAS: 19169-19-8
• 化学式: C₁₂H₁₃NO₆
• 分子量: 267.238
• InChiKey: JDLKHLJNEAETQF-UHFFFAOYSA-N

物化性质

• 沸点：
  367.7±42.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  环辛炔 、 7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid trimethyl ester 以 二氯甲烷 为溶剂， 100.0 ℃ 、600.0 MPa 条件下， 反应 96.0h， 以22%的产率得到
  参考文献：
  名称：

  Cycloaddition Reactions of Oxaquadricyclane, Oxanorbornadiene, and Related Compounds with Cyclooctyne

  摘要：

  Dimethyl oxaquadricyclane-2,3-dicarboxylate (1) with cyclooctyne (CO) gave, via carbonyl ylide (3a), a mixture of the exo and endo 1:1 adducts (2a, 2b) along with the novel 1:2 adduct (2c), whereas the carbocyclic analogs underwent [sigma 2s + sigma 2s + pi 2s]cycloaddition. The first examples of inverse electron demand homo-Diels-Alder reactions of oxa-, aza- and carbo-norbornadienes with CO were also described.

  DOI：

  10.3987/com-98-s36
• 作为产物：
  描述：

  甲基吡咯-1-羧酸酯 、 丁炔二酸二甲酯 生成 7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid trimethyl ester
  参考文献：
  名称：

  NOLAND W. E.; LEE CHANG KIU, J. ORG. CHEM., 1980, 45, NO 23, 4573-4582

  摘要：

  DOI：

文献信息

• Identification of the tricarbonyliron complex of 7-azabicyclo[2.2.1]heptadiene derivatives as the intermediate in nitrene extrusion reactions
  作者：Chia-Hsing Sun、Tahsin J. Chow

  DOI：10.1039/c39880000535

  日期：——

  Several tricarbonyliron complexes of N-substituted 7-aza-2,3-bismethoxycarbonylbicyclo[2.2.1]heptadiene have been isolated and identified as the intermediates of nitrene-extrusion reactions.

  N-取代的7-氮杂-2，3-双甲氧基羰基双环[2.2.1]庚二烯的几种三羰基铁配合物已被分离出来，并被确定为腈挤压反应的中间体。
• Regioselective synthesis of η3-(N-methoxycarbonyl-7-azabicyclo[2.2.1]he ta-2,5-dienyl)-η5-(C5Me5)RuCl complexes
  作者：Zhengming Chen、Lubin Luo、Steven P. Nolan、Jeffrey L. Petersen、Mark L. Trudell

  DOI：10.1016/s0022-328x(96)06827-1

  日期：1997.4

  The reactions of Cp*Ru(COD)Cl and CpRu(COD)Cl with N-methoxycarbonyl-7-azabicyclo[2.2.1]hepta-2,5-diene derivatives were found to give eta(3)-[N(CO2Me)C6H3(2-p-MeC6H4SO2)(6-CO2Me)(5-Me)]CpRuCl and eta(3)-[N(CO2Me)-7-azabicyclo[2.2.1]heptadienyl]Cp*RuCl complexes in good yields (54-78%). The coordination reaction was found to take place regioselectively at the least substituted pi-bond of the N-methoxycarbonyl-7-azabicyclo[2.2.1]hepta-2,5-diene derivatives. The structures of the complexes were determined by H-1 and C-13 NMR and the structure of eta(3)-[N(CO2Me)C6H3(2-p-MeC6H4SO2)(6-CO2Me)(5-Me)]Cp*RuCl was unequivocally established by X-ray crystallography.