Methyl N-(methoxycarbonyl)-8-azabicyclo<3.2.1>octa-2,6-diene-2-carboxylate | 126554-31-2

• 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: Methyl N-(methoxycarbonyl)-8-azabicyclo<3.2.1>octa-2,6-diene-2-carboxylate
• 英文别名: methyl 8-Methoxycarbonyl-8-azabicyclo[3.2.1]octa-2,6-diene-2-carboxylate；Dimethyl 8-azabicyclo[3.2.1]octa-2,6-diene-2,8-dicarboxylate
• CAS: 126554-31-2
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: TXWKITSZJDHSOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  325.2±42.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-丁烯酸甲酯 在 六甲基磷酰三胺 、 对甲苯磺酰叠氮 、 rhodium(II) hexanoate 、 lithium diisopropyl amide 作用下， 以 正己烷 为溶剂， 反应 24.5h， 生成 Methyl N-(methoxycarbonyl)-8-azabicyclo<3.2.1>octa-2,6-diene-2-carboxylate
  参考文献：
  名称：

  Synthesis of (.+-.)-ferruginine and (.+-.)-anhydroecgonine methyl-ester by a tandem cyclopropanation/Cope rearrangement

  摘要：

  Rhodium(II) acetate catalyzed decomposition of vinyldiazomethanes in the presence of N-(alkoxycarbonyl)pyrroles led to the synthesis of 8-azabicyclo[3.2.1]octa-2,6-dienes. The vinylcarbenoids generated from vinyldiazomethanes with a single electron-withdrawing group exhibited competing reactivity at the vinyl terminus in addition to the carbenoid site. Good regiocontrol was possible, however, by appropriate choice of catalyst and solvent. The practicality of this new approach to tropane alkaloids was demonstrated through short syntheses of (+/-)-ferruginine, (+/-)-anhydroecgonine methyl ester, and the lower homologue of (+/-)-anatoxin a.

  DOI：

  10.1021/jo00019a044

文献信息

• Novel entry to the tropane system by reaction of rhodium(II) acetate stabilized vinylcarbenoids with pyrroles
  作者：Huw M.L. Davies、Wendy B. Young、H.David Smith

  DOI：10.1016/s0040-4039(01)80766-8

  日期：1989.1

  Rhodium(II) acetate catalyzed decomposition of vinyldiazomethanes in the presence of N-alkoxycarbonylpyrroles provides a direct entry to the skeleton of tropane alkaloids. Similar reactions with N-alkylpyrroles result in the formation of alkylation products.

  在N-烷氧基羰基吡咯的存在下，乙酸铑（II）催化的乙烯基重氮甲烷的分解提供了直接进入托烷生物碱骨架的入口。与N-烷基吡咯的类似反应导致烷基化产物的形成。
• DAVIES, HUW M. L.;YOUNG, WENDY B.;SMITH, H. DAVID, TETRAHEDRON LETT., 30,(1989) N5, C. 4653-4656
  作者：DAVIES, HUW M. L.、YOUNG, WENDY B.、SMITH, H. DAVID

  DOI：——

  日期：——
• US5591854A
  申请人：——

  公开号：US5591854A

  公开（公告）日：1997-01-07
• [EN] ENANTIOSELECTIVE SYNTHESIS OF SEVEN-MEMBERED CARBOCYCLES AND TROPANES<br/>[FR] SYNTHESE SELECTIVE D'ENANTIOMERES DE CYCLES CARBONES A SEPT ELEMENTS ET DE TROPANES
  申请人：WAKE FOREST UNIVERSITY

  公开号：WO1996011928A1

  公开（公告）日：1996-04-25

  (EN) A process of enantioselective synthesis of seven-membered carbocycles in the presence of di-rhodium(II) tetracarboxylate catalysts.(FR) L'invention concerne un précédé de synthèse sélective d'énantiomères de cycles carbonés à sept éléments, en présence des catalyseurs du type di-rhodium (II) tétracarboxylate.
• Synthesis of (.+-.)-ferruginine and (.+-.)-anhydroecgonine methyl-ester by a tandem cyclopropanation/Cope rearrangement
  作者：Huw M. L. Davies、Elie Saikali、Wendy B. Young

  DOI：10.1021/jo00019a044

  日期：1991.9

  Rhodium(II) acetate catalyzed decomposition of vinyldiazomethanes in the presence of N-(alkoxycarbonyl)pyrroles led to the synthesis of 8-azabicyclo[3.2.1]octa-2,6-dienes. The vinylcarbenoids generated from vinyldiazomethanes with a single electron-withdrawing group exhibited competing reactivity at the vinyl terminus in addition to the carbenoid site. Good regiocontrol was possible, however, by appropriate choice of catalyst and solvent. The practicality of this new approach to tropane alkaloids was demonstrated through short syntheses of (+/-)-ferruginine, (+/-)-anhydroecgonine methyl ester, and the lower homologue of (+/-)-anatoxin a.