N-(2-((Trimethylsilyl)ethoxy)carbonyl)pyrrole | 126554-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(2-((Trimethylsilyl)ethoxy)carbonyl)pyrrole
• 英文别名: 2-trimethylsilylethyl pyrrole-1-carboxylate
• CAS: 126554-32-3
• 化学式: C₁₀H₁₇NO₂Si
• 分子量: 211.336
• InChiKey: HFXXWTGLMAXOCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(2-((Trimethylsilyl)ethoxy)carbonyl)pyrrole 在 RhCl(PPh₃)3 rhodium(II) hexanoate 、 氢气 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 24.0h， 生成 Methyl 8-((2-(trimethylsilyl)ethoxy)carbonyl)-8-azabicyclo<3.2.1>oct-2-ene-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
• 作为产物：
  描述：

  吡咯-1-羧酸氯化物 、 2-(三甲硅基)乙醇 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到N-(2-((Trimethylsilyl)ethoxy)carbonyl)pyrrole
  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。
• Synthesis of <i>N</i>-alkoxycarbonyl Pyrroles from <i>O</i>-Substituted Carbamates: A Synthetically Enabling Pyrrole Protection Strategy
  作者：Jodie L. Hann、Catherine L. Lyall、Gabriele Kociok-Köhn、Simon E. Lewis

  DOI：10.1021/acs.joc.3c01257

  日期：2023.10.6

  5-dimethoxytetrahydrofuran gives N-alkoxycarbonyl pyrroles in a single step and in good yield. By this method, several common amine protecting groups can be introduced on the pyrrole nitrogen. With the exception of N-Boc, N-alkoxycarbonyl groups have seen only minimal use for protection of the pyrrole nitrogen to date. Here, we show that N-alkoxycarbonyl protection can endow pyrrole with distinct reactivity in comparison

  容易获得的O-取代氨基甲酸酯与2,5-二甲氧基四氢呋喃的缩合一步即可得到N-烷氧基羰基吡咯，收率良好。通过该方法，可以在吡咯氮上引入几种常见的胺保护基。迄今为止，除了N -Boc 之外，N-烷氧基羰基仅很少用于保护吡咯氮。在这里，我们表明，与N-磺酰基保护相比， N-烷氧基羰基保护可以赋予吡咯不同的反应性，例如，在使用羧酸和磺酸酐活化剂的吡咯酰化方案中。
• 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：——
• 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.