1-(5,6,7,8-tetrahydro-1-indolizinyl)-1-ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5,6,7,8-tetrahydro-1-indolizinyl)-1-ethanone
• 英文别名: 1-(5,6,7,8-tetrahydroindolizin-1-yl)ethan-1-one；1-acetyl-5,6,7,8-tetrahydroindolizine；1-(5,6,7,8-Tetrahydroindolizin-1-yl)ethanone
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: LMJOAKRDNPWSSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氰甲基磷酸二乙酯 、 1-(5,6,7,8-tetrahydro-1-indolizinyl)-1-ethanone 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 15.0h， 以60%的产率得到
  参考文献：
  名称：

  2-取代的 3-氰基吡咯的途径：丹那代尔和 Suffrutine A 的合成

  摘要：

  标题化合物是由 4,4-二甲氧基丁腈和各自的酯通过克莱森缩合和随后的 Paal-Knorr 吡咯合成以两步顺序制备的。该序列可以作为一锅程序进行，在两个步骤中以 47-72% 的产率提供吡咯（13 个例子）。该方法的分子内变体被应用于从各自的三苯甲基保护的ω-氨基链烷酸酯全合成丹那达和suffrutine A。

  DOI：

  10.1021/acs.joc.6b01298
• 作为产物：
  描述：

  3-乙酰基吡咯 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 1-(5,6,7,8-tetrahydro-1-indolizinyl)-1-ethanone
  参考文献：
  名称：

  Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH

  摘要：

  Oxidative radical cyclisation using Bu3SnH has been used for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles from imidazolecarbaldehydes and acylpyrroles respectively. The intermediate nucleophilic N-alkyl radicals cyclise onto imidazole and pyrrole rings followed by oxidative re-aromatisation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10052-1

文献信息

• Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH
  作者：Fawaz Aldabbagh、W.Russell Bowman、Emma Mann

  DOI：10.1016/s0040-4039(97)10052-1

  日期：1997.11

  Oxidative radical cyclisation using Bu3SnH has been used for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles from imidazolecarbaldehydes and acylpyrroles respectively. The intermediate nucleophilic N-alkyl radicals cyclise onto imidazole and pyrrole rings followed by oxidative re-aromatisation. (C) 1997 Elsevier Science Ltd.
• Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles
  作者：Fawaz Aldabbagh、W.Russell Bowman、Emma Mann、Alexandra M.Z. Slawin

  DOI：10.1016/s0040-4020(99)00419-6

  日期：1999.6

  A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N-(omega-bromoalkyl) or N-[omega-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regioselective radical cyclisation onto the azole rings followed by oxidative re-aromatisation, (C) 1999 Elsevier Science Ltd. Ail rights reserved.
• A Route to 2-Substituted 3-Cyanopyrroles: Synthesis of Danaidal and Suffrutine A
  作者：Johannes M. Wahl、Thorsten Bach

  DOI：10.1021/acs.joc.6b01298

  日期：2016.7.15

  two-step sequence from 4,4-dimethoxybutyronitrile and the respective esters by Claisen condensation and subsequent Paal–Knorr pyrrole synthesis. The sequence could be performed as a one-pot procedure delivering the pyrroles in yields of 47–72% over two steps (13 examples). Intramolecular variants of the method were applied to the total synthesis of danaidal and suffrutine A from the respective trityl-protected

  标题化合物是由 4,4-二甲氧基丁腈和各自的酯通过克莱森缩合和随后的 Paal-Knorr 吡咯合成以两步顺序制备的。该序列可以作为一锅程序进行，在两个步骤中以 47-72% 的产率提供吡咯（13 个例子）。该方法的分子内变体被应用于从各自的三苯甲基保护的ω-氨基链烷酸酯全合成丹那达和suffrutine A。
• Domino reaction sequences in the rhodium-catalyzed hydroformylation of 3-acetyl-1-allylpyrrole: a short route to 5,6,7,8-tetrahydroindolizines
  作者：Silvia Rocchiccioli、Roberta Settambolo、Raffaello Lazzaroni

  DOI：10.1016/j.jorganchem.2005.01.018

  日期：2005.3

  When 3-acetyl-l-allylpyrrole (1) was subjected under hydroformylation conditions, with Rh-4(CO)(12) as catalyst precursor, to 30 atm CO/H-2 (1:1) total pressure and 140 degrees C, an equimolar mixture of the isomeric 5,6,7,8-tetrahydroindolizines 4' and 5' was obtained as the almost exclusive product. In both cases a domino hydroformylation/cyclization on the alpha pyrrole positions by the aldehyde 3 carbonyl group occurs which involves different intermediates: while 4' is generated via the dihydroindolizine 4, 5' forms via direct reduction of 8-hydroxytetrahydroindolizine 5, a structure that has never been observed before from 1-allylpyrroles under oxo conditions. (c) 2005 Published by Elsevier B.V.