3-(2-ethoxy-vinyl)-furo[3,2-b]pyridine | 457865-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 3-(2-ethoxy-vinyl)-furo[3,2-b]pyridine
• 英文别名: 3-[(E)-2-ethoxyethenyl]furo[3,2-b]pyridine
• CAS: 457865-55-3
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: RHYGPDPQIQECFD-FNORWQNLSA-N

物化性质

• 沸点：
  304.8±27.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯酸乙酯 、 3-(2-ethoxy-vinyl)-furo[3,2-b]pyridine 以 四氢呋喃 为溶剂， 20.0 ℃ 、1200.02 MPa 条件下， 反应 48.0h， 以72%的产率得到8-ethoxy-5a,6,7,8-tetrahydrobenzo[4,5]furo[3,2-b]pyridine-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  New Carbanionic Access to 3-Vinylindoles and 3-Vinylbenzofurans

  摘要：

  [GRAPHICS]A simple route to 3-vinylbenzofurans, 3-vinyifuropyridines, and 3-vinylindoles from readily accessible acetylenic precursors is described. A standard halogen-lithium exchange triggers an irreversible! addition on the triple bond, according to a 5-exo-dig heterocyclization process, followed by a lithium ethoxide elimination. A final isomerization of the exocyclic allene provides a 1,3-dienic system that can react with acrylates, in thermal or hyperbaric conditions, to provide the expected [4+2] cycloadducts.

  DOI：

  10.1021/ol026351v
• 作为产物：
  描述：

  3-羟基-2-碘吡啶 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-(2-ethoxy-vinyl)-furo[3,2-b]pyridine
  参考文献：
  名称：

  New Carbanionic Access to 3-Vinylindoles and 3-Vinylbenzofurans

  摘要：

  [GRAPHICS]A simple route to 3-vinylbenzofurans, 3-vinyifuropyridines, and 3-vinylindoles from readily accessible acetylenic precursors is described. A standard halogen-lithium exchange triggers an irreversible! addition on the triple bond, according to a 5-exo-dig heterocyclization process, followed by a lithium ethoxide elimination. A final isomerization of the exocyclic allene provides a 1,3-dienic system that can react with acrylates, in thermal or hyperbaric conditions, to provide the expected [4+2] cycloadducts.

  DOI：

  10.1021/ol026351v

文献信息

• Access to Tri- and Tetracyclic Structures by Thermally Promoted and High-Pressure-Promoted [4+2] Cycloadditions of 2-, 3- or 4-Vinyl-Substituted Binuclear Heterocycles
  作者：Frédéric Le Strat、Hélène Vallette、Loïc Toupet、Jacques Maddaluno

  DOI：10.1002/ejoc.200500416

  日期：2005.12

  A set of 3-(2-alkoxyvinyl)benzofurans, -furopyridines and-indoles 5–8 have been tested in [4+2] cycloaddition reactions. The results indicate that they all behave as good dienes, even with only moderately activated dienophiles such as acrylates or MVK. The endo/exo selectivity observed in the adducts depends on the activation conditions: in general, thermal conditions tend to favour the exo isomers

  已在 [4+2] 环加成反应中测试了一组 3-(2-烷氧基乙烯基)苯并呋喃、-呋喃吡啶和-吲哚 5–8。结果表明它们都表现得像良好的二烯，即使只有适度活化的亲二烯体，如丙烯酸酯或 MVK。在加合物中观察到的内/外选择性取决于活化条件：通常，热条件倾向于有利于外型异构体，而高压优先提供内型异构体。只有这些二烯的 (E) 异构体被证明具有反应性，(Z) 异构体通常在未改变的情况下回收。[4.4.0] 双核杂环如异色烯化合物 13 和异喹啉酮 14-16 在这里测试证明是显着较低的反应性。最后，所得三环加合物 19 与 NPM 进行烯反应。发生仅涉及这些加合物的内异构体的加成，立体选择性地提供琥珀酰亚胺衍生物 29，尽管产率低。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• New Carbanionic Access to 3-Vinylindoles and 3-Vinylbenzofurans
  作者：Frédéric Le Strat、Jacques Maddaluno

  DOI：10.1021/ol026351v

  日期：2002.8.1

  [GRAPHICS]A simple route to 3-vinylbenzofurans, 3-vinyifuropyridines, and 3-vinylindoles from readily accessible acetylenic precursors is described. A standard halogen-lithium exchange triggers an irreversible! addition on the triple bond, according to a 5-exo-dig heterocyclization process, followed by a lithium ethoxide elimination. A final isomerization of the exocyclic allene provides a 1,3-dienic system that can react with acrylates, in thermal or hyperbaric conditions, to provide the expected [4+2] cycloadducts.