ethyl 2-(2,3-dihydro-1H-indolizin-4-ium-3-yl)acetate;trifluoromethanesulfonate | 1289053-60-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: ethyl 2-(2,3-dihydro-1H-indolizin-4-ium-3-yl)acetate;trifluoromethanesulfonate
• CAS: 1289053-60-6
• 化学式: CF₃O₃S*C₁₂H₁₆NO₂
• 分子量: 355.335
• InChiKey: XAJBYERCBRDULE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2,3-dihydro-1H-indolizin-4-ium-3-yl)acetate;trifluoromethanesulfonate 在 palladium 10% on activated carbon 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 5-(吡啶-2-基)戊酸乙酯
  参考文献：
  名称：

  Aerobic Pd-Catalyzed sp³ C−H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes

  摘要：

  This communication describes a new method for the Pd/polrxometalate-catalyzed aerobic olefination of unactivated sp(3)C H bonds. Nitrogen heterocycles serve as directing groups, and air is used as the terminal oxidant. The products undergo reversible intramolecular Michael addition, which protects the monoalkenylated product from overfunctionalization. Hydrogenation of the Michael adducts provides access to bicyclic nitrogen-containing scaffolds that are prevalent in alkaloid natural products. Additionally, the cationic Michael adducts undergo facile elimination to release alpha,beta-unsaturated olefins, which can be further elaborated via C-C and C-heteroatom bond-forming reactions.

  DOI：

  10.1021/ja2015586
• 作为产物：
  描述：

  2-乙基吡啶 、 三氟甲磺酸钠 、 丙烯酸乙酯 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 作用下， 以 溶剂黄146 为溶剂， 反应 18.0h， 以89%的产率得到ethyl 2-(2,3-dihydro-1H-indolizin-4-ium-3-yl)acetate;trifluoromethanesulfonate
  参考文献：
  名称：

  Aerobic Pd-Catalyzed sp³ C−H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes

  摘要：

  This communication describes a new method for the Pd/polrxometalate-catalyzed aerobic olefination of unactivated sp(3)C H bonds. Nitrogen heterocycles serve as directing groups, and air is used as the terminal oxidant. The products undergo reversible intramolecular Michael addition, which protects the monoalkenylated product from overfunctionalization. Hydrogenation of the Michael adducts provides access to bicyclic nitrogen-containing scaffolds that are prevalent in alkaloid natural products. Additionally, the cationic Michael adducts undergo facile elimination to release alpha,beta-unsaturated olefins, which can be further elaborated via C-C and C-heteroatom bond-forming reactions.

  DOI：

  10.1021/ja2015586

文献信息

• Aerobic Pd-Catalyzed sp³ C−H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes
  作者：Kara J. Stowers、Kevin C. Fortner、Melanie S. Sanford

  DOI：10.1021/ja2015586

  日期：2011.5.4

  This communication describes a new method for the Pd/polrxometalate-catalyzed aerobic olefination of unactivated sp(3)C H bonds. Nitrogen heterocycles serve as directing groups, and air is used as the terminal oxidant. The products undergo reversible intramolecular Michael addition, which protects the monoalkenylated product from overfunctionalization. Hydrogenation of the Michael adducts provides access to bicyclic nitrogen-containing scaffolds that are prevalent in alkaloid natural products. Additionally, the cationic Michael adducts undergo facile elimination to release alpha,beta-unsaturated olefins, which can be further elaborated via C-C and C-heteroatom bond-forming reactions.