1-oxo-2-phenyl-1H-inden-3-yl prop-2-yn-1-yl carbonate | 1446518-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1-oxo-2-phenyl-1H-inden-3-yl prop-2-yn-1-yl carbonate
• CAS: 1446518-26-8
• 化学式: C₁₉H₁₂O₄
• 分子量: 304.302
• InChiKey: YBGFUDODXMCGHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-oxo-2-phenyl-1H-inden-3-yl prop-2-yn-1-yl carbonate 、 苯酚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以85%的产率得到2-(3-phenoxyprop-1-en-2-yl)-2-phenylcyclopentane-1,3-dione
  参考文献：
  名称：

  Catalytic Decarboxylative Alkenylation of Enolates

  摘要：

  A palladium-catalyzed decarboxylative alkenylation of stabilized enolates has been developed, which gives rise to alkenylated dicarbonyl products from enol carbonates regioselectively with concomitant installation of a quaternary all-carbon center. The broad scope of the reaction has been demonstrated by successfully utilizing a range of enolates and external phenol nucleophiles.

  DOI：

  10.1021/ol401729m
• 作为产物：
  描述：

  炔丙基氯甲酸酯 、 苯茚二酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以92%的产率得到1-oxo-2-phenyl-1H-inden-3-yl prop-2-yn-1-yl carbonate
  参考文献：
  名称：

  Catalytic Decarboxylative Alkenylation of Enolates

  摘要：

  A palladium-catalyzed decarboxylative alkenylation of stabilized enolates has been developed, which gives rise to alkenylated dicarbonyl products from enol carbonates regioselectively with concomitant installation of a quaternary all-carbon center. The broad scope of the reaction has been demonstrated by successfully utilizing a range of enolates and external phenol nucleophiles.

  DOI：

  10.1021/ol401729m

文献信息

• Catalytic Chemo- and Regioselective Coupling of 1,3-Dicarbonyls with <i>N</i>-Heterocyclic Nucleophiles
  作者：Miles Kenny、Daniel J. Kitson、Vilius Franckevičius

  DOI：10.1021/acs.joc.6b00731

  日期：2016.6.17

  compounds with indole, pyrrole, imidazole, and pyrazole nucleophiles via an allylic linker under neutral conditions is disclosed. This process enables the installation of an all-carbon quaternary center and new C–C and C–N bonds in a single operation. Despite the weakly acidic nature of N-heterocycles, the reactions proceed with good efficiency and complete regio- and chemoselectivity.

  公开了在中性条件下经由烯丙基连接体开发的脱羧钯催化的1，3-二羰基化合物与吲哚，吡咯，咪唑和吡唑亲核试剂的偶联。此过程可在一次操作中安装全碳四元中心以及新的C–C和C–N键。尽管N-杂环具有弱酸性，但反应仍能高效进行，并具有完全的区域选择性和化学选择性。
• Regioswitchable Palladium-Catalyzed Decarboxylative Coupling of 1,3-Dicarbonyl Compounds
  作者：Miles Kenny、Jeppe Christensen、Simon J. Coles、Vilius Franckevičius

  DOI：10.1021/acs.orglett.5b01979

  日期：2015.8.7

  A palladium-catalyzed chemo- and regioselective coupling of 1,3-dicarbonyl compounds via an allylic linker has been developed. This reaction, which displays broad substrate scope, forms two C-C bonds and installs two all-carbon quaternary centers. The regioselectivity of the reaction can be predictably controlled by utilizing an enol carbonate of one of the coupling partners.