1-ethoxycarbonyl-2,9b-dihydro-1H-cyclopenta[c]chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 1-ethoxycarbonyl-2,9b-dihydro-1H-cyclopenta[c]chromen-4-one
• 英文别名: ethyl (1S,9bS)-4-oxo-2,9b-dihydro-1H-cyclopenta[c]chromene-1-carboxylate
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: HWKBHNBHNIRPSM-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(β-ethoxycarbonyl)styrenyl allenoate 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以96%的产率得到1-ethoxycarbonyl-2,9b-dihydro-1H-cyclopenta[c]chromen-4-one
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins

  摘要：

  [GRAPHICS]2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.

  DOI：

  10.1021/ol071181d

文献信息

• Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins
  作者：Christopher E. Henry、Ohyun Kwon

  DOI：10.1021/ol071181d

  日期：2007.8.1

  [GRAPHICS]2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.