9-(4-amino-2-oxo-2H-chromen-3-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one | 1441019-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(4-amino-2-oxo-2H-chromen-3-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 9-(4-amino-2-oxochromen-3-yl)-3,3-dimethyl-4,9-dihydro-2H-xanthen-1-one
• CAS: 1441019-16-4
• 化学式: C₂₄H₂₁NO₄
• 分子量: 387.435
• InChiKey: JPGCGJQIFACSDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氨基-苯并吡喃-2-酮 、 水杨醛 、 5,5-二甲基-1,3-环己二酮 在 zinc(II) oxide 作用下， 以 水 为溶剂， 反应 0.75h， 以90%的产率得到9-(4-amino-2-oxo-2H-chromen-3-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  Nanocrystalline and Reusable ZnO Catalyst for the Assembly of Densely Functionalized 4H-Chromenes in Aqueous Medium via One-Pot Three Component Reactions: A Greener “NOSE” Approach

  摘要：

  An ecofriendly, One-pot, three component ZnO nanoparticles-mediated synthesis of 4H-chromene in water under thermal condition has been described. The highly product-selective three component electrophilic reaction of 2-hydroxybenzaldehyde with an active methylene compound and another carbon-based varied nature of nucleophile has been developed by a reversible alkylation procedure using greener "NOSE" approach. Greenness of the process was well instituted, as water was used both;as reaction media as well as medium for the synthesis of catalyst. In these reactions, the use of nano-ZnO as a catalyst was documented to be crucial for rendering the reactions possible in water media, while replacing nano-ZnO with other acids or bases resulted in the generation of too many side products. The catalyst can be efficiently recycled up to the sixth run, an essential point in the area of green chemistry. The methodology provides cleaner conversion, shorter reaction times, and high selectivity, which make the protocol globally putative. The crystal structures of 4H-chromene, easily produced by a chromatography-free highly product-selective reaction, were explored by means of single crystal X-ray diffraction analysis, and H-bonding arrangements of one signified compound prepared is presented. In optimized mild conditions, the isolated yields are 86-93%.

  DOI：

  10.1021/jo400763z

文献信息

• Nanocrystalline and Reusable ZnO Catalyst for the Assembly of Densely Functionalized 4<i>H</i>-Chromenes in Aqueous Medium via One-Pot Three Component Reactions: A Greener “NOSE” Approach
  作者：Partha Pratim Ghosh、Asish R. Das

  DOI：10.1021/jo400763z

  日期：2013.6.21

  An ecofriendly, One-pot, three component ZnO nanoparticles-mediated synthesis of 4H-chromene in water under thermal condition has been described. The highly product-selective three component electrophilic reaction of 2-hydroxybenzaldehyde with an active methylene compound and another carbon-based varied nature of nucleophile has been developed by a reversible alkylation procedure using greener "NOSE" approach. Greenness of the process was well instituted, as water was used both;as reaction media as well as medium for the synthesis of catalyst. In these reactions, the use of nano-ZnO as a catalyst was documented to be crucial for rendering the reactions possible in water media, while replacing nano-ZnO with other acids or bases resulted in the generation of too many side products. The catalyst can be efficiently recycled up to the sixth run, an essential point in the area of green chemistry. The methodology provides cleaner conversion, shorter reaction times, and high selectivity, which make the protocol globally putative. The crystal structures of 4H-chromene, easily produced by a chromatography-free highly product-selective reaction, were explored by means of single crystal X-ray diffraction analysis, and H-bonding arrangements of one signified compound prepared is presented. In optimized mild conditions, the isolated yields are 86-93%.