7'-amino-2,4'-dioxo-2'-thioxo-1',2',3',4'-tetrahydro-2H-spiro[acenaphthylene-1,5'-pyrano[2,3-d]pyrimidine]-6'-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: 7'-amino-2,4'-dioxo-2'-thioxo-1',2',3',4'-tetrahydro-2H-spiro[acenaphthylene-1,5'-pyrano[2,3-d]pyrimidine]-6'-carbonitrile
• 英文别名: 7-amino-2',4-dioxo-2-sulfanylidenespiro[1H-pyrano[2,3-d]pyrimidine-5,1'-acenaphthylene]-6-carbonitrile
• 化学式: C₁₉H₁₀N₄O₃S
• 分子量: 374.379
• InChiKey: KSTJHUGYILEACW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 丙二腈 、 苊醌 在 mesoporous silica SBA-15 supported 1,4-diazabicyclo[2.2.2]octane 作用下， 以 水 为溶剂， 反应 0.17h， 以91%的产率得到7'-amino-2,4'-dioxo-2'-thioxo-1',2',3',4'-tetrahydro-2H-spiro[acenaphthylene-1,5'-pyrano[2,3-d]pyrimidine]-6'-carbonitrile
  参考文献：
  名称：

  Immobilization of 1,4-Diazabicyclo[2.2.2]Octane (DABCO) over Mesoporous Silica SBA-15: An Efficient Approach for the Synthesis of Functionalized Spirochromenes

  摘要：

  Immobilized 1,4-diazabicyclo[2.2.2]octane (DABCO) over mesoporous silica SBA-15 has been found to be an efficient heterogeneous base catalyst for the synthesis of biologically active functionalized spirochromene derivatives via three-component reaction of isatins/acenaphthoquinone, activated methylene reagents, and 1,3-dicarbonyl compounds in aqueous media. This ecofriendly protocol offers several advantages such as a cost-effective procedure with excellent yield, short reaction time, simple workup, recovery and reusability of catalyst, good functional group tolerance, and broad scope of usable substrates. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.789527

文献信息

• Immobilization of 1,4-Diazabicyclo[2.2.2]Octane (DABCO) over Mesoporous Silica SBA-15: An Efficient Approach for the Synthesis of Functionalized Spirochromenes
  作者：Robabeh Baharfar、Razieh Azimi

  DOI：10.1080/00397911.2013.789527

  日期：2014.1.2

  Immobilized 1,4-diazabicyclo[2.2.2]octane (DABCO) over mesoporous silica SBA-15 has been found to be an efficient heterogeneous base catalyst for the synthesis of biologically active functionalized spirochromene derivatives via three-component reaction of isatins/acenaphthoquinone, activated methylene reagents, and 1,3-dicarbonyl compounds in aqueous media. This ecofriendly protocol offers several advantages such as a cost-effective procedure with excellent yield, short reaction time, simple workup, recovery and reusability of catalyst, good functional group tolerance, and broad scope of usable substrates. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]