2-amino-6,7-dihydro-5-oxocyclopenta[b]pyran-3,4,4(5H)-tricarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-amino-6,7-dihydro-5-oxocyclopenta[b]pyran-3,4,4(5H)-tricarbonitrile
• 英文别名: 2-Amino-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyran-3,4,4-tricarbonitrile；2-amino-5-oxo-6,7-dihydrocyclopenta[b]pyran-3,4,4-tricarbonitrile
• 化学式: C₁₁H₆N₄O₂
• mdl: MFCD03766778
• 分子量: 226.194
• InChiKey: LZHIAJOVHBSVSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-环戊二酮 、 四氰基乙烯 在 pyridine-functionalized mesoporous molecular sieves MCM-41 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-amino-6,7-dihydro-5-oxocyclopenta[b]pyran-3,4,4(5H)-tricarbonitrile
  参考文献：
  名称：

  Pyridine-Functionalized MCM-41 as an Efficient and Recoverable Catalyst for the Synthesis of Pyran Annulated Heterocyclic Systems

  摘要：

  介绍了吡啶功能化 MCM-41 催化四氰基乙烯与各种活化 CH 酸化合物之间的反应。这些反应可在室温下几分钟内以高产率获得相应的吡喃环状杂环系统。反应过程非常简单，产物无需进一步纯化。催化剂可以多次循环和重复使用，而不会出现明显的性能损失。

  DOI：

  10.1248/cpb.58.270

文献信息

• Isocyanide‐Catalyzed Reaction of Tetracyanoethylene and Activated 1,3‐Dicarbonyl CH‐Acid Compounds: A Rapid and Efficient Synthesis of Pyran Annulated Heterocyclic Systems
  作者：Ahmad Shaabani、Ali Hossein Rezayan、Afshin Sarvary、Abbas Rahmati

  DOI：10.1080/00397910701749757

  日期：2008.1

  Abstract An isocyanide‐catalyzed reaction between tetracyanoethylene and various activated CH‐acid compounds to afford the corresponding pyran annulated heterocyclic ring systems, in high yield at room temperature within a few minutes, is described. To the best of our knowledge, this is the first example in which isocyanide functions as only a catalyst but not a reagent.

  摘要描述了四氰基乙烯与各种活化的 CH-酸化合物之间的异氰化物催化反应，以在室温下几分钟内以高产率提供相应的吡喃成环杂环系统。据我们所知，这是第一个异氰化物仅作为催化剂而不作为试剂起作用的例子。
• Pyridine-Functionalized MCM-41 as an Efficient and Recoverable Catalyst for the Synthesis of Pyran Annulated Heterocyclic Systems
  作者：Ahmad Shaabani、Mostafa Mohammadpour Amini、Sabrieh Ghasemi、Rahim Ghadari、Ali Hossein Rezayan、Yousef Fazaeli、Shahzad Feizi

  DOI：10.1248/cpb.58.270

  日期：——

  Pyridine-functionalized MCM-41 catalyzed reactions between tetracyanoethylene and various activated CH-acid compounds are described. These reactions afford the corresponding pyran annulated heterocyclic ring systems in high yields at room temperature within a few minutes. The work-up procedure is very simple and the products do not require further purification. The catalyst can be recycled and reused for several times without observable loss of performance.

  介绍了吡啶功能化 MCM-41 催化四氰基乙烯与各种活化 CH 酸化合物之间的反应。这些反应可在室温下几分钟内以高产率获得相应的吡喃环状杂环系统。反应过程非常简单，产物无需进一步纯化。催化剂可以多次循环和重复使用，而不会出现明显的性能损失。
• TiO2 and TiO2 nanoparticles as efficient and recoverable catalysts for the synthesis of pyran annulated heterocyclic systems
  作者：Nasser Babakhani、Sajjad Keshipoor

  DOI：10.1007/s11164-012-0766-8

  日期：2013.7

  affords the corresponding pyran annulated heterocyclic systems in high yields at room temperature in 3 h. The work-up procedure is very simple, and the products do not require further purification. The catalysts can be recycled and reused several times without observable loss of performance. Graphical abstract

  摘要 描述了各种活化的CH-酸和四氰基乙烯之间的TiO 2催化反应。该反应在室温下3小时内以高收率提供了相应的吡喃环化的杂环系统。后处理程序非常简单，产品不需要进一步纯化。催化剂可以循环使用多次，而不会出现性能损失。 图形概要