2-amino-4-(3-nitrophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile | 1266549-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-(3-nitrophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile
• 英文别名: 2-amino-4-(3-nitrophenyl)-5-oxo-6,7-dihydro-4H-cyclopenta[b]pyran-3-carbonitrile
• CAS: 1266549-84-1
• 化学式: C₁₅H₁₁N₃O₄
• 分子量: 297.27
• InChiKey: QQLRRNYNTXLKJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  122
• 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 、 3-(2,2-二氰基乙烯基)-N-羟基苯胺氧化物 反应 3.0h， 生成 2-amino-4-(3-nitrophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile
  参考文献：
  名称：

  Design and an efficient synthesis of natural product-based cyclopenta[b]pyran derivatives with potential bioactivity

  摘要：

  A series of 4-aryl-cyclopenta[b]pyran derivatives, designed based on natural product scaffold, were synthesized efficiently via multi-component reaction under solvent-free and catalyst-free conditions. This chemistry provides a new compound library with potential activity for biomedical screening. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.09.076

文献信息

• 1,8-Diazabicyclo[5.4.0]undec-7-ene: A Highly Efficient Catalyst for One-Pot Synthesis of Substituted Tetrahydro-4<i>H</i>-chromenes, Tetrahydro[<i>b</i>]pyrans, Pyrano[<i>d</i>]pyrimidines, and 4<i>H</i>-Pyrans in Aqueous Medium
  作者：Jitender M. Khurana、Bhaskara Nand、Pooja Saluja

  DOI：10.1002/jhet.1507

  日期：2014.5

  We have reported 1,8‐diazabicyclo[5.4.0]undec‐7‐ene catalyzed one‐pot synthesis of tetrahydro‐4H‐chromenes, tetrahydro[b]pyrans, pyrano[d]pyrimidines and 4H‐pyrans from aldehydes, active methylene compounds malononitrile/ethyl cyanocacetate and activated C–H acids such as dimedone, 1,3‐cyclohexanedione, 1,3‐cyclopentanedione, 1,3‐dimethylbarbituric acid, and ethyl acetoacetate in water under reflux

  我们已经报道了1,8-二氮杂双环[5.4.0]十一碳-7烯从醛催化一锅合成四氢-4 H-苯甲基，四氢[ b ]吡喃，吡喃并[ d ]嘧啶和4 H-吡喃。活性亚甲基化合物丙二腈/氰基乙酸乙酯和活化的C-H酸，如二甲酮，1,3-环己二酮，1,3-环戊烷二酮，1,3-二甲基巴比妥酸和乙酰乙酸乙酯在水中回流。该方法的吸引人的特征是温和的反应条件，反应介质的可重​​复使用性，较短的反应时间，易于分离的产物以及优异的产率。版权所有©2013 HeteroCorporation
• Nickel Nanoparticles as Semiheterogeneous Catalyst for One-Pot, Three-Component Synthesis of 2-Amino-4<i>H</i>-pyrans and Pyran Annulated Heterocyclic Moieties
  作者：Jitender M. Khurana、Kanika Vij

  DOI：10.1080/00397911.2012.700474

  日期：2013.9.2

  An efficient route for the synthesis of 2-amino-4H-pyrans and pyran annulated heterocyclic moieties has been reported via one-pot tandem Knoevenagel-cyclocondensation of aldehydes, malononitrile, and carbocyclic/heterocyclic 1,3-diones in the presence of stabilized nickel nanoparticles in ethylene glycol at room temperature. A wide range of aromatic aldehydes undergo the condensation readily to afford the pharmacologically important compounds in excellent yields. Bis-pyranization has been observed in the reactions of terephthaldehyde. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.