2-amino-5-oxo-4-(thiophen-2-yl)-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile | 1266549-91-0

• 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-5-oxo-4-(thiophen-2-yl)-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile
• CAS: 1266549-91-0
• 化学式: C₁₃H₁₀N₂O₂S
• 分子量: 258.301
• InChiKey: UUFBMUTWWFGEEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.11
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1,3-环戊二酮 、 (2-噻吩亚甲基)甲烷-1,1-二甲腈 反应 5.0h， 生成 2-amino-5-oxo-4-(thiophen-2-yl)-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

• Base free synthesis of iron oxide supported on boron nitride for the construction of highly functionalized pyrans and spirooxindoles
  作者：Aniruddha Molla、Sahid Hussain

  DOI：10.1039/c5ra21969h

  日期：——

  BN@Fe₃O₄ network was synthesized via chemical reduction followed by aerial oxidation in absence of base and was subsequently used for the synthesis of highly functionalized pyrans and spirooxindoles derivatives on water.

  BN@Fe₃O₄网络是通过化学还原后在无碱的条件下进行空气氧化合成的，并随后用于在水中合成高度功能化的吡喃和螺环氧吲哚衍生物。
• Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles
  作者：Aniruddha Molla、Ezaz Hossain、Sahid Hussain

  DOI：10.1039/c3ra43514h

  日期：——

  A collection of pyrano[3,2-c] chromene, 4H-chromene and 4H-pyran were synthesized in excellent yield employing an innocuous, inexpensive and naturally occurring borax-catalyzed multicomponent domino reaction. The present protocol offers advantages in terms of higher yields, short reactions time and no workup and no column chromatography.

  利用一种无害、廉价和天然存在的硼砂催化多组分多米诺反应，合成了一系列吡喃并[3,2-c] 色烯、4H-色烯和 4H-吡喃，收率极高。本方案具有产率高、反应时间短、无需操作和柱层析等优点。
• 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.