2'-amino-7'-methyl-2,5'-dioxo-2H,5'H-spiro[acenaphthylene-1,4'-pyrano-[4,3-b]pyran]-3'-carbonitrile | 1370639-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2'-amino-7'-methyl-2,5'-dioxo-2H,5'H-spiro[acenaphthylene-1,4'-pyrano-[4,3-b]pyran]-3'-carbonitrile
• 英文别名: 2'-Amino-7'-methyl-2,5'-dioxospiro[acenaphthylene-1,4'-pyrano[4,3-b]pyran]-3'-carbonitrile；2'-amino-7'-methyl-2,5'-dioxospiro[acenaphthylene-1,4'-pyrano[4,3-b]pyran]-3'-carbonitrile
• CAS: 1370639-33-0
• 化学式: C₂₁H₁₂N₂O₄
• 分子量: 356.337
• InChiKey: NGNCUCNBAIYJAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 丙二腈 、 苊醌 在 1,1'-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 以97%的产率得到2'-amino-7'-methyl-2,5'-dioxo-2H,5'H-spiro[acenaphthylene-1,4'-pyrano-[4,3-b]pyran]-3'-carbonitrile
  参考文献：
  名称：

  一种新型碱性离子液体的引入，用于高效合成螺-4H-吡喃

  摘要：

  摘要 本研究合成了 1,1'-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) 氢氧化物作为一种含有双碱性功能的有效碱性离子液体。报告组。在使用 FT-IR、1H NMR、13C NMR 和质量分析进行表征后，该试剂可有效地用于通过多米诺 Knoevenagel/Michael/环化序列的一锅三组分缩合促进螺-4H-吡喃的合成。该方法的吸引人的特点是程序简单、反应时间短、产率高、无需柱色谱分离、原料可商业化、催化剂可回收利用。

  DOI：

  10.1016/j.molliq.2016.10.093

文献信息

• One-Pot Synthesis of Biologically Important Spiro-2-amino-4<i>H</i>-pyrans, Spiroacenaphthylenes, and Spirooxindoles Using DBU as a Green and Recyclable Catalyst in Aqueous Medium
  作者：Pooja Saluja、Komal Aggarwal、Jitender M. Khurana

  DOI：10.1080/00397911.2012.760130

  日期：2013.12.17

  Abstract We have reported DBU-catalyzed one-pot synthesis of biologically and pharmacologically important spiropyrans from condensation of malononitrile/ethyl cyanoacetate, 1,3-dicarbonyl compounds, and ninhydrin/acenaphthequinone/istain in good yields. This new protocol employing DBU, which is a green, recyclable, and inexpensive catalyst, offers advantages such as mild reaction conditions, short

  摘要 我们已经报道了 DBU 催化从丙二腈/氰基乙酸乙酯、1,3-二羰基化合物和茚三酮/苊醌/伊斯坦酮缩合合成具有生物学和药理学意义的螺吡喃，收率良好。这种采用 DBU 的新方案是一种绿色、可回收且价格低廉的催化剂，具有反应条件温和、反应时间短和易于分离产物等优点。这些结构已通过 X 射线分析得到证实。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• Highly Monodispersed PEG-stabilized Ni Nanoparticles: Proficient Catalyst for the Synthesis of Biologically Important Spiropyrans
  作者：Jitender M. Khurana、Sneha Yadav

  DOI：10.1071/ch11444

  日期：——

  A convenient and efficient synthesis of biologically and pharmacologically important spiropyrans from the condensation of malononitrile, 1,3-dicarbonyl compounds and ninhydrin/acenaphthequinone/isatin has been reported using recyclable heterogeneous polyethylene glycol (PEG)-stabilized Ni nanoparticles in ethylene glycol. This new protocol affords products in high yields and less reaction time.

  据报道，利用乙二醇中可回收的异质聚乙二醇（PEG）稳定镍纳米粒子，可以方便、高效地从丙二腈、1,3-二羰基化合物和茚三酮/苊醌/靛红的缩合物中合成具有重要生物和药理作用的螺旋吡喃。这一新方案可提供产率高、反应时间短的产品。
• Introduction of a novel basic ionic liquid containing dual basic functional groups for the efficient synthesis of spiro-4H-pyrans
  作者：Omid Goli-Jolodar、Farhad Shirini、Mohadeseh Seddighi

  DOI：10.1016/j.molliq.2016.10.093

  日期：2016.12

  Abstract In this research the synthesis of 1,1′-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) hydroxide as an effective basic ionic liquid containing dual basic functional groups is reported. After characterization using FT-IR, 1H NMR, 13C NMR and mass analyses, this reagent is efficiently used for promotion of the synthesis of spiro-4H-pyrans via one-pot three-component condensation through a

  摘要 本研究合成了 1,1'-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) 氢氧化物作为一种含有双碱性功能的有效碱性离子液体。报告组。在使用 FT-IR、1H NMR、13C NMR 和质量分析进行表征后，该试剂可有效地用于通过多米诺 Knoevenagel/Michael/环化序列的一锅三组分缩合促进螺-4H-吡喃的合成。该方法的吸引人的特点是程序简单、反应时间短、产率高、无需柱色谱分离、原料可商业化、催化剂可回收利用。
• The amino side chains do matter: chemoselectivity in the one-pot three-component synthesis of 2-amino-4H-chromenes by supramolecular catalysis with amino-appended β-cyclodextrins (ACDs) in water
  作者：Yufeng Ren、Bo Yang、Xiali Liao

  DOI：10.1039/c5cy01888a

  日期：——

  In this study, the one-pot three-component synthesis of 2-amino-4H-chromenes was accomplished by supramolecular catalysis using a series of well-designed amino-appended β-cyclodextrins (ACDs) in water. The catalytic mechanism was elucidated in detail with 1D and 2D NMR and ESI-MS analyses, while the key roles of amino side chains of ACDs in the reaction chemoselectivity were addressed for the first

  在这项研究中，使用一系列精心设计的氨基附加β-环糊精（ACD）通过超分子催化，完成了2-氨基-4 H-色烯的一锅三组分合成。通过1D和2D NMR和ESI-MS分析详细阐明了催化机理，同时首次探讨了ACD氨基侧链在反应化学选择性中的关键作用。
• General non-catalytic approach to spiroacenaphthylene heterocycles: multicomponent assembling of acenaphthenequinone, cyclic CH-acids and malononitrile
  作者：Michail N. Elinson、Alexey I. Ilovaisky、Valentina M. Merkulova、Pavel A. Belyakov、Fructuoso Barba、Belen Batanero

  DOI：10.1016/j.tet.2012.05.005

  日期：2012.7

  The new type of non-catalytic cascade reaction was found: the direct multicomponent reaction of acenaphthenequinone, cyclic CH-acids, and malononitrile to form spiroacenaphthylene heterocycles. The direct heating in water acenaphthenequinone, cyclic CH-acids, and malononitrile at 80 degrees C results in the formation of spiroacenaphthylene heterocycles in 90-95% yields. Thus, a new simple and efficient green 'one-pot' method to synthesize substituted spiroacenaphthylene frameworks was found directly from simple starting compounds. The application of this convenient green multicomponent method is also beneficial from the viewpoint of diversity-oriented large-scale processes. (C) 2012 Elsevier Ltd. All rights reserved.