2’-amino-1,3-dihydro-1,3,5’-trioxospiro[indene-2,4’-pyrano[3,2-c]chromene]-3’-carbonitrile | 1233925-25-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2’-amino-1,3-dihydro-1,3,5’-trioxospiro[indene-2,4’-pyrano[3,2-c]chromene]-3’-carbonitrile
• 英文别名: 2'-amino1,3,5'-trioxo-1,3-dihydro-5'H-spiro[indene-2,4'-pyrano[3,2-c]chromene]-3'-carbonitrile；2′-amino-1,3,5′-trioxo-5′H-spiro[indene-2,4′-[4′H]pyrano[3,2-c]chromene]-3′-carbonitrile；2'-Amino-1,3,5'-trioxospiro[indene-2,4'-pyrano[3,2-c]chromene]-3'-carbonitrile；2'-amino-1,3,5'-trioxospiro[indene-2,4'-pyrano[3,2-c]chromene]-3'-carbonitrile
• CAS: 1233925-25-1
• 化学式: C₂₁H₁₀N₂O₅
• 分子量: 370.321
• InChiKey: GZYDYQDDPAOGRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 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：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  水合茚三酮 以 乙醇 为溶剂， 反应 7.25h， 生成 2’-amino-1,3-dihydro-1,3,5’-trioxospiro[indene-2,4’-pyrano[3,2-c]chromene]-3’-carbonitrile
  参考文献：
  名称：

  One-pot of three-component synthesis of novel amino-spiroindene derivatives

  摘要：

  通过宁西特林、丙二腈或乙基氰基乙酸酯与包括1,2-和1,3-二羰基化合物/烯醇在内的各种试剂反应，实现了一种简便高效的一锅法三组分合成氨基螺吲哚衍生物。

  DOI：

  10.1007/s13738-013-0332-3

文献信息

• Na2EDTA: an efficient, green and reusable catalyst for the synthesis of biologically important spirooxindoles, spiroacenaphthylenes and spiro-2-amino-4H-pyrans under solvent-free conditions
  作者：Tayebeh Jazinizadeh、Malek Taher Maghsoodlou、Reza Heydari、Afshin Yazdani-Elah-Abadi

  DOI：10.1007/s13738-017-1148-3

  日期：2017.10

  For the first time, the organic salt Na2EDTA was used as a catalyst for an effective and facile preparation of spiro-4H-pyrans via single-pot three-component condensation of isatin/acenaphthoquinone/ninhydrin, malononitrile, and CH-acids through Knoevenagel–Michael–annulation sequence. This new protocol employing Na2EDTA, which is a green, recyclable, and inexpensive catalyst, offers advantages such

  第一次，将有机盐Na 2 EDTA用作催化剂，通过Isatin / ac萘醌/茚三酮，丙二腈和CH-酸的单锅三组分缩合反应，有效而便捷地制备spiro-4 H -pyrans通过Knoevenagel–Michael–环形序列。这项采用Na 2 EDTA的新方案是一种绿色，可回收且廉价的催化剂，具有无溶剂，高效反应条件，反应时间短（10-15分钟），后处理容易，收率高等优点。比其他环境合成方法更经济。
• Polystyrene@graphene oxide-Fe3O4 as a novel and magnetically recyclable nanocatalyst for the efficient multi-component synthesis of spiro indene derivatives
  作者：Seyedeh Fatemeh Hojati、Amirhassan Amiri、Maryam Mahamed

  DOI：10.1007/s11164-019-04021-w

  日期：2020.2

  (GO-Fe3O4) nanocomposite has been prepared and characterized by FT-IR, TEM and VSM techniques, and its catalytic activity has been evaluated in the multi-component synthesis of two series of indene derivatives. The three-component condensation of ninhydrin/isatin, malononitrile and active methylene-containing compounds and also the four-component condensation of ninhydrin, o-phenylenediamines, malononitrile

  制备了聚苯乙烯（PS）包覆的磁性氧化石墨烯（GO-Fe 3 O 4）纳米复合材料，并通过FT-IR，TEM和VSM技术对其进行了表征，并在两个系列的多组分合成中评估了其催化活性。茚衍生物。在PS @ GO-Fe存在下，令人满意地进行了茚三酮/靛红，丙二腈和含活性亚甲基的化合物的三组分缩合，以及茚三酮，邻苯二胺，丙二腈和含活性亚甲基的化合物的四组分缩合。3 O 4磁性纳米复合材料，以及相应的2'-氨基螺[indene-2,4'-吡喃] -3'-腈，2'-氨基螺[二氢吲哚-3、4'-吡喃] -3'-腈和2' -aminospiro [indeno [1,2-分别以良好至优异的产率获得了b ]喹喔啉-11,4'-吡喃] -3'-腈。与所报道的方法相比，反应时间非常短，易于后处理程序以及催化剂的易于分离和可重复使用性是当前方法的显着优势。
• 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
• A Simple Three-Component Synthesis of Spiro-Pyran Derivatives
  作者：Yi He、Hongyun Guo、Jinjin Tian

  DOI：10.3184/174751911x13149692358913

  日期：2011.9

  A series of spiro-pyran derivatives have been synthesised by a three-component reaction of ninhydrin or acenaphthenequinone, malononitrile and 1,3-dicarbonyl compounds such as cyclohexane-1,3-dione, dimedone and barbituaric acid in ethanol with NaHCO₃as the catalyst. This method has the advantages of easy work-up, mild reaction condition, high yields and it is cheap.

  以 NaHCO3 为催化剂，在乙醇中通过茚三酮或苊醌、丙二腈和 1,3-二羰基化合物（如环己烷-1,3-二酮、二美酮和巴比妥酸）的三组分反应合成了一系列螺吡喃衍生物。这种方法具有操作简便、反应条件温和、产率高和成本低廉等优点。
• 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。