2-amino-2′,5-dioxo-1′,2′,5,7-tetrahydrospiro[furo[3,4-b]pyran-4,3′-indole]-3-carbonitrile | 1208230-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-amino-2′,5-dioxo-1′,2′,5,7-tetrahydrospiro[furo[3,4-b]pyran-4,3′-indole]-3-carbonitrile
• 英文别名: 2-amino-2',5-dioxo-5,7-dihydrospiro[furo[3,4-b]pyran-4,3'-indoline]-3-carbonitrile；2-Amino-2',5-dioxo-5,7-dihydrospiro[furo[3,4-b]pyran-4,3'-indoline]-3-carbonitrile；2'-amino-2,5'-dioxospiro[1H-indole-3,4'-7H-furo[3,4-b]pyran]-3'-carbonitrile
• CAS: 1208230-55-0
• 化学式: C₁₅H₉N₃O₄
• 分子量: 295.254
• InChiKey: GGQQSSDPPLZJSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟乙酰乙酸内酯 、 5-硝基靛红 、 丙二腈 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到2-amino-2′,5-dioxo-1′,2′,5,7-tetrahydrospiro[furo[3,4-b]pyran-4,3′-indole]-3-carbonitrile
  参考文献：
  名称：

  Efficient Catalyst-Free One-Pot Three-Component Synthesis of Novel Spiro­oxindole Derivatives, and Their Cytotoxic Activities

  摘要：

  A simple and efficient one-pot approach for assembling novel spiro[indolepyranopyrrole] derivatives was developed and used to prepare a series of biologically important compounds. The reaction was easily performed with high efficiency under very simple and mild conditions without any catalysts and it gave good yields, avoiding time-consuming costly synthesis and laborious workup and purification of products. The cytotoxic activities of these new spiro[indolepyranopyrrole] derivatives were evaluated in vitro. Most of the tested compounds exhibited significant cytotoxicities to Raji cell lines.

  DOI：

  10.1055/s-0033-1341028

文献信息

• Efficient One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by <scp>l</scp>-Proline in Aqueous Medium
  作者：Yuling Li、Hui Chen、Chunling Shi、Daqing Shi、Shunjun Ji

  DOI：10.1021/cc9001185

  日期：2010.3.8

  An efficient one-pot synthesis of spirooxindole derivatives by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of l-proline is reported. This new protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, low cost, and convenient operation.

  据报道，在1-脯氨酸存在下，靛红，丙二腈（氰基乙酸酯）和1,3-二羰基化合物在水中的三组分反应可有效地一锅合成螺环吲哚衍生物。该新方案具有环境友好，产率高，反应时间短，成本低和操作方便的优点。
• Manganese ferrite nanoparticle catalyzed tandem and green synthesis of spirooxindoles
  作者：Ramin Ghahremanzadeh、Zahra Rashid、Amir-Hassan Zarnani、Hossein Naeimi

  DOI：10.1039/c4ra05756b

  日期：——

  PEG-400 as a nontoxic, green and reusable solvent was used for the synthesis of novel spiro-furo-pyridine-indoline-carbonitriles in the presence of a magnetically recoverable nanocatalyst.

  使用PEG-400作为无毒、绿色和可重复使用的溶剂，在具有可磁性回收的纳米催化剂存在下合成了新型螺环呋喃吡啶-吲哚-腈化合物。
• Efficient Catalyst-Free One-Pot Three-Component Synthesis of Novel Spiro­oxindole Derivatives, and Their Cytotoxic Activities
  作者：Jingchao Tao、Chao Han、Tao Zhang、Anqi Zhang、Dandan Wang、Weimin Shi

  DOI：10.1055/s-0033-1341028

  日期：——

  A simple and efficient one-pot approach for assembling novel spiro[indolepyranopyrrole] derivatives was developed and used to prepare a series of biologically important compounds. The reaction was easily performed with high efficiency under very simple and mild conditions without any catalysts and it gave good yields, avoiding time-consuming costly synthesis and laborious workup and purification of products. The cytotoxic activities of these new spiro[indolepyranopyrrole] derivatives were evaluated in vitro. Most of the tested compounds exhibited significant cytotoxicities to Raji cell lines.