6'-amino-3',5-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile

• 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: 6'-amino-3',5-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 英文别名: 6'-amino-3',5-dimethyl-2-oxospiro[1H-indole-3,4'-2H-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 化学式: C₁₆H₁₃N₅O₂
• 分子量: 307.312
• InChiKey: JGBLKBJRYMHCPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-methyl-3-dicyanomethylene-2H-indole-2-one 、 3-甲基-2-吡唑啉-5-酮 在 三乙醇胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以48%的产率得到6'-amino-3',5-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
  参考文献：
  名称：

  Synthesis and molecular structure of spirocyclic 2-oxindole derivatives of 2-amino-4H-pyran condensed with the pyrazolic nucleus

  摘要：

  4,3'-Spiro[(6-amino-5-R-3-methyl-2H,4H-pyrano[2,3-c]pyrazolo)-2'-oxindoles] were synthesized based on the three-component condensation of isatins with 3-methyl-pyrazolone-5 and respective methylene active nitriles in the presence of basic catalysts. The molecular structure of the resulting compounds was proved unambiguously by X-ray diffraction. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.050

文献信息

• Meglumine promoted one-pot, four-component synthesis of pyranopyrazole derivatives
  作者：Rui-Yun Guo、Zhi-Min An、Li-Ping Mo、Shu-Tao Yang、Hong-Xia Liu、Shu-Xia Wang、Zhan-Hui Zhang

  DOI：10.1016/j.tet.2013.09.082

  日期：2013.11

  catalyst for the synthesis of a series of pyranopyrazole derivatives via a one-pot, four-component reaction of carbonyl compound or isatin, hydrazine hydrate, malononitrile, and β-keto ester in EtOH–H2O. The catalyst was found to work extremely for aldehydes, ketones or isatins at room temperature to give the corresponding dihydropyrano[2,3-c]pyrazole or spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives

  证明葡甲胺是一种生物基化学物质，它是通过羰基化合物或靛红，水合肼，丙二腈和β的单锅四组分反应合成一系列吡喃并吡唑衍生物的高效且可重复使用的催化剂。酮的EtOH-H酯2 O.将催化剂在室温下发现极其对醛，酮或靛红工作以得到相应的二氢吡喃并[2,3- c ^ ]吡唑或螺[二氢吲哚-3,4'-吡喃并并[2,3- c ^ ]吡唑]衍生物以高产率。这个新方法的显着特点是广泛的底物范围，室温下的反应条件，反应时间短，产量高，容易进行后处理过程中，催化剂的可重用性，并且不存在有害的有机溶剂。
• Green synthesis of tetrahydrobenzo[b]pyrans, pyrano[2,3-c]pyrazoles and spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles catalyzed by nano-structured diphosphate in water
  作者：Behrooz Maleki、Negar Nasiri、Reza Tayebee、Amir Khojastehnezhad、Hossien Ali Akhlaghi

  DOI：10.1039/c6ra15800e

  日期：——

  A green and recoverable nano-structured diphosphate (Na2CaP2O7) was synthesized and fully characterized using FT-IR spectra, X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and energy-dispersive X-ray spectroscopy (EDX) analysis. The...

  合成了绿色且可回收的纳米结构二磷酸盐（Na2CaP2O7），并使用FT-IR光谱，X射线衍射图（XRD），扫描电子显微镜（SEM）和能量色散X射线光谱（EDX）分析对其进行了全面表征。这...
• Green Access to Multi-Component Synthesis of Spiropyranopyrazoles
  作者：D. Pore、P. Hegade、D. Gaikwad、P. Patil、J. Patil

  DOI：10.2174/15701786113106660069

  日期：2014.1.31

  A catalyst-free multi-component synthesis of spiro[indoline-3,4’-pyrano[2,3-c]pyrazoles] is reported from in situ formed pyrazolone by exothermic reaction of ethyl acetoacetate with hydrazine hydrate, isatin and malononitrile in water at room temperature. A suggested mechanistic approach was supported by semi-empirical calculations. The transformation is carried out in water alone and thus achieved the highest level of green chemistry. Simple reaction conditions, easy work-up procedure and isolation of products are the auxiliary advantages of present protocol.

  报告了一种无催化剂多组分合成螺[吲哚啉-3,4'-吡喃并[2,3-c]吡唑]的方法，该方法通过乙酰乙酸乙酯与水合肼、异atin 和丙二腈在室温水中的放热反应，从原位形成的吡唑酮中合成螺[吲哚啉-3,4'-吡喃并[2,3-c]吡唑]。半经验计算支持了建议的机理方法。该转化过程仅在水中进行，因此达到了绿色化学的最高水平。简单的反应条件、简便的操作步骤和产物的分离是本方案的辅助优势。
• Chitosan/ionic liquid forms a renewable and reusable catalyst system used for the synthesis of highly functionalized spiro derivatives
  作者：Pratibha Rai、Madhulika Srivastava、Jaya Singh、Jagdamba Singh

  DOI：10.1039/c3nj01545a

  日期：——

  Chitosan, a reusable heterogeneous catalyst, can be combined with an ionic liquid as a green solvent to generate a highly efficient catalyst system for our densely functionalised and diversified target molecule. The reaction is completed with a good to excellent yield. This procedure demonstrates an eco-friendly catalyst system and eliminates the use of toxic transition metal catalysts, bases and volatile organic solvents, which adversely affect the environment and human beings.

  壳聚糖是一种可重复使用的异相催化剂，可与作为绿色溶剂的离子液体结合，生成一种高效的催化剂体系，用于我们的密集官能化和多样化目标分子。反应完成后，可获得良好甚至极佳的收率。该过程展示了一种生态友好型催化剂体系，避免了使用有毒的过渡金属催化剂、碱和挥发性有机溶剂，这些物质会对环境和人类造成不利影响。
• Novel and Efficient One-Pot Synthesis of Spiro[Indoline-3,4′-Pyrano [2,3-c]pyrazole]Derivatives Catalysed by L-Proline in Aqueous Medium
  作者：Jiangxia Yu、Yongbing Zhou、Tianhua Shen、Wengang Mao、Kang Chen、Qingbao Song

  DOI：10.3184/174751913x13687116634925

  日期：2013.6

  An efficient mild one-pot synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole derivatives by a four-component reaction of hydrazine, a β-keto ester, isatin, and malononitrile catalysed by L-proline in water is reported.

  在 L-脯氨酸的催化下，通过肼、β-酮酯、异atin 和丙二腈在水中的四组分反应，报道了一种高效温和的螺[吲哚啉-3,4′-吡喃并[2,3-c]吡唑衍生物的一锅合成方法。