4-(6-chloro-2-(methylamino)-3-nitro-4H-chromen-4-yl)-3-methyl-1H-pyrazol-5-ol | 1585971-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(6-chloro-2-(methylamino)-3-nitro-4H-chromen-4-yl)-3-methyl-1H-pyrazol-5-ol
• 英文别名: 4-[6-chloro-2-(methylazaniumyl)-3-nitro-4H-chromen-4-yl]-5-methyl-1H-pyrazol-3-olate
• CAS: 1585971-89-6
• 化学式: C₁₄H₁₃ClN₄O₄
• 分子量: 336.735
• InChiKey: JROGFIDIJQLNDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基-1-甲硫基-2-硝基乙烯胺 、 乙酰乙酸乙酯 、 5-氯代水杨醛 在 哌啶 、 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 0.75h， 以80%的产率得到4-(6-chloro-2-(methylamino)-3-nitro-4H-chromen-4-yl)-3-methyl-1H-pyrazol-5-ol
  参考文献：
  名称：

  An expedient four-component domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles and chromenopyrazoles via nitroketene-N,S-acetal chemistry under solvent-free condition

  摘要：

  Combinatorial library of pyranopyrazoles and chromenopyrazoles was regioselectively synthesized in excellent yield from ethylacetoacetate, hydrazinehydrate, substituted aldehyde/salicylaldehyde with nitroketene-N,S-acetal in the presence of piperidine under solvent-free condition (SFC) in an eco-benign manner. This novel strategy excludes tedious extraction, chromatographic separation and recrystallization processes. The final product could be obtained by simple filtration by the addition of ethanol to the reaction mixture. This domino protocol generates biologically significant heterocycles with the formation of C-C, C=C, C-N, C=N, C-O bonds and one stereo-centre in a single operation via condensation/Knoevenagel/Michael/annulation sequences. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.019

文献信息

• An expedient four-component domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles and chromenopyrazoles via nitroketene-N,S-acetal chemistry under solvent-free condition
  作者：Kamalraja Jayabal、Thirumalai Perumal Paramasivan

  DOI：10.1016/j.tetlet.2014.02.019

  日期：2014.3

  Combinatorial library of pyranopyrazoles and chromenopyrazoles was regioselectively synthesized in excellent yield from ethylacetoacetate, hydrazinehydrate, substituted aldehyde/salicylaldehyde with nitroketene-N,S-acetal in the presence of piperidine under solvent-free condition (SFC) in an eco-benign manner. This novel strategy excludes tedious extraction, chromatographic separation and recrystallization processes. The final product could be obtained by simple filtration by the addition of ethanol to the reaction mixture. This domino protocol generates biologically significant heterocycles with the formation of C-C, C=C, C-N, C=N, C-O bonds and one stereo-centre in a single operation via condensation/Knoevenagel/Michael/annulation sequences. (c) 2014 Elsevier Ltd. All rights reserved.