(E)- 3-(thiophen-2-ylmethylene)-8-nitro-2,3-dihydroquinolin-4(1H)-one | 1446024-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: (E)- 3-(thiophen-2-ylmethylene)-8-nitro-2,3-dihydroquinolin-4(1H)-one
• 英文别名: (E)-3-(thiophen-2-ylmethylene)-8-nitro-2,3-dihydroquinolin-4(1H)-one
• CAS: 1446024-97-0
• 化学式: C₁₄H₁₀N₂O₃S
• 分子量: 286.311
• InChiKey: AOANMJOVMAMUGU-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.24
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)- 3-(thiophen-2-ylmethylene)-8-nitro-2,3-dihydroquinolin-4(1H)-one 、 靛红 、 噻莫西酸 以 甲醇 为溶剂， 反应 1.5h， 以89%的产率得到4-(thiophen-2‴-yl)thiapyrrolizidine-spiro[2.3′]oxindole-spiro[3.3″]-8″-nitro-1″H-quinolin-4(2″H)-one
  参考文献：
  名称：

  A strategic approach to the synthesis of novel class of dispiroheterocyclic derivatives through 1,3 dipolar cycloaddition of azomethine ylide with (E)-3-arylidene-2,3-dihydro-8-nitro-4-quinolone

  摘要：

  A series of novel dispiroheterocyclic system containing 4-quinolone nucleus are prepared by 1,3 dipolar cycloaddition of azomethine ylides with a newly prepared (E)-3-arylidene-2,3-dihydro-8-nitro-4-quinolone as dipolarophile. The ylide was generated in situ from isatin and sarcosine/1,3-thiazolane-4-carboxylic acid. The regio and stereochemistry of the synthesized product was established by H-1, C-13, 2D NMR techniques and single crystal X-ray analysis. The molecular mechanism of this cycloaddition has been investigated by means of the density functional theory (DFT) method. The experimental results of regioselectivity product of 1,3 dipolar cycloaddition have shown good agreement with the computed Frontier molecular orbital calculation (FMO) and fukui function analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.077
• 作为产物：
  描述：

  2-噻吩甲醛 、 8-硝基-2,3-二氢-4(1H)-喹啉酮 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以89%的产率得到(E)- 3-(thiophen-2-ylmethylene)-8-nitro-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  A strategic approach to the synthesis of novel class of dispiroheterocyclic derivatives through 1,3 dipolar cycloaddition of azomethine ylide with (E)-3-arylidene-2,3-dihydro-8-nitro-4-quinolone

  摘要：

  A series of novel dispiroheterocyclic system containing 4-quinolone nucleus are prepared by 1,3 dipolar cycloaddition of azomethine ylides with a newly prepared (E)-3-arylidene-2,3-dihydro-8-nitro-4-quinolone as dipolarophile. The ylide was generated in situ from isatin and sarcosine/1,3-thiazolane-4-carboxylic acid. The regio and stereochemistry of the synthesized product was established by H-1, C-13, 2D NMR techniques and single crystal X-ray analysis. The molecular mechanism of this cycloaddition has been investigated by means of the density functional theory (DFT) method. The experimental results of regioselectivity product of 1,3 dipolar cycloaddition have shown good agreement with the computed Frontier molecular orbital calculation (FMO) and fukui function analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.077