4-(4-methoxyphenyl)-thiapyrrolizidine-spiro[2.3′]oxindole-spiro[3.3″]-8″-nitro-1″H-quinolin-4(2″H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(4-methoxyphenyl)-thiapyrrolizidine-spiro[2.3′]oxindole-spiro[3.3″]-8″-nitro-1″H-quinolin-4(2″H)-one
• 化学式: C₂₈H₂₄N₄O₅S
• 分子量: 528.588
• InChiKey: LPLBQUGWKLNWBN-DBWGNYCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  8-硝基-2,3-二氢-4(1H)-喹啉酮 在 四氢吡咯 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.16h， 生成 4-(4-methoxyphenyl)-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

文献信息

• 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
  作者：Kumarasamy Chandraprakash、Mathan Sankaran、Chokalingam Uvarani、Ramasamy Shankar、Athar Ata、Frederic Dallemer、Palathurai Subramaniam Mohan

  DOI：10.1016/j.tetlet.2013.05.077

  日期：2013.7

  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.