8-chloro-3a,9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran-4-one

• 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: 8-chloro-3a,9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran-4-one
• 英文别名: ethyl (3aS,9aR)-5-chloro-9-oxo-3a,9a-dihydro-1H-cyclopenta[b]chromene-3-carboxylate
• 化学式: C₁₅H₁₃ClO₄
• 分子量: 292.719
• InChiKey: BITOEBDIGMDKFI-ZANVPECISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-丁二烯酸乙酯 、 8-Chloro-4-oxo-4H-chromene-3-carbaldehyde 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 80.0h， 以73%的产率得到8-chloro-3a,9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran-4-one
  参考文献：
  名称：

  Synthesis and evaluation of novel 3a,9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran-4-ones as antifungal agents

  摘要：

  An efficient synthesis of novel antifungal 3a, 9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran- 4-ones (10a-j) through 1,3-dipolar cycloaddition of all carbon 1,3-dipole (7) with substituted 3-formylchromones (8a-j) has been developed. The synthesized compounds were characterized spectro-scopically and evaluated in vitro for antifungal activity against various strains. Some of the compounds 10b, 10d and 10i exhibit significant inhibitory potential against Aspergillus niger, Saccahromyces cerevisiae and Candida albicans. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.086

文献信息

• Synthesis and evaluation of novel 3a,9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran-4-ones as antifungal agents
  作者：Richa Goel、Vishal Sharma、Abhishek Budhiraja、Mohan Paul S. Ishar

  DOI：10.1016/j.bmcl.2012.05.086

  日期：2012.7

  An efficient synthesis of novel antifungal 3a, 9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran- 4-ones (10a-j) through 1,3-dipolar cycloaddition of all carbon 1,3-dipole (7) with substituted 3-formylchromones (8a-j) has been developed. The synthesized compounds were characterized spectro-scopically and evaluated in vitro for antifungal activity against various strains. Some of the compounds 10b, 10d and 10i exhibit significant inhibitory potential against Aspergillus niger, Saccahromyces cerevisiae and Candida albicans. (C) 2012 Elsevier Ltd. All rights reserved.