2-(4-chlorophenyl)-4H-indeno[2,1-d][1,3]oxazol-4-one | 1600516-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-4H-indeno[2,1-d][1,3]oxazol-4-one
• 英文别名: 2-(4-Chlorophenyl)indeno[2,1-d][1,3]oxazol-4-one；2-(4-chlorophenyl)indeno[2,1-d][1,3]oxazol-4-one
• CAS: 1600516-58-2
• 化学式: C₁₆H₈ClNO₂
• 分子量: 281.698
• InChiKey: RBZXNQAQIXRMDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-chlorobenzylidene)-2H-indene-1,3-dione 在 lead(IV) tetraacetate 、 potassium carbonate 、 富马酸二甲酯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 8.5h， 生成 2-(4-chlorophenyl)-4H-indeno[2,1-d][1,3]oxazol-4-one
  参考文献：
  名称：

  Synthesis and thermal transformations of spiro-fused N-phthalimidoaziridines

  摘要：

  Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3-diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiro[aziridine-2,2'-indene]-1',3'-diones in good yields. Heating these aziridines with standard dipolarophiles (N-phenylmaleimide, dimethyl acetylenedicarboxylate, maleate, and fumarate) leads, in most cases, to spiro[inden-2,2'-pyrrole] derivatives as products of 1,3-dipolar cycloaddition of the intermediate azomethine ylides with up to 70-95% yields in the case of N-phenylmaleimide. As is typical for 2-acylaziridines, the competing rearrangement into 2-aryl-4H-indeno[2,1-d][1,3]oxazol-4-ones prevails for less active dipolarophiles. Increasing the electron-releasing properties of the 3-aryl ring allows the observation of the push-pull effect of electron-donating and electron-withdrawing substituents on the ease of the three-membered ring-opening. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.014