3-(4-chlorophenyl)-1-phthalimidospiro[aziridine-2,2’-indene]-1’,3’-dione | 1207272-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3-(4-chlorophenyl)-1-phthalimidospiro[aziridine-2,2’-indene]-1’,3’-dione
• 英文别名: 1-phthalimido-3-(4-chlorophenyl)spiro[aziridine-2,2'-indene]-1',3'-dione；1-Phthalimido-3-(4-chlorophenyl)spiro[aziridine-2,2'-indene]-1',3'-dione；3-(4-chlorophenyl)-1-(1,3-dioxoisoindol-2-yl)spiro[aziridine-2,2'-indene]-1',3'-dione
• CAS: 1207272-25-0
• 化学式: C₂₄H₁₃ClN₂O₄
• 分子量: 428.831
• InChiKey: OWLIAEKYPFHQER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-1-phthalimidospiro[aziridine-2,2’-indene]-1’,3’-dione 在 富马酸二甲酯 作用下， 以 苯 为溶剂， 反应 8.0h， 以37%的产率得到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
• 作为产物：
  描述：

  2-(4-chlorobenzylidene)-2H-indene-1,3-dione 、 氨基邻苯二甲胺 在 lead(IV) tetraacetate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以78%的产率得到3-(4-chlorophenyl)-1-phthalimidospiro[aziridine-2,2’-indene]-1’,3’-dione
  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

文献信息

• Synthesis of oxazoles from α,β-unsaturated carbonyl compounds through 2-acylaziridines
  作者：E. V. Beletskii、M. A. Kuznetsov

  DOI：10.1134/s107042800908020x

  日期：2009.8

  Oxidative addition of N-aminophthalimide to benzylideneacetone and chalcones followed by thermolysis of the arising 2-aryl-3-acyl-1-phthalimidoaziridines led to the formation of 2,5-disubstituted oxazoles in an overall yield 30-55%. Electron-donor substituents in the aryl fragment of 2-aryl-3-aroyl-1-phthalimidoaziridines accelerate their conversion into oxazoles, and similar substituents in the aroyl fragment retard this process. The possibility was demonstrated of going over to oxazoles from alpha,beta-unsaturated carbonyl compounds via 2-acyl-1-sulfonylaziridines employing chloramine-B. However ethyl 2 cyanocinnamate reacted with chloramine-B with the rupture of the C=C bond and the formation of N-benzylidene-benzenesulfamide.