methyl 4-(1-phthalimido-1',3'-dioxo-1',3'-dihydrospiro[aziridine-2,2'-inden]-3-yl)benzoate | 1600516-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 4-(1-phthalimido-1',3'-dioxo-1',3'-dihydrospiro[aziridine-2,2'-inden]-3-yl)benzoate
• 英文别名: Methyl 4-[1-(1,3-dioxoisoindol-2-yl)-1',3'-dioxospiro[aziridine-3,2'-indene]-2-yl]benzoate；methyl 4-[1-(1,3-dioxoisoindol-2-yl)-1',3'-dioxospiro[aziridine-3,2'-indene]-2-yl]benzoate
• CAS: 1600516-59-3
• 化学式: C₂₆H₁₆N₂O₆
• 分子量: 452.423
• InChiKey: HQURTSIMXLCBDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 methyl 4-(1-phthalimido-1',3'-dioxo-1',3'-dihydrospiro[aziridine-2,2'-inden]-3-yl)benzoate 以 苯 为溶剂， 反应 1.5h， 以71%的产率得到methyl rac-(3'R,3a'R,6a'S)-4-(1,3,4',6'-tetraoxo-5'-phenyl-2'-phthalimido-1,3,3',3a',4',5',6',6a'-octahydro-2'H-spiro[indene-2,1'-pyrrolo[3,4-c]pyrrol]-3'-yl)benzoate
  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：

  methyl 4-[(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)methyl]benzoate 、 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81%的产率得到methyl 4-(1-phthalimido-1',3'-dioxo-1',3'-dihydrospiro[aziridine-2,2'-inden]-3-yl)benzoate
  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 and thermal transformations of spiro-fused N-phthalimidoaziridines
  作者：Alena S. Pankova、Mikhail A. Kuznetsov

  DOI：10.1016/j.tetlet.2014.03.014

  日期：2014.4

  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.