trans-1-(Benzenesulfonyl)-2-benzoyl-3-phenylaziridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1-(Benzenesulfonyl)-2-benzoyl-3-phenylaziridine
• 英文别名: trans-2-benzoyl-1-benzenesulfonyl-3-phenylaziridine；[(2S,3R)-1-(benzenesulfonyl)-3-phenylaziridin-2-yl]-phenylmethanone
• 化学式: C₂₁H₁₇NO₃S
• 分子量: 363.437
• InChiKey: VYYHECSZIFMLKM-MFCMXAAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-1-(Benzenesulfonyl)-2-benzoyl-3-phenylaziridine 以 对二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以54%的产率得到2,5-二苯基恶唑
  参考文献：
  名称：

  Synthesis of oxazoles from α,β-unsaturated carbonyl compounds through 2-acylaziridines

  摘要：

  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.

  DOI：

  10.1134/s107042800908020x
• 作为产物：
  描述：

  chloramine-B 、 反式-查耳酮 在 tetramethylammonium tribromide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以14%的产率得到trans-1-(Benzenesulfonyl)-2-benzoyl-3-phenylaziridine
  参考文献：
  名称：

  Synthesis of oxazoles from α,β-unsaturated carbonyl compounds through 2-acylaziridines

  摘要：

  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.

  DOI：

  10.1134/s107042800908020x

文献信息

• 3-Substituted 2-Acyl-1-sulfonylaziridines from the Reaction of Triphenylbismuthonium 2-Oxoalkylides and N-Sulfonylaldimines. Reversal of the cis/trans-Isomer Ratios Depending on Base and Additive
  作者：Yoshihiro Matano、Masanori Yoshimune、Hitomi Suzuki

  DOI：10.1021/jo00119a056

  日期：1995.7
• 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.