N-(o-bromobenzyl)succinimide | 115363-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(o-bromobenzyl)succinimide
• 英文别名: 1-(2-bromobenzyl)pyrrolidine-2,5-dione；1-[(2-Bromophenyl)methyl]pyrrolidine-2,5-dione
• CAS: 115363-86-5
• 化学式: C₁₁H₁₀BrNO₂
• mdl: MFCD14644606
• 分子量: 268.11
• InChiKey: FSJAXGIWDVVRPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  446.0±28.0 °C(Predicted)
• 密度：
  1.602±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(o-bromobenzyl)succinimide 在 bismuth(lll) trifluoromethanesulfonate 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 N-2-bromobenzyl-5-allylpyrrolidin-2-one
  参考文献：
  名称：

  Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst

  摘要：

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).

  DOI：

  10.1021/jo062077x
• 作为产物：
  描述：

  丁二酸酐 、 邻溴苄胺 在 4-二甲氨基吡啶 、 溶剂黄146 作用下， 反应 24.0h， 以61%的产率得到N-(o-bromobenzyl)succinimide
  参考文献：
  名称：

  Design and Optimization of Tricyclic Phtalimide Analogues as Novel Inhibitors of HIV-1 Integrase

  摘要：

  Human immunodeficiency virus type-1 integrase is an essential enzyme for effective viral replication and hence a valid target for the design of inhibitors. We report here on the design and synthesis of a novel series of phthalimide analogues as integrase inhibitors. The short synthetic pathway enabled us to synthesize a series of analogues with a defined structure diversity. The presence of a single carbonyl-hydroxy-aromatic nitrogen motif was shown to be essential for the enzymatic activity and this was confirmed by molecular docking studies. The enzymatically most active compound from this series is 743,4-dichlorobenzyl)-5,9dihydroxypyrrolo[3,4-g]quinoxaline-6,8-dione (151) with an IC50 value of 112 nM on the HIV-1 integrase enzyme, while ((7-(4-chlorobenzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoxaline-6,8-dione (15k)) showed an EC50 of 270 nM against HIV-1 in a cell-based assay.

  DOI：

  10.1021/jm049559q

文献信息

• Formation of fused tricyclic azetidinones and pyrrolidinones by intramolecular SH2 processes
  作者：A. L. J. Beckwith、D. R. Boate

  DOI：10.1021/jo00253a028

  日期：1988.9
• BECKWITH, A. L. J.;BOATE, D. R., J. ORG. CHEM., 53,(1988) N 18, C. 4339-4348
  作者：BECKWITH, A. L. J.、BOATE, D. R.

  DOI：——

  日期：——
• Design and Optimization of Tricyclic Phtalimide Analogues as Novel Inhibitors of HIV-1 Integrase
  作者：Wim G. Verschueren、Inge Dierynck、Katie I. E. Amssoms、Lili Hu、Paul M. J. G. Boonants、Geert M. E. Pille、Frits F. D. Daeyaert、Kurt Hertogs、Dominique L. N. G. Surleraux、Piet B. T. P. Wigerinck

  DOI：10.1021/jm049559q

  日期：2005.3.1

  Human immunodeficiency virus type-1 integrase is an essential enzyme for effective viral replication and hence a valid target for the design of inhibitors. We report here on the design and synthesis of a novel series of phthalimide analogues as integrase inhibitors. The short synthetic pathway enabled us to synthesize a series of analogues with a defined structure diversity. The presence of a single carbonyl-hydroxy-aromatic nitrogen motif was shown to be essential for the enzymatic activity and this was confirmed by molecular docking studies. The enzymatically most active compound from this series is 743,4-dichlorobenzyl)-5,9dihydroxypyrrolo[3,4-g]quinoxaline-6,8-dione (151) with an IC50 value of 112 nM on the HIV-1 integrase enzyme, while ((7-(4-chlorobenzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoxaline-6,8-dione (15k)) showed an EC50 of 270 nM against HIV-1 in a cell-based assay.
• Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst
  作者：Frédéric Pin、Sébastien Comesse、Bernard Garrigues、Štefan Marchalín、Adam Daïch

  DOI：10.1021/jo062077x

  日期：2007.2.1

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).