4-bromo-N-(4-nitrobenzyl)benzamide | 464934-83-6

• 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: 4-bromo-N-(4-nitrobenzyl)benzamide
• 英文别名: 4-bromo-N-[(4-nitrophenyl)methyl]benzamide
• CAS: 464934-83-6
• 化学式: C₁₄H₁₁BrN₂O₃
• 分子量: 335.157
• InChiKey: YPBKEXXXBKYQMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-N-(4-nitrobenzyl)benzamide 在 盐酸 、 tin 作用下， 生成 N-(4'-bromobenzoyl)-4-hydroxybenzylamine
  参考文献：
  名称：

  过氧化钾使苄基酰胺芳香羟基化

  摘要：

  在18冠6醚存在下，N-苄基酰胺与超氧化钾在苯中反应，生成邻羟基和对羟基羟基化产物。提出了该反应的机理，涉及超氧阴离子对酰胺羰基的亲核攻击和底物-超氧化物加合物从苄基亚甲基夺氢。

  DOI：

  10.1016/s0040-4020(01)97990-6
• 作为产物：
  描述：

  N-苄基-4-溴苯甲酰胺 生成 4-bromo-N-(4-nitrobenzyl)benzamide
  参考文献：
  名称：

  过氧化钾使苄基酰胺芳香羟基化

  摘要：

  在18冠6醚存在下，N-苄基酰胺与超氧化钾在苯中反应，生成邻羟基和对羟基羟基化产物。提出了该反应的机理，涉及超氧阴离子对酰胺羰基的亲核攻击和底物-超氧化物加合物从苄基亚甲基夺氢。

  DOI：

  10.1016/s0040-4020(01)97990-6

文献信息

• Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid
  作者：Mukund P. Sibi、Takahiro Soeta、Craig P. Jasperse

  DOI：10.1021/ol9018584

  日期：2009.12.3

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.
• Synthesis of Bis(2,4-diarylimidazol-5-yl) Diselenides from N-Benzylbenzimidoyl Isoselenocyanates
  作者：Plamen K. Atanassov、Yuehui Zhou、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/1522-2675(200204)85:4<1102::aid-hlca1102>3.0.co;2-t

  日期：2002.4

  The reaction of N-benzylbenzamides 6 with SOCl2 under reflux gave the corresponding N-benzylbenzimidoyl chlorides 7. Further treatment with KSeCN in dry acetone yielded imidoyl isosclenocyanates 3 (Scheme 2). These compounds, obtained in satisfying yields, proved to be stable enough to be purified and analyzed. Reaction of 3 with morpholine in dry acetone led to the corresponding selonourea derivatives 8. On treatment with Et3N, the 4-nitrobenzyl derivatives of type 3 were transformed into bis(2,4-diarylimidazol-5-yl) diselenides 9 (Scheme 3). This transformation takes place only when the benzyl residue bears an NO2 group and the phenyl group is not substituted with a strong electron-donating group. A reaction mechanism for the formation of 9 is proposed in Scheme 4. The key structures have been established by X-ray crystallography.
• Aromatic hydroxylation of benzylamides by potassium superoxide
  作者：Guido Galliani、Bruno Rindone

  DOI：10.1016/s0040-4020(01)97990-6

  日期：1981.1

  N-benzylamides react with potassium superoxide in benzene in presence of 18-crown-6 ether to give ortho and para hydroxylated products. A mechanism is proposed for this reaction, involving the nucleophilic attack of superoxide anion to amide carbonyl and hydrogen abstraction from benzyle methylene by the substrate-superoxide adduct.

  在18冠6醚存在下，N-苄基酰胺与超氧化钾在苯中反应，生成邻羟基和对羟基羟基化产物。提出了该反应的机理，涉及超氧阴离子对酰胺羰基的亲核攻击和底物-超氧化物加合物从苄基亚甲基夺氢。