4-methoxy-N-(4-nitrobenzyl)benzamide | 315248-36-3

• 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-methoxy-N-(4-nitrobenzyl)benzamide
• 英文别名: Benzamide, 4-methoxy-N-(4-nitrobenzyl)-；4-methoxy-N-[(4-nitrophenyl)methyl]benzamide
• CAS: 315248-36-3
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: CFVXVOXPSCJTKP-UHFFFAOYSA-N

物化性质

• 沸点：
  529.1±40.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(4-nitrobenzyl)benzamide 在 氯化亚砜 作用下， 生成 4-methoxy-N-(4-nitrobenzyl)benzimidoyl chloride
  参考文献：
  名称：

  Synthesis of Bis(2,4-diarylimidazol-5-yl) Diselenides from N-Benzylbenzimidoyl Isoselenocyanates

  摘要：

  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.

  DOI：

  10.1002/1522-2675(200204)85:4<1102::aid-hlca1102>3.0.co;2-t
• 作为产物：
  描述：

  4-碘苯甲醚 在 吡啶 、 N-甲基二环己基胺 、 sodium acetate 、 palladium diacetate 、 三乙胺 、 双(2-二苯基磷苯基)醚 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 44.0h， 生成 4-methoxy-N-(4-nitrobenzyl)benzamide
  参考文献：
  名称：

  Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications

  摘要：

  A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)(2) and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.

  DOI：

  10.1021/ol400138m

文献信息

• Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications
  作者：Mia N. Burhardt、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1021/ol400138m

  日期：2013.2.15

  A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)(2) and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.
• 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.