N-(3-nitrophenyl)-1,1-diphenylmethylamine

• 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-(3-nitrophenyl)-1,1-diphenylmethylamine
• 英文别名: N-benzhydryl-3-nitroaniline
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: VMOBHDVDYIUJAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯甲醇 、 间硝基苯胺 在 sodium tetrachloroaurate(III) dihyrate 、 sodium 3-(diphenylphosphanyl)benzenesulfonate 作用下， 以 水 为溶剂， 反应 16.0h， 以75%的产率得到N-(3-nitrophenyl)-1,1-diphenylmethylamine
  参考文献：
  名称：

  金（III）/二苯基膦基-3-磺酸钠（TPPMS）催化水中缺电子苯胺的脱水N-苄基化

  摘要：

  抽象的 已经开发出一种用于缺电子的苯胺在水中的脱水N-苄基化的策略。金（III）/二苯基膦基苯-3-磺酸钠（TPPMS）催化剂作为路易斯酸非常有效，可活化醇并耐受有氧条件。Hammett在对位取代的苯甲醇的反应中的研究显示出负σ值，表明在速率确定sp 3 C–O键断裂步骤期间阳离子电荷的积累。逆动力学溶剂同位素效应（KSIE = 0.6）与特定的酸催化机理一致。这种简单的方案可以在原子经济过程中的温和条件下进行，而无需碱或其他添加剂，从而提供了电子不足的N-苄基苯胺具有中等至优异的收率，并且水是唯一的副产物。 已经开发出一种用于缺电子的苯胺在水中的脱水N-苄基化的策略。金（III）/二苯基膦基苯-3-磺酸钠（TPPMS）催化剂作为路易斯酸非常有效，可活化醇并耐受有氧条件。Hammett在对位取代的苯甲醇的反应中的研究显示出负σ值，表明在速率确定sp 3 C–O键断裂步骤期间阳离子电荷的积累。逆动力学溶剂同位素效应（KSIE

  DOI：

  10.1055/s-0037-1611519

文献信息

• Kinetics and Mechanism of Reactions of Benzhydryl Chlorides with Anilines
  作者：Saemin Chang、Han Joong Koh、Bon-Su Lee、Ikchoon Lee

  DOI：10.1021/jo00129a016

  日期：1995.12

  Nucleophilic substitution reactions of substituted benzhydryl chlorides with anilines in acetonitrile and methanol are investigated. The reactions are found to proceed by the attack of nucleophile on the preformed carbocation, I, within the ion pair. The cross-interaction constants, rho(XY), are relatively large in both acetonitrile (rho(X)Y = -2.47) and methanol (rho(XY) = -1.46). The isokinetic points (sigma(Y)(+)) where rho(X) (rho(nuc)) is zero and the sign of rho(X) changes, are observed at positive substrate substituent constants, sigma(Y)(+) = 0.13 and 0.22 in acetonitrile and methanol, respectively. The isokinetic phenomenon (rho(X) = 0) has been shown to occur when the thermodynamic driving force, Delta G degrees, is practically completely compensated for by the intrinsic barrier, Delta G(0)(double dagger). The two change in a compensatory manner; the intrinsic barrier becomes higher when resonance electron delocalization of the Y substituent to C-alpha is stronger, which in turn results when the thermodynamic driving force becomes higher by stronger electron-withdrawing alpha-substituents, R(1) and/or R(2).
• A Mild, One-Pot Synthesis of Arylamines<i>via</i>Palladium- Catalyzed Addition of Aryl Aldehydes with Amines and Arylboronic Acids in Water
  作者：Ajuan Yu、Yangjie Wu、Baoli Cheng、Kun Wei、Jingya Li

  DOI：10.1002/adsc.200800680

  日期：2009.3

  Abstractmagnified imageA mild, one‐pot synthesis of diarylmethylamines via the palladium‐catalyzed addition of aryl aldehydes with amines and arylboronic acids is reported. Best results were obtained in neat water with ammonium chloride as additive, affording diarylmethylamine derivatives as the main products.