4-methoxy-N-(phenyl(p-tolyl)methyl)aniline | 128854-12-6

• 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-methoxy-N-(phenyl(p-tolyl)methyl)aniline
• 英文别名: 4-methoxy-N-[(4-methylphenyl)-phenylmethyl]aniline
• CAS: 128854-12-6
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: GNRUFHYTDKNYFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-methoxy-N-(phenyl(p-tolyl)methylene)aniline 在 (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以90%的产率得到4-methoxy-N-(phenyl(p-tolyl)methyl)aniline
  参考文献：
  名称：

  分批和连续流动的二丙胺的光催化和化学选择性转移加氢

  摘要：

  描述了用于间歇和连续流动的亚胺化学选择性转移氢化的可见光光催化方法。该反应利用Et 3 N作为氢源和单电子供体，从而能够选择性还原衍生自含有其他可还原官能团（包括腈，卤化物，酯和酮）的二芳基酮亚胺的亚胺。Et 3 N的双重作用已通过荧光猝灭测量，瞬态吸收光谱和氘标记研究得到了证实。连续流处理有助于直接扩大反应规模。

  DOI：

  10.1021/acs.orglett.7b03565

文献信息

• Simple 1,2-Diamine Ligands for Asymmetric Addition of Aryllithium Reagents to Imines
  作者：Noemi Cabello、Jean-Claude Kizirian、Ségolène Gille、Alexandre Alexakis、Gérald Bernardinelli、Laurent Pinchard、Jean-Claude Caille

  DOI：10.1002/ejoc.200500447

  日期：2005.11

  Enantioselective addition of various aryllithium reagents to aromatic imines was catalyzed (20 mol-%) by readily accessible 1,2-diamines to afford a wide range of protected diarylmethylamines in up to 94 % enantiomeric excess. Furthermore, the absolute configuration of these arylation products was determined by using X-ray crystallography.

  各种芳基锂试剂与芳族亚胺的对映选择性加成反应 (20 mol-%) 由易于获得的 1,2-二胺催化，得到多种保护的二芳基甲基胺，对映体过量高达 94%。此外，这些芳基化产物的绝对构型是通过使用 X 射线晶体学确定的。
• Amine Functionalization through Sequential Quinone-Catalyzed Oxidation/Nucleophilic Addition
  作者：Martin A. Leon、Xinyun Liu、Johnny H. Phan、Michael D. Clift

  DOI：10.1002/ejoc.201600786

  日期：2016.9

  method for the synthesis of α-branched amines through formal oxidative C–H functionalization is reported. A commercially available quinone organocatalyst is employed to promote the aerobic oxidation of primary amines to the corresponding N-protected imines, which are then trapped in situ with an appropriate nucleophile to give access to versatile functionalized amines in good to excellent yields (70–90 %)

  报道了一种通过形式氧化 C-H 功能化合成 α-支化胺的简单有效的方法。使用市售的醌有机催化剂来促进伯胺有氧氧化成相应的 N 保护亚胺，然后用适当的亲核试剂原位捕获这些亚胺，从而以良好至极好的收率（70-90%）获得多功能功能化胺）。
• Enantioselective addition of aryllithium reagents to aromatic imines mediated by 1,2-diamine ligands
  作者：Noemi Cabello、Jean-Claude Kizirian、Alexandre Alexakis

  DOI：10.1016/j.tetlet.2004.04.100

  日期：2004.6

  A variety of optically enriched amines have been obtained by addition of aryllithium reagents to aromatic imines using N,N′-tetramethylcyclohexane-1,2-diamine as chiral ligands. Enantiomeric excesses up to 90% could be obtained.

  通过使用N，N′-四甲基环己烷-1，2-二胺作为手性配体将芳基锂试剂加到芳族亚胺上，已经获得了各种光学富集的胺。可获得高达90％的对映体过量。
• Synthesis of Benzhydryl-Substituted Amines by Silanolate-Mediated Aldimine Arylation with Functionalized Aryl Nucleophiles Released from Diazene-Based Reagents
  作者：Aliyaah J. M. Rahman、Lucie Finck、Wolfgang Obermayer、Martin Oestreich

  DOI：10.1021/acs.orglett.2c03798

  日期：2022.12.16

  imine derivatives with functionalized aryl pronucleophiles is reported. The aryl nucleophiles are released from silicon-protected aryl-substituted diazenes by desilylation with potassium trimethylsilanolate concomitant with the loss of dinitrogen. A broad range of functional groups is tolerated in the aryl nucleophile but, depending upon their electronic effect, require specific groups at the imine

  报道了一种无过渡金属的方案，用于N -苯基 - 和N -苯甲酰基取代的苯甲醛衍生亚胺衍生物与功能化芳基亲核试剂的芳基化。芳基亲核试剂通过用三甲基硅烷醇钾进行脱甲硅烷基化并伴随二氮的损失从硅保护的芳基取代的二氮烯中释放出来。芳基亲核试剂可容许多种官能团，但根据它们的电子效应，亚胺氮原子上需要特定的基团。
• 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).