4-(tert-butyl)-N-(1-phenylethyl)aniline

• 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-(tert-butyl)-N-(1-phenylethyl)aniline
• 英文别名: 4-tert-butyl-N-(1-phenylethyl)aniline
• 化学式: C₁₈H₂₃N
• 分子量: 253.387
• InChiKey: NYACIZKNMJRBLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙烯 、 4-叔丁基苯胺 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 lithium tert-butoxide 、 S-1,1'-联-2-萘酚 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 48.17h， 以67%的产率得到4-(tert-butyl)-N-(1-phenylethyl)aniline
  参考文献：
  名称：

  可见光诱导的铜催化烯烃的分子间马氏化学加氢胺化

  摘要：

  已经建立了使用可商购的伯胺和仲胺的可见光诱导的铜催化的烯烃的分子间加氢胺化。这种有效的方法表现出对各种官能团的良好耐受性，并提供了以马尔可夫尼科夫区域选择性轻松接触一系列有价值的胺的方法。可以肯定地预期该方法将用于生物活性胺中，并且可能在发现铜催化的加氢官能​​化反应中提供新的潜力。

  DOI：

  10.1021/acs.orglett.9b02863

文献信息

• Comparative Study of the Catalytic Amination of Benzylic C–H Bonds Promoted by Ru(TPP)(py) ₂ and Ru(TPP)(CO)
  作者：Gabriele Manca、Carlo Mealli、Daniela Maria Carminati、Daniela Intrieri、Emma Gallo

  DOI：10.1002/ejic.201500656

  日期：2015.10

  the toluene substrate (PhCH3). Conversely, by staying on the singlet potential-energy surface, 6S can undergo dissociation of the pyridine ligand to form [Ru](NR). This complex can activate another RN3 molecule to form the bis-imido compound [Ru](NR)2, which is also catalytically active. At this point, the mechanism becomes independent of the nature of the original ligand L coordinated to [Ru].

  结合实验和基于 DFT 的理论分析阐明了轴向配体 L 对 Ru(卟啉)L 配合物在促进有机叠氮化物 (RN3) 对苄基 C-H 键的胺化方面的催化活性的影响。实验数据表明，Ru(TPP)(CO) (1) (TPP = 四苯基卟啉的二价阴离子) 的催化活性与 Ru(TPP)(py)2 (2) (py = 吡啶) 的催化活性相当。DFT 模型揭示了 2 可以被视为一种前催化剂，它在一个吡啶配体的吸能损失后变得活跃，得到不饱和物质 [Ru](py) (11) [Ru] = Ru(卟吩)}。该复合物将与 RN3 反应得到单亚胺单线态复合物 [Ru](py)(NR)S (6S)，它可以很容易地转化为在亚氨基 N 原子上具有双自由基特征的三线态异构体 6T。随后苄胺 PhCH2NHR 的形成是通过甲苯底物 (PhCH3) 的一个 C-H 键的自由基均裂活化而发生的。相反，通过停留在单线态势能表面，6S
• Iron-Catalyzed Oxidative Amination of Benzylic C(sp³)–H Bonds with Anilines
  作者：Yan-Ling Song、Bei Li、Zhen-Biao Xie、Dan Wang、Hong-Mei Sun

  DOI：10.1021/acs.joc.1c02311

  日期：2021.12.17

  Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of

  基于新型离子 Fe 中咪唑鎓阳离子上 N 取代基的简单变化，实现了苄基 C(sp 3 )-H 键与带有吸电子基团 (EWG) 或供电子基团 (EDG) 的苯胺的铁催化氧化胺化（三）配合物。咪唑鎓阳离子的结构改性导致氧化还原电位和铁金属中心催化性能的调节。使用DTBP作为氧化剂，[HI t Bu][FeBr 4 ]对带有EWG的苯胺表现出最高的催化活性，而[HIPym][FeBr 4 ]对EDG取代的苯胺更有效。这项工作为苄胺提供了替代途径，同时具有广泛的底物范围和铁催化的优点。
• Traceless Benzylic C−H Amination via Bifunctional <i>N</i> ‐Aminopyridinium Intermediates
  作者：Pritam Roychowdhury、Roberto G. Herrera、Hao Tan、David C. Powers

  DOI：10.1002/anie.202200665

  日期：2022.7.11

  C−H amination chemistry via traceless bifunctional nitrogen activation is reported. Sequential C−H aminopyridylation followed by Ni-catalyzed cross-coupling with aryl boronic acids affords the products of aryl nitrene insertion into C−H bonds. These products are unavailable by direct nitrene insertion due to the intrinsic instability of aryl nitrenes. The described method can be applied in the context

  据报道，通过无痕双功能氮活化进行 C−H 胺化化学。依次进行 CH 氨基吡啶化，然后进行镍催化与芳基硼酸的交叉偶联，得到芳基氮烯插入 CH 键的产物。由于芳基氮烯固有的不稳定性，这些产品无法通过直接氮烯插入获得。所描述的方法可以应用于药理学活性分子的背景下。
• Glycoporphyrin Catalysts for Efficient C–H Bond Aminations by Organic Azides
  作者：Giorgio Tseberlidis、Paolo Zardi、Alessandro Caselli、Damiano Cancogni、Matteo Fusari、Luigi Lay、Emma Gallo

  DOI：10.1021/acs.organomet.5b00436

  日期：2015.8.10

  We report herein the synthesis of new glycoporphyrin ligands which bear a glucopyranoside derivative on each meso-aryl moiety of the porphyrin skeleton. The saccharide unit is directly conjugated to the porphyrin or a triazole spacer is placed between the carbohydrate and porphyrin ring. The obtained glycoporphyrin ligands were employed to synthesize cobalt(II), ruthenium(II), and iron(III) complexes which were tested as catalysts of C-H bond aminations by organic azides. Two of the synthesized complexes were very efficient in promoting catalytic reactions, and the results achieved indicated that ruthenium and iron complexes show an interesting complementary catalytic activity in several amination reactions. The eco-friendly iron catalyst displayed very good chemical stability in catalyzing the amination reaction for three consecutive runs without losing catalytic activity.
• Development of nonproprietary phosphine ligands for the Pd-catalyzed amination reaction
  作者：Robert A. Singer、Michaël Doré、Janice E. Sieser、Martin A. Berliner

  DOI：10.1016/j.tetlet.2006.03.132

  日期：2006.5

  A new family of pyrazole and bi-pyrazole phosphine ligands are reported that perforin efficiently in the Pd-catalyzed amination reaction. Of the ligands screened, ligand 1 emerged as the most compatible for couplings involving both primary and secondary amines with typical yields of 84-99%. (c) 2006 Elsevier Ltd. All rights reserved.