1-methyl-2-(4-nitrobenzyl)benzene | 92199-60-5

• 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: 1-methyl-2-(4-nitrobenzyl)benzene
• 英文别名: 4-nitro-2'-methyldiphenylmethane；1-Methyl-2-[(4-nitrophenyl)methyl]benzene
• CAS: 92199-60-5
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: HPMJHVSKJYVFIF-UHFFFAOYSA-N

物化性质

• 沸点：
  180-183 °C(Press: 6.5 Torr)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(4-nitrobenzyl)benzene 在 溶剂黄146 、 锌 作用下， 反应 0.5h， 生成 4-[(2-Methylphenyl)methyl]aniline
  参考文献：
  名称：

  Quinolone Carboxylic Acids as a Novel Monoketo Acid Class of Human Immunodeficiency Virus Type 1 Integrase Inhibitors

  摘要：

  Human immunodeficiency virus type 1 (HIV-1) integrase is a crucial target for antiretroviral drugs, and several keto-enol acid class (often referred to as diketo acid class) inhibitors have clinically exhibited marked antiretroviral activity. Here, we show the synthesis and the detailed structure-activity relationship of the quinolone carboxylic acids as a novel monoketo acid class of integrase inhibitors. 6-(3-Chloro-2-fluorobenzyl)- 1-((2,S)-1-hydroxy-3,3-dimethylbutan-2-yl)-7-methoxy-4-oxo- 1,4-dihydroquinoline-3-carboxylic acid 51, which showed an IC50 of 5.8 nM in the strand transfer assay and an ED50 of 0.6 nM in the antiviral assay, and 6-(3-chloro-2-fluorobenzyl)-1-((2S)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-4-dihydroquinoline-3-carboxylic acid 49, which had an IC50 of 7.2 nM and an ED50 of 0.9 nM, were the most potent compounds in this class. The monoketo acid 49 was much more potent at inhibiting integrase-catalyzed strand transfer processes than 3'-processing reactions, as is the case with the keto-enol acids. Elvitegravir 49 was chosen as a candidate for further studies and is currently in phase 3 clinical trials.

  DOI：

  10.1021/jm900460z
• 作为产物：
  描述：

  4-叔丁基甲苯 生成 1-methyl-2-(4-nitrobenzyl)benzene
  参考文献：
  名称：

  BIANK, H. U.;SILBER, G.

  摘要：

  DOI：

文献信息

• Dual copper- and photoredox-catalysed C(sp²)–C(sp³) coupling
  作者：Euan B. McLean、Vincent Gauchot、Sebastian Brunen、David J. Burns、Ai-Lan Lee

  DOI：10.1039/c9cc01718f

  日期：——

  The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C–C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp2)–C(sp3) cross-couplings between aryl boronic acids and benzyl bromides.

  铜催化与可见光光氧化还原催化以合作方式的结合最近已成为开发新型C–C键形成反应的通用手段。在这项工作中，利用铜和光氧化还原双重催化作用来实现芳基硼酸和苄基溴之间的C（sp 2）–C（sp 3）交叉偶联。
• Superacid BF₃–H₂O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water
  作者：Shuting Zhang、Xiaohui Zhang、Xuege Ling、Chao He、Ruofeng Huang、Jing Pan、Jiaqiang Li、Yan Xiong

  DOI：10.1039/c4ra04059g

  日期：——

  An efficient in situ prepared superacid BF₃–H₂O promoted benzylation of arenes using benzyl alcohols and acetates achieves various diarylalkanes.

  一种高效的原位制备的超强酸BF3-H2O促进的芳烃苄基化反应，使用苄醇和醋酸酯制备各种二芳基烷烃。
• A Study of <i>N</i>-Nitrosoamide-Mediated Friedel−Crafts Type Benzylation of Benzene−Toluene and Benzene−Anisole¹^a
  作者：Ron W. Darbeau、Emil H. White

  DOI：10.1021/jo9916378

  日期：2000.2.1

  deuterium rearrangements (or coupled benzyl rearrangements) in the arenium ion intermediate. Kinetic isotope effects were not detected. The methyl substituent on toluene appears to affect intermolecular selectivity (k(T)/k(B)) and intramolecular selectivity (o, m, p distribution) to similar degrees. A mechanism is proposed in which both selectivities are determined by activation energy differences in

  氮分离的碳阳离子-羧酸根离子对被用作芳族化合物烷基化反应中碳阳离子的来源。N-亚硝基酰胺用于这些氮分子分离的离子对是研究烷基化的标准酸催化Friedel-Crafts方法的极佳替代品，因为它具有以下变量：亲电试剂的高反应活性，产物的稳定性，严格的动力学控制，均质性，没有过度烷基化，化学反应简单以及良好的产品平衡。在苯-甲苯和苯甲醚-苯混合物的脱氨苄基反应中，k（X）/ k（B）和％间位异构体的值与标准苄基化反应中观察到的值显着不同，这表明脱氨基亲电体比标准Friedel-Crafts方法生成的亲电性更高。反应显示分子间和分子内选择性之间成正比，因此遵循布朗选择性关系（BSR）。2,4,6-三甲苯基甲苯的苄基化未提供任何证据表明在芳族离子中间体中发生氘重排（或偶合的苄基重排）。未检测到动力学同位素效应。甲苯上的甲基取代基似乎以相似的程度影响分子间选择性（k（T）/ k（B））和分子内选择性（
• The Reactivity-Selectivity principle and the electrophilic substitution of aromatic compounds
  作者：Emil H. White

  DOI：10.1016/s0040-4039(97)10083-1

  日期：1997.11

  application of the Reactivity-Selectivity principle (RSP) to the Friedel-Crafts alkylation reaction has been reinvestigated using the N-nitrosoamide decomposition as the source of electrophiles. Plots of pfvsσ+ for 4-methylbenzyl, benzyl, 4-chlorobenzyl, and 4-nitrobenzyl cations] yielded ϱ values of −3.4, −2.5, −2.4, and −1.2, resp. The data indicate that the Reactivity-Selectivity Principle applicable

  已使用N-亚硝酰胺分解作为亲电试剂的来源，对反应选择性原则（RSP）在Friedel-Crafts烷基化反应中的应用进行了重新研究。对于4-甲基苄基，苄基，4-氯苄基和4-硝基苄基阳离子，p f与σ +的关系图得出yield值分别为-3.4，-2.5，-2.4和-1.2。数据表明适用于芳族化合物的亲电取代的反应性-选择性原理与文献中的要求相反。关于弗里德-克拉夫茨苄基反应应发生反应性逆转的说法也有争议。
• Friedel-Crafts Benzylation of Activated and Deactivated Arenes
  作者：Gabriel Schäfer、Jeffrey W. Bode

  DOI：10.1002/anie.201105380

  日期：2011.11.11

  going back makes possible facile Friedel–Crafts benzylations with moderate reaction temperatures, simple reaction workups, and improved substrate scope for the formation of synthetically important diarylmethanes (see scheme). Upon complexation with BF3⋅OEt2, hydroxamates serve as reversible leaving groups that stabilize highly reactive carbocations. Even deactivated arenes and electron‐deficient benzylhydroxamates

  NO的返回使温和的反应温度，简单的反应后处理和改进的形成重要合成二芳基甲烷的底物范围（参见方案）的Friedel-Crafts苄基化成为可能。在用BF络合3 ⋅OEt 2，异羟肟酸盐充当稳定高反应性的碳阳离子可逆的离去基团。在这些条件下，即使是失活的芳烃和缺电子的苄基异羟肟酸酯也可以干净地反应。