N-benzyl-1-(4-(trifluoromethyl)phenyl)methanamine | 79128-85-1

• 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-benzyl-1-(4-(trifluoromethyl)phenyl)methanamine
• 英文别名: N-Benzyl-4-(trifluoromethyl)benzenemethaneamine；1-phenyl-N-[[4-(trifluoromethyl)phenyl]methyl]methanamine
• CAS: 79128-85-1
• 化学式: C₁₅H₁₄F₃N
• mdl: MFCD01475294
• 分子量: 265.278
• InChiKey: YVSUABKVWCZDNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  315.5±37.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-(4-(trifluoromethyl)phenyl)methanamine 在 sodium hydroxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 25.0~300.0 ℃ 、1.33 Pa 条件下， 反应 0.5h， 生成 1--4-butyl-3-(ethoxycarbonyl)-1,4-diazatricyclo<3.2.4.0^3,11.0^6,11>dodeca-7,9-dien-2-one
  参考文献：
  名称：

  Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles

  摘要：

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.

  DOI：

  10.1021/jo00052a015
• 作为产物：
  描述：

  N-benzylidene-4-trifluoromethylbenzylamine 在 sodium tetrahydroborate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以99%的产率得到N-benzyl-1-(4-(trifluoromethyl)phenyl)methanamine
  参考文献：
  名称：

  介孔钴/锰氧化物：用于胺-亚胺转化的高选择性双功能催化剂

  摘要：

  在本文中，我们讨论了使用钴掺杂的中孔氧化锰进行胺-醇交叉偶联以选择性产生对称或不对称亚胺的非均相催化方案。对该材料的表面化学和物理性质进行了深入研究，发现其出色的氧化还原性质和反应机理得到了密度密度理论（DFT）的量子力学计算的支持。

  DOI：

  10.1039/c8gc00862k

文献信息

• Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines
  作者：Pengqing Ye、Yinlin Shao、Xuanzeng Ye、Fangjun Zhang、Renhao Li、Jiani Sun、Beihang Xu、Jiuxi Chen

  DOI：10.1021/acs.orglett.9b04606

  日期：2020.2.21

  Homoleptic lanthanide complex Y[N(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed

  均一的镧系元素络合物Y [N（TMS）2] 3是一种高效的均相催化剂，可用于将硼化的仲酰胺和叔酰胺还原为相应的胺。发现一系列含有不同官能团如氰基，硝基和乙烯基的酰胺具有良好的耐受性。该转化也已经很好地应用于吲哚和吡哌贝地的合成。详细的同位素标记实验，对照实验和动力学研究为阐明反应机理提供了累积的证据。
• Efficient photocatalytic one-pot hydrogenation and N-alkylation of nitrobenzenes/benzonitriles with alcohols over Pd/MOFs: Effect of the crystal morphology &amp; “quasi-MOF” structure
  作者：Hongmei Cheng、Xingyu Long、Fengxia Bian、Chaofen Yang、Xingyan Liu、Heyan Jiang

  DOI：10.1016/j.jcat.2020.05.033

  日期：2020.9

  photocatalysts for highly efficient one-pot hydrogenation and N-alkylation of nitrobenzenes or benzonitriles with alcohols after in situ Pd photoreduction. Photocatalytic performance was evidently affected by the Fe-MOFs crystal size, morphology, crystalline structure alteration and “quasi-MOF” construction. One-pot hydrogenation and N-alkylation of benzonitriles with alcohols was achieved with excellent

  在可见光诱导的催化作用下的一锅多步反应具有可持续的绿色过程。在这里，配体结构的变化和2-MI协调的调制被用来调整Fe-MOFs的晶体尺寸，形态和晶体结构。Pd负载采用双溶剂浸渍。在N 2下煅烧形成具有保留形态的“准MOF”材料。上述改性材料被用作多功能光催化剂，用于原位Pd光还原后，硝基苯或苄腈与醇的高效一锅式加氢和N-烷基化。Fe-MOFs的晶体大小，形态，晶体结构改变和“准MOF”结构明显影响了光催化性能。首先在异相催化中以优异的催化性能实现了苯甲腈与醇的一锅式加氢和N-烷基化反应。在原位DRIFTS的协助下，提出了反应机理。
• Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions
  作者：Hao Song、Yao Xiao、Zhuohua Zhang、Wanjin Xiong、Ren Wang、Liangcheng Guo、Taigang Zhou

  DOI：10.1021/acs.joc.1c02413

  日期：2022.1.7

  efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine–BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to

  报道了一种简单而有效的铜催化腈选择性转移氢化为伯胺-硼烷和仲胺与恶氮硼烷-BH 3 配合物的方法。通过切换溶剂和铜催化剂在温和条件下实现选择性控制。通过该策略以高选择性和高达 95% 的产率合成了 30 多种伯胺-硼烷和 40 种仲胺。该策略应用于以89% 的收率合成15 N 标记。
• Oxidation of Amines and Sulfides Catalyzed by an Assembled Complex of Phosphotungstate and Non-Cross-Linked Amphiphilic Polymer
  作者：Shiro Ikegami、Yoichi M. Yamada、Hidetsugu Tabata、Hideyo Takahashi

  DOI：10.1055/s-2002-35596

  日期：——

  Oxidation of sulfides and amines was performed with an assembled catalyst of phosphotungstate and non-cross-linked amphiphilic polymer. The reactions proceeded with hydrogen peroxide under organic solvent-free conditions. This insoluble catalyst was reused five times with the turnover number up to 500.

  使用磷钨酸和非交联两性聚合物组装的催化剂进行了硫化物和胺的氧化反应。这些反应在无有机溶剂的条件下，以过氧化氢为氧化剂进行。这种不溶性催化剂可重复使用五次，其周转次数高达500次。
• Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines
  作者：Veronica Papa、Jose R. Cabrero-Antonino、Anke Spannenberg、Kathrin Junge、Matthias Beller

  DOI：10.1039/d0cy01078b

  日期：——

  hydrogenation of amides to amines is presented. The optimal catalytic system based on a combination of [Co(NTf2)2] and (p-anisyl)triphos (L3) in the presence of [Me3SiOTf] as acidic co-catalyst facilitates the direct hydrogenation of a broad range of amides to the corresponding amines under mild conditions. A set of control experiments indicate that, after the initial reduction of the amide carboxylic

  介绍了酰胺的第一个常规且有效的钴催化脱氧加氢为胺。在[Me 3 SiOTf]作为酸性助催化剂的情况下，基于[Co（NTf 2）2 ]和（对-茴香基）三磷（L3）的组合的最佳催化体系有利于广泛范围内的直接氢化。酰胺在温和的条件下转化为相应的胺。一组对照实验表明，在酰胺羧基最初还原为众所周知的半胱氨酸中间体后，反应主要通过C–O键断裂进行，尽管其他途径可能也有少量参与。