N-(4-(trifluoromethyl)benzylidene)methanamine | 911101-44-5

• 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: N-(4-(trifluoromethyl)benzylidene)methanamine
• 英文别名: N-Methyl-4-(trifluoromethyl)benzenemethaneimine；N-methyl-1-[4-(trifluoromethyl)phenyl]methanimine
• CAS: 911101-44-5
• 化学式: C₉H₈F₃N
• 分子量: 187.164
• InChiKey: JPZBCJWUSOQAKL-UHFFFAOYSA-N

物化性质

• 沸点：
  194.8±40.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-(trifluoromethyl)benzylidene)methanamine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 N-甲基-4-三氟甲基苄胺
  参考文献：
  名称：

  Benzylamines: synthesis and evaluation of antimycobacterial properties

  摘要：

  The synthesis of benzylamines with various N-alkyl chains and substituents in the aromatic system as well as their evaluation on Mycobacterium tuberculosis H 37 Ra are described. The most active compounds in this test, N-methyl-3-chlorobenzylamine (19, MIC 10.2 micrograms/mL), N-methyl-3,5-dichlorobenzylamine (93, MIC 10.2 micrograms/mL), and N-butyl-3,5-difluorobenzylamine (103, MIC 6.4 micrograms/mL), also exhibited a marked inhibitory effect on Mycobacterium marinum and Mycobacterium lufu used for the determination of antileprotic properties. The combinations of 93 with aminosalicylic acid, streptomycin, or dapsone exert marked supra-additive effects on M. tuberculosis H 37 Ra.

  DOI：

  10.1021/jm00375a005
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 甲胺 反应 12.0h， 以100%的产率得到N-(4-(trifluoromethyl)benzylidene)methanamine
  参考文献：
  名称：

  通过亚胺基亚胺与亚胺酸酯的2 + 3环缩合有效合成与GFP发色团有关的新的4-Arylideneimidazolin-5-ones。

  摘要：

  由芳族醛和伯胺制得的各种席夫碱与2-（1-乙氧基乙叉基氨基）乙酸甲酯的2 + 3缩合反应可方便地获得广泛的取代的4-芳基亚氨基咪唑啉-5-酮类似物家族绿色荧光蛋白（GFP）生色团。 4-芳基亚胺达唑啉-5-酮-甲亚胺叶立德-席夫碱-杂环-2 + 3环加成

  DOI：

  10.1055/s-0029-1218796

文献信息

• Three-component carboarylation of unactivated imines with arynes and carbon nucleophiles
  作者：Jing-Kun Xu、Sheng-Jun Li、Hai-Yang Wang、Wen-Cong Xu、Shi-Kai Tian

  DOI：10.1039/c6cc09311f

  日期：——

  With 2-(trimethylsilyl)aryl triflates as aryne precursors, an unprecedented three-component carboarylation reaction of unactivated imines with arynes and carbon nucleophiles has been developed to access a variety of functionalized tertiary amines...

  以2-（三甲基甲硅烷基）芳基三氟甲磺酸酯为芳烃前体，已开发出前所未有的未活化亚胺与芳烃和碳亲核试剂的三组分碳芳基化反应，以获取各种官能化叔胺。
• Synthesis of α-Aminophosphonates via Phosphonylation of an Aryne–Imine Adduct
  作者：Taehyun Lim、Byeong Moon Kim

  DOI：10.1021/acs.joc.0c01410

  日期：2020.10.16

  Multicomponent phosphonylation is accomplished upon the reaction of an imine with an aryne generated in situ in the presence of a dialkyl phosphite. This transition-metal-free protocol shows a broad substrate scope, providing a variety of α-aminophosphonates in moderate to good yields. A plausible mechanism for the reaction is proposed based on a deuterium exchange experiment.

  在亚磷酸二烷基酯存在下，亚胺与原位生成的芳烃反应可完成多组分膦酰化反应。这种无过渡金属的方案显示了广泛的底物范围，可提供中等至良好产率的多种α-氨基膦酸酯。基于氘交换实验，提出了一种合理的反应机理。
• Diastereoselective One-Pot Synthesis of Tetrafunctionalized 2-Imidazolines
  作者：Guido V. Janssen、Paul Slobbe、Maurice Mooijman、Art Kruithof、Andreas W. Ehlers、Célia Fonseca Guerra、F. Matthias Bickelhaupt、J. Chris Slootweg、Eelco Ruijter、Koop Lammertsma、Romano V. A. Orru

  DOI：10.1021/jo500790n

  日期：2014.6.6

  tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity

  描述了四官能化的2-咪唑啉的方便的反式一锅合成。我们对这些有价值的杂环骨架的研究方法涉及在腈基乙腈或三氟甲磺酸腈和亚胺之间进行正式的1,3-偶极环加成反应。一项详细的实验研究与对反应路线的高级计算探索相结合，揭示了一条合理的反应路线，该路线解释了所观察到的非对映选择性。
• Unprecedented Ring-Ring Interconversion of N,P,C-Cage Ligands
  作者：José Manuel Villalba Franco、Gregor Schnakenburg、Arturo Espinosa Ferao、Rainer Streubel

  DOI：10.1002/chem.201405754

  日期：2015.2.23

  types of ligand N,P,C‐cage structures 5 and 6 were found to be in an unprecedented equilibrium, with 5 a,f as the predominant species. Transient electrophilic terminal phosphinidene complexes 10 a–f serve as intermediates in both ligand interconversions (5 a,f↔6 a,f), as evidenced through trapping reactions with phenylacetylene and N‐methyl‐C‐phenylcarbaldimine, thus leading to the novel N,P,C‐cage complexes

  新颖的N，P，C-笼配合物5 - ˚F和6 - ˚F已经由反应得到P -pentamethylcyclopentadienylphosphinidene复杂2，从2热产生ħ -azaphosphirene复杂1，与Ñ甲基Ç -芳基碳二胺3 a – f。Li / Cl膦基类固醇络合物8与3 a，b反应生成N，P，C笼式络合物6 a，b，而与3 c – f，仅以微不足道的量获得了配合物6c - f。发现两种类型的配体N，P，C笼结构5和6处于空前的平衡状态，其中5 a和f为主要物种。瞬态电子末端亚膦络合物10 - ˚F用作在这两个配位体的互变的中间体（5，˚F ↔ 6，˚F），通过捕获与苯乙炔和反应证明Ñ甲基Ç -phenylcarbaldimine，从而导致新的N- ，P，C笼络合物13b和15。DFT计算预测两种N，P，​​C笼型配体的相对能之间的微小差异，以及作为常见前体的氨基膦亚基配合
• One-Pot Transformation of Aldehydes to Ketones via Minisci-Type Reaction of Imines
  作者：Zakhar M. Rubanov、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1021/acs.orglett.3c03764

  日期：2023.12.8

  A method for the conversion of aldehydes to ketones via the preliminary formation of aldiminines is described. The imines are involved in acid promoted Minisci-type reaction with alkyl radicals generated from esters of N-hydroxylphthalimide under photoredox conditions. Aminyl radical cations formed after the addition of the iminium ions are believed to be key intermediates, which determine the reaction

  描述了一种通过初步形成醛亚胺将醛转化为酮的方法。亚胺参与酸促进的 Minisci 型反应，与在光氧化还原条件下由N-羟基邻苯二甲酰亚胺的酯产生的烷基自由基发生反应。添加亚胺离子后形成的氨基自由基阳离子被认为是决定反应结果的关键中间体。