3,5-dimethyl-N-(1-phenylethyl)aniline | 906319-43-5

• 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: 3,5-dimethyl-N-(1-phenylethyl)aniline
• CAS: 906319-43-5
• 化学式: C₁₆H₁₉N
• mdl: MFCD11145885
• 分子量: 225.334
• InChiKey: HDVLWEGUELRBQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-N-(1-phenylethyl)aniline 在 正丁基锂 、 四氯化硅 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 16.0h， 生成 (3,5-Dimethyl-phenyl)-(1-phenyl-ethyl)-trichlorosilanyl-amine
  参考文献：
  名称：

  SYNTHESIS AND CHARACTERIZATION OF NEW (CHLOR0)AMINOSILANES: X-RAY CRYSTAL STRUCTURE OF [(2,6-Me₂C₆H₃NH)₂SiCl₂]

  摘要：

  Starting from racemic alpha -methylbenzyl amine or alpha -methylbenzyl bromide, new (amino)trichlorosilanes (MePhC(H))(SiMe3)NSiCl3(1) and (MePhC(H))(2,6-Me2C6H3) NSiCl3 (2) have been synthesized in good yields. The products have been characterized by analytical and IR, mass, and NMR (H-1 and Si-29) spectroscopic techniques. The diamino-dichlorosilane (2,6-Me2C6H3NH)(2)SiCl2 (3) obtained as the side product during the synthesis of 2 has been characterized by a single crystal X-ray diffraction study.

  DOI：

  10.1080/10426500108040247
• 作为产物：
  描述：

  N-(3,5-dimethylphenyl)-1-phenylethan-1-imine 在 [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]triethylphosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 、 二甲基苯基硅烷 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 3,5-dimethyl-N-(1-phenylethyl)aniline
  参考文献：
  名称：

  带有轴向手性硫醇盐配体的束缚Ru-S配合物，用于协同Si-H键活化：在对映选择性亚胺还原中的应用

  摘要：

  据报道有一个轴向手性的2,6-二甲磺基苯基与硫连接。它的多步制备从（S）-苯酚开始，巯基通过无消旋热纽曼-科沃特重排反应建立。用一个1，3，3，5-三氯叔丁基基团修饰的新的手性硫醇盐配体用于束缚氯化钌络合物的合成。它的光谱特征显示了钌中心的溶剂依赖性差向异构。主要的非对映异构体在晶体学上具有特征。用四[3,5-双（三氟甲基）苯基]硼酸酯（NaBAr F 4）提取氯化物可得到相应的配位不饱和钌配合物，并带有Ru-S键。在此Ru-S键上的Si-H键激活以同步方式进行时尚，但具有适度的面部选择性（dr = 70：30），生成非对映体手性钌钌氢化硅烷加合物。它们在催化亚胺氢化硅烷化中的应用导致了有希望的对映体诱导（40％ee），从而为涉及协同Si-H键活化的不对称催化提供了概念证明。

  DOI：

  10.1002/chem.201700304

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• A General Palladium-Phosphine Complex To Explore Aryl Tosylates in the N-Arylation of Amines: Scope and Limitations
  作者：Pui Ying Choy、Kin Ho Chung、Qingjing Yang、Chau Ming So、Raymond Wai-Yin Sun、Fuk Yee Kwong

  DOI：10.1002/asia.201800575

  日期：2018.9.4

  heterocycles such as indole, carbazole, pyrrole, 10‐phenothiazine, and 10‐phenoxazine were shown to be feasible coupling partners under this catalytic system. The described reaction conditions tolerate a wide range of functional groups and allow an array of aromatic amines as well as unsymmetrical amine products to be easily accessed from the various phenolic derivatives. Interestingly, this catalyst

  提出了使用芳基和杂芳基甲苯磺酸盐对各种胺进行单选择性N-芳基化反应的范围和局限性。空气稳定且易于接近的Pd（OAc）2 / CM-phos CM-phos = 2- [2-（二环己基膦基）苯基] -1-甲基-1 H-吲哚}催化剂体系能够处理各种芳基甲苯磺酸酯底物以及胺亲核试剂，包括伯和仲环状/无环脂族胺和苯胺。在这种催化体系下，含NH的杂环如吲哚，咔唑，吡咯，10-吩噻嗪和10-吩恶嗪被证明是可行的偶联伙伴。所描述的反应条件容许宽范围的官能团，并允许从各种酚衍生物容易地获得一系列的芳族胺以及不对称胺产物。有趣的是，该催化剂体系甚至提供了在水介质中进行反应的机会。我们还报道了旋光性α-中心手性胺与芳基甲苯磺酸盐的分子间偶联，而没有削弱对映体的纯度。
• Highly Selective Room-Temperature Copper-Catalyzed C−N Coupling Reactions
  作者：Alexandr Shafir、Stephen L. Buchwald

  DOI：10.1021/ja063063b

  日期：2006.7.1

  the copper-catalyzed coupling of aryl iodides with aliphatic amines occurs at room temperature in as little as 1 h. These high reaction rates allow for the coupling of a wide range of aryl and heteroaryl iodides at room temperature. This method is highly tolerant of a number of reactive functional groups, including -Br and aromatic -NH2 as well as phenolic and aliphatic -OH. The high selectivity of

  通过使用环状 β-二酮作为支持配体，芳基碘化物与脂肪胺的铜催化偶联在室温下仅需 1 小时即可发生。这些高反应速率允许在室温下偶联范围广泛的芳基和杂芳基碘化物。该方法对许多反应性官能团具有高度耐受性，包括 -Br 和芳香族 -NH2 以及酚类和脂肪族 -OH。CuI-β-二酮催化剂对脂肪胺的高选择性代表了对基于钯的方法的有用补充。
• Nickel-Catalyzed N-Alkylation of Acylhydrazines and Arylamines Using Alcohols and Enantioselective Examples
  作者：Peng Yang、Caili Zhang、Yu Ma、Caiyun Zhang、Aijie Li、Bo Tang、Jianrong Steve Zhou

  DOI：10.1002/anie.201708949

  日期：2017.11.13

  atom‐economic way to prepare alkylamines, ideally with water as the sole byproduct. Herein, nickel catalysts are used for direct N‐alkylation of hydrazides and arylamines using racemic alcohols. Moreover, a nickel catalyst of (S)‐binapine was used for an asymmetric N‐alkylation of benzohydrazide with racemic benzylic alcohols.

  胺和醇之间的借位氢反应是制备烷基胺的原子经济方法，理想情况下以水为唯一副产物。本文中，镍催化剂用于使用消旋醇直接对酰肼和芳基胺进行N-烷基化反应。此外，（S）-binapine的镍催化剂用于苯并肼与外消旋苯甲醇的不对称N-烷基化反应。
• In Water Markovnikov Hydration and One‐Pot Reductive Hydroamination of Terminal Alkynes under Ruthenium Nanoparticle Catalysis
  作者：Caterina Risi、Elena Cini、Elena Petricci、Simone Saponaro、Maurizio Taddei

  DOI：10.1002/ejic.201901235

  日期：2020.3.27

  catalyst. Introducing sodium formate in the aqueous phase and using a stoichiometric amount of amines, the Ru nanoparticle nanomicelle catalyst gave the first example of one‐pot single‐step hydroamination of alkynes with the formation of the corresponding secondary amines. The reaction is characterized by low environmental impact as TGPS‐750‐M is required in low amount, and organic solvents employed only

  在Shvo催化剂[2,3,4,5-四苯基-1,3-环戊二烯-1-醇，钌（II）配合物]存在下，少量苯胺和TGPS-750-M表面活性剂，末端炔烃在微波（MW）电介质加热下以水为溶剂水合，转化率高，收率高。与钌络合物通常观察到的反应不同，该反应仅产生马尔可夫尼科夫产物。在MWs的影响下，形成了嵌入纳米胶束环境的Ru纳米颗粒，作为有效的水合催化剂。在水相中引入甲酸钠并使用化学计量的胺，Ru纳米颗粒纳米胶束催化剂是炔烃单步单步加氢胺化并形成相应仲胺的第一个实例。