N,2,5-trimethylaniline | 21354-48-3

• 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,2,5-trimethylaniline
• CAS: 21354-48-3
• 化学式: C₉H₁₃N
• mdl: MFCD11154311
• 分子量: 135.209
• InChiKey: FLLXIDNFXBLBMT-UHFFFAOYSA-N

物化性质

• 沸点：
  223.3±9.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P261,P273,P270,P271,P264,P280,P361+P364,P301+P310+P330,P302+P352+P312,P304+P340+P311,P403+P233,P405
• 危险品运输编号：
  2810
• 危险性描述：
  H301+H311+H331,H412

反应信息

• 作为反应物：
  描述：

  N,2,5-trimethylaniline 在 盐酸 、 正丁基锂 、 tetraphosphorus decasulfide 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 1,6-dimethyl-N-phenyl-2-sulfanylidene-3H-indole-3-carboxamide
  参考文献：
  名称：

  Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

  摘要：

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.

  DOI：

  10.1021/jm00039a016
• 作为产物：
  描述：

  N-(2,5-dimethylphenyl)methanimine 在 sodium tetrahydroborate 作用下， 反应 2.0h， 生成 N,2,5-trimethylaniline
  参考文献：
  名称：

  Stereospecific Copper-Catalyzed Domino Ring Opening and sp³ C–H Functionalization of Activated Aziridines with N-Alkylanilines

  摘要：

  Copper efficiently catalyzed nucleophilic ring opening, sp(3) C-H functionalization, and C-N bond formation in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines starting from N-sulfonylaziridines and N-alkylanilines. The products were obtained in high optical purities (95 -> 99% ee) with excellent functional group tolerance.

  DOI：

  10.1021/acs.orglett.6b03458

文献信息

• A Metal‐Free Direct Arene C−H Amination
  作者：Tao Wang、Marvin Hoffmann、Andreas Dreuw、Edina Hasagić、Chao Hu、Philipp M. Stein、Sina Witzel、Hongwei Shi、Yangyang Yang、Matthias Rudolph、Fabian Stuck、Frank Rominger、Marion Kerscher、Peter Comba、A. Stephen K. Hashmi

  DOI：10.1002/adsc.202100236

  日期：2021.6.8

  The synthesis of aryl amines via the formation of a C−N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C−H amination using hydroxylamine derivatives under benign

  通过形成 CN 键合成芳胺是制备功能材料、活性药物成分和生物活性产品的重要工具。通常，这种化学连接只能通过过渡金属催化的反应、光化学或电化学来实现。在这里，我们报告了在良性条件下使用羟胺衍生物进行的无金属芳烃 C-H 胺化。即使在存在各种官能团的情况下，胺化试剂 TsONHR 和芳烃底物之间的电荷转移相互作用也能实现芳烃的化学选择性胺化。氧气对于有效转化至关重要，其对电子转移步骤的加速作用已通过实验证明。此外，
• Improved and General Manganese‐Catalyzed N‐Methylation of Aromatic Amines Using Methanol
  作者：Jacob Neumann、Saravanakumar Elangovan、Anke Spannenberg、Kathrin Junge、Matthias Beller

  DOI：10.1002/chem.201605218

  日期：2017.4.24

  A novel lutidine‐based manganese PNP‐pincer complex has been synthesized for the selective N‐methylation of aromatic amines with methanol. Using borrowing hydrogen methodology, a selection of differently functionalized aniline derivatives is selectively methylated in good yields.

  已经合成了一种新型的基于二甲基吡啶的锰PNP钳配合物，用于甲醇对芳香胺的选择性N-甲基化。使用借用氢方法学，可以以良好的收率选择性地选择不同功能化的苯胺衍生物。
• Synthesis of New Sterically Hindered Anilines
  作者：Barry R. Steele、Spyros Georgakopoulos、Maria Micha-Screttas、Constantinos G. Screttas

  DOI：10.1002/ejoc.200700233

  日期：2007.7

  molecules containing sterically demandingalkyl groups feature in a number of important areas ofchemistry, such as homogeneous catalysis, materials chemis-try, medicinal chemistry, unsaturated and low-coordinationcompounds of the heavier main group elements. Of the vari-ous classes of aromatic compounds, the 2,6-dialkylanilinesfeature widely as starting materials for the synthesis ofSchiff bases, N-heterocyclic

  含有空间要求高的烷基的芳族分子在化学的许多重要领域具有特征，例如均相催化、材料化学、药物化学、较重主族元素的不饱和和低配位化合物。在各种芳香族化合物中，2,6-二烷基苯胺广泛用作合成席夫碱、N-杂环卡宾和金属配合物的相关配体的起始材料，特别是那些用于非均相催化的化合物。由于它们随时可用，除了苯胺
• [EN] OXACAZONE COMPOUNDS TO TREAT CLOSTRIDIUM DIFFICILE<br/>[FR] COMPOSÉS D'OXACAZONE POUR TRAITER CLOSTRIDIUM DIFFICILE
  申请人：BROAD INST INC

  公开号：WO2016019588A1

  公开（公告）日：2016-02-11

  Compounds, compositions, and methods for treating C. difficile are provided.

  提供用于治疗C. difficile的化合物、组合物和方法。
• [EN] INDANE DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS<br/>[FR] DÉRIVÉS D'INDANE ET LEUR UTILISATION COMME ACTIVATEURS DE LA GUANYLATE CYCLASE SOLUBLE
  申请人：NOVARTIS AG

  公开号：WO2017103888A1

  公开（公告）日：2017-06-22

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种化合物(I)或其药用可接受的盐；一种制造本发明化合物的方法，以及其治疗用途。本发明还提供了一种药理活性剂的组合和药物组合物。