N,2,4-三甲基苯胺 | 13021-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,2,4-三甲基苯胺
• 英文名称: N,2,4-trimethylaniline
• 英文别名: N-Methyl-2,4-dimethyl-anilin；N,2,4-trimethylbenzenamine
• CAS: 13021-13-1
• 化学式: C₉H₁₃N
• mdl: MFCD10687533
• 分子量: 135.209
• InChiKey: ZIOFXYGGAJKWHX-UHFFFAOYSA-N

物化性质

• 熔点：
  250-252 °C
• 沸点：
  105-107 °C(Press: 15 Torr)
• 密度：
  0.955±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 保留指数：
  1951.2

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

• 危险等级：
  IRRITANT
• 海关编码：
  2921430090

反应信息

• 作为反应物：
  描述：

  N,2,4-三甲基苯胺 在 盐酸 、 正丁基锂 、 tetraphosphorus decasulfide 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 1,5-Dimethyl-2-indolinethione
  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-((1H-苯并[d] [1,2,3]三唑-1-基)甲基)-2,4-二甲基苯胺 在 sodium tetrahydroborate 作用下， 生成 N,2,4-三甲基苯胺
  参考文献：
  名称：

  Rewcastle, Gordon W.; Denny, William A., Heterocycles, 1994, vol. 37, # 2, p. 701 - 708

  摘要：

  DOI：

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，
• CO2 as a C1-building block for the catalytic methylation of amines
  作者：Olivier Jacquet、Xavier Frogneux、Christophe Das Neves Gomes、Thibault Cantat

  DOI：10.1039/c3sc22240c

  日期：——

  A novel catalytic reaction has been designed to utilize, for the first time, CO2 as a C1 feedstock in the synthesis of N-methylamines. Simple zinc catalysts, based on commercially available zinc salts and ligands, prove highly efficient in promoting both a 6 electron reduction of carbon dioxide and the formation of a C–N bond, using hydrosilanes and amines.

  设计了一种新型催化反应，首次利用二氧化碳作为C1原料，在N-甲基胺的合成中发挥了作用。基于商业可获得的锌盐和配体，简便的锌催化剂表现出高效的特点，能够促进二氧化碳的6电子还原以及使用氢硅烷和胺的C-N键的形成。
• 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
• Palladium-Catalyzed Aminocarbonylation of Aryl Iodides with Amides and<i>N</i>-alkyl Anilines
  作者：Longfei Ran、Zhi-Hui Ren、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1002/asia.201301245

  日期：2014.2

  A novel and efficient palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of a variety of valuable imides and tertiary benzanilides under an atmospheric pressure of CO.

  已经开发了新颖且有效的钯催化的酰胺基和N-烷基苯胺基的芳基碘化物的氨基羰基化反应。该反应可耐受多种官能团，是在CO的大气压下快速合成各种有价值的酰亚胺和叔苯甲酰叔胺的可靠方法。
• Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KOtBu promoted intramolecular C–H arylation
  作者：Sushila Sharma、Manoranjan Kumar、Shruti Sharma、Onkar S. Nayal、Neeraj Kumar、Bikram Singh、Upendra Sharma

  DOI：10.1039/c6ob01362g

  日期：——

  simple, efficient, rapid and transition metal-free methodology has been developed by utilizing vasicine (a natural product), as a catalyst for the synthesis of phenanthridinones and dihydrophenanthridines. The reaction proceeds through intramolecular C–H arylation with aryl halides in the presence of KOtBu as a base under microwave irradiation in sulfolane as a solvent. The reaction proceeds well with various

  已经开发了一种简单，有效，快速且无过渡金属的方法，该方法通过利用vasicine（天然产物）作为合成菲啶酮和二氢菲啶的催化剂。通过分子内C-H芳基化反应的进行，在KO的存在下芳基卤化物吨卜如在环丁砜微波辐射下碱作为溶剂。该反应在使用各种芳基碘，溴化物的情况下进行得很好，而在反应性较低的芳基氯化物下反应则更为显着，持续15分钟，从而以45-90％的收率提供了相应的产物。