2-methoxy-N-(3-tolyl)aniline | 137445-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methoxy-N-(3-tolyl)aniline
• 英文别名: 2-methoxy-N-(m-tolyl)aniline；2-methoxy-N-m-tolylaniline；N-(m-tolyl)-o-anisidine；2-methoxy-N-(3-methylphenyl)aniline
• CAS: 137445-06-8
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: CZYLPWMXDCRGFC-UHFFFAOYSA-N

物化性质

• 沸点：
  329.1±25.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-N-(3-tolyl)aniline 在 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以72%的产率得到1-methoxy-7-methyl-9H-carbazole
  参考文献：
  名称：

  Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

  摘要：

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

  DOI：

  10.1055/s-0032-1317175
• 作为产物：
  描述：

  3-甲基苯胺 在 palladium diacetate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 38.0h， 生成 2-methoxy-N-(3-tolyl)aniline
  参考文献：
  名称：

  Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

  摘要：

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

  DOI：

  10.1055/s-0032-1317175

文献信息

• Application of a 2-aryl indenylphosphine ligand in the Buchwald–Hartwig cross-coupling reactions of aryl and heteroaryl chlorides under the solvent-free and aqueous conditions
  作者：Yan Liu、Jia Yuan、Zi-Fei Wang、Si-Hao Zeng、Meng-Yue Gao、Mei-Lin Ruan、Jian Chen、Guang-Ao Yu

  DOI：10.1039/c7ob01199g

  日期：——

  An efficient solvent-free protocol for the Buchwald–Hartwig cross-coupling reaction of aryl and heteroaryl chlorides with primary and secondary amines using the Pd(dba)2/ligand 1 catalytic system has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.

  使用Pd（dba）2 /配体1催化系统开发了一种有效的无溶剂方案，用于芳基和杂芳基氯化物与伯胺和仲胺的布赫瓦尔德-哈特维格交叉偶联反应。值得注意的是，催化体系还可以在水性条件下有效地催化反应。
• Unexpected multicomponent reaction of 2/4-methoxyarylaldehydes with arylhydroxylamines and maleic anhydride: a novel synthesis of unsymmetrical diarylamines
  作者：V. Sridharan、K. Karthikeyan、S. Muthusubramanian

  DOI：10.1016/j.tetlet.2006.04.043

  日期：2006.6

  Unsymmetrical diarylamines have been synthesized by a novel, unexpected multicomponent reaction between methoxyarylaldehydes, N-arylhydroxylamine and maleic anhydride. A possible mechanism for the formation of the product is proposed. The reaction was also carried out under microwave irradiation.

  不对称的二芳基胺已经通过甲氧基芳基醛，N-芳基羟胺和马来酸酐之间的新颖的，出乎意料的多组分反应合成。提出了一种可能的产物形成机理。该反应也在微波辐射下进行。
• Pyrrole-2-carboxylic Acid as a Ligand for the Cu-Catalyzed Reactions of Primary Anilines with Aryl Halides
  作者：Ryan A. Altman、Kevin W. Anderson、Stephen L. Buchwald

  DOI：10.1021/jo8008676

  日期：2008.7.1

  Pyrrole 2-carboxylic acid (L5) was found to be an effective ligand for the Cu-catalyzed monoarylation of anilines with aryl iodides and bromides. Under the reported conditions (10% CuI/20% L5/DMSO/K(3)PO(4)/80-100 degrees C/20-24 h), a variety of useful functional groups were tolerated, and moderate to good yields of the diaryl amine products were obtained.
• Barton, Derek H. R.; Donnelly, Dervilla, M. X.; Finet, Jean-Pierre, Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2095 - 2102
  作者：Barton, Derek H. R.、Donnelly, Dervilla, M. X.、Finet, Jean-Pierre、Guiry, Patrick J.

  DOI：——

  日期：——
• Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids
  作者：Joaquín Tamariz、Rafael Bautista、Alberto Jerezano

  DOI：10.1055/s-0032-1317175

  日期：——

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.