5-(p-tolylamino)-1,3-benzodioxole | 137445-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(p-tolylamino)-1,3-benzodioxole
• 英文别名: 5-(p-tolylamino)benzo-1,3-dioxole；N-(p-tolyl)-3,4-methylenedioxyaniline；N-(4-tolyl)-3,4-methylenedioxyaniline；N-(p-tolyl)benzo[d][1,3]dioxol-5-amine；N-(4-methylphenyl)-1,3-benzodioxol-5-amine
• CAS: 137445-08-0
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: PWXCLBGEUKIHHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 反应 2.0h， 以145 mg的产率得到5-(p-tolylamino)-1,3-benzodioxole
  参考文献：
  名称：

  无金属条件下苯酚的直接胺化

  摘要：

  在此，我们公开了通过使用胺化试剂直接胺化苯酚来无金属合成芳胺。该反应过程使用容易获得的胺化试剂，并为具有各种官能度的广泛芳胺提供了一种通用的合成途径，收率良好至极好。通过使用胺化和氧化偶联反应的两步路线，我们从两种市售酚类合成了三种天然存在的咔唑生物碱：murrayafoline A、mukonine 和黄花碱。

  DOI：

  10.1055/s-0033-1338703

文献信息

• P^(III)-Promoted Reductive Coupling of Aromatic and Aliphatic Nitro Compounds with Grignard Reagents
  作者：Shan-Shui Meng、Fei Li、Xiaowen Tang、Albert S. C. Chan

  DOI：10.1021/acs.orglett.3c01167

  日期：2023.5.26

  coupling of nitro compounds with Grignard reagents is described. Polyfunctional and pharmaceutically relevant diarylamines were generated by this reaction in moderate to high yields. Aliphatic nitro compounds that are highly challenging substrates undergo a combination of α-arylation and reductive coupling to afford the α-arylated arylamines efficiently. A series of valuable biaryl compounds with polyfluorinated

  描述了硝基化合物与格氏试剂的磷化氢促进还原偶联。通过该反应以中等到高产率生成多官能和药学相关的二芳基胺。脂肪族硝基化合物是极具挑战性的底物，经过 α-芳基化和还原偶联的组合，可以有效地提供 α-芳基化芳基胺。以 56-94% 的收率共同生成了一系列具有多氟化和杂芳基环的有价值的联芳基化合物。
• 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：——
• Nickel-Catalyzed Synthesis of Diarylamines via Oxidatively Induced C–N Bond Formation at Room Temperature
  作者：Laurean Ilies、Tatsuaki Matsubara、Eiichi Nakamura

  DOI：10.1021/ol302688u

  日期：2012.11.2

  A nickel-catalyzed oxidative coupling of zinc amides with organomagnesium compounds selectively produces diarylamines under mild reaction conditions, with tolerance for chloride, bromide, hydroxyl, ester, and ketone groups. A diamine is bis-monoarylated. A bromoaniline undergoes N-arylation followed by Kumada-Tamao-Corriu coupling in one pot. The reaction may proceed via oxidatively induced reductive elimination of a nickel species.
• ——
  作者：G. Boyer、M. Giorgi、F. Chatel、J. P. Galy

  DOI：10.1023/a:1021860410863

  日期：——

  The structural determination by X-ray crystallography of the titled N-arylamine 4a, as well as AM(1) calculations on a series of derivatives (4b-c, 5a-c), are reported. The compound 4a is monoclinic P2(1)/c with a = 7.656(3), b = 23.655(5), c = 7.686(9) Angstrom, beta = 112.59(6)degrees, V = 1285.2(2) Angstrom(3) and Z = 4. This structure has been used as a template for the building of some others derivatives used for AM(1) calculations. The results show that the cyclization position on the aromatic rings, which can lead to two regioisomers, depends on the nature of the benzylic substituants.
• Direct Amination of Phenols under Metal-Free Conditions
  作者：Jun Wu、Jianzhong Yu、Yongtao Wang、Peizhi Zhang

  DOI：10.1055/s-0033-1338703

  日期：——

  Herein, we disclose the metal-free synthesis of arylamines via the direct amination of phenols using aminating reagents. This reaction procedure uses easy accessible aminating reagents and provides a versatile synthetic route to a broad range of arylamines with various functionalities in good to excellent yield. By using a two-step route of amination and oxidative coupling reaction, we synthesized

  在此，我们公开了通过使用胺化试剂直接胺化苯酚来无金属合成芳胺。该反应过程使用容易获得的胺化试剂，并为具有各种官能度的广泛芳胺提供了一种通用的合成途径，收率良好至极好。通过使用胺化和氧化偶联反应的两步路线，我们从两种市售酚类合成了三种天然存在的咔唑生物碱：murrayafoline A、mukonine 和黄花碱。