1-benzyl-3-(m-tolyl)urea | 13143-28-7

• 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: 1-benzyl-3-(m-tolyl)urea
• 英文别名: N-benzyl-N'-(3-methylphenyl)urea；1-benzyl-3-(3-methylphenyl)urea
• CAS: 13143-28-7
• 化学式: C₁₅H₁₆N₂O
• mdl: MFCD00088105
• 分子量: 240.305
• InChiKey: WPMJGFMRVLNWHX-UHFFFAOYSA-N

物化性质

• 沸点：
  379.1±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基苯胺 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 1-benzyl-3-(m-tolyl)urea
  参考文献：
  名称：

  An efficient transformation of ethers to N,N′-disubstituted ureas in a Ritter type reaction

  摘要：

  A simple, mild, and an alternative protocol for the preparation of N,N'-disubstituted ureas from readily available ethers and cyanamides as starting materials is described. The protocol explores the reactivity of ether in a Ritter type reaction with cyanamide in the presence of BF3 center dot Et2O and resulting in the formation of N,N'-disubstituted urea. Divinyl ether as well as MTBE (methyl tert-butyl ether) can be employed as ether components to afford allyl and tert-butyl ureas respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.027

文献信息

• Pd/C-Catalyzed Domino Synthesis of Urea Derivatives Using Chloroform as the Carbon Monoxide Source in Water
  作者：Liang Wang、Hao Wang、Guiqing Li、Shuliang Min、Fangyuan Xiang、Shiqi Liu、Waigang Zheng

  DOI：10.1002/adsc.201800954

  日期：2018.12.3

  A Pd/C‐catalyzed domino synthesis of symmetrical and unsymmetrical ureas from aryl iodides, sodium azide, amines and CHCl3 in water has been developed. This reaction proceeds with sequential carbonylation, Curtius rearrangement and nucleophilic addition. CHCl3 serves as a convenient and safe alternation of CO gas in the presence of KOH. A series of urea derivatives were obtained in moderate to good

  已经开发了一种Pd / C催化由水中的芳基碘化物，叠氮化钠，胺和CHCl 3合成对称和不对称脲的多米诺骨牌。该反应以顺序的羰基化，Curtius重排和亲核加成进行。在KOH存在下，CHCl 3可作为一种方便，安全的CO气体替代气体。以中等至良好的产率获得了具有良好的官能团耐受性的一系列脲衍生物。此外，连续六次运行后，Pd / C催化剂很容易被回收，催化活性略有下降。
• <scp>Pd‐Catalyzed<i>Ortho</i>‐Directed</scp>C—H Glycosylation of Arenes Using N‐linked Bidentate Auxiliaries
  作者：Quanquan Wang、Wanjun Zhu、Qikai Sun、Gang He、Gong Chen

  DOI：10.1002/cjoc.202000500

  日期：2021.3

  A set of Pd‐catalyzed ortho‐directed C—H glycosylation reactions with glycosyl chloride donors using various N‐linked bidentate auxiliaries has been developed for synthesis of C‐aryl glycosides. A broad range of pyranose and furanose moieties can be installed on the ortho position of arylamine, carbazole, indole and benzylamine type substrates in high yield and with high regio‐ and diastereoselectivity

  已经开发了一组使用各种N-连接的双齿状助剂的Pd催化的邻位C-H糖基化反应与糖基氯供体的反应，用于合成C-芳基糖苷。可以在芳胺，咔唑，吲哚和苄胺类底物的邻位上以高收率，高区域选择性和非对映选择性的方式安装各种吡喃糖和呋喃糖部分。这些助剂可以在相对温和的条件下轻松安装和拆卸。
• Photocatalyzed synthesis of unsymmetrical ureas via the oxidative decarboxylation of oxamic acids with PANI-g-C3N4-TiO2 composite under visible light
  作者：Liang Wang、Hao Wang、Yaoyao Wang、Minggui Shen、Shubai Li

  DOI：10.1016/j.tetlet.2020.151962

  日期：2020.6

  The synthesis of unsymmetrical ureas via the photocatalyzed oxidative decarboxylation of oxamic acids has been developed. The carbamoyl radicals were generated from oxamic acids in the presence of a hypervalent iodine reagent and the PANI(Polyaniline)-g-C3N4-TiO2 composite under visible light irradiation. The radicals were converted in situ into the corresponding isocyanates, which were then trapped

  已经开发了通过光催化的草酰胺酸氧化脱羧合成不对称脲的方法。在高价碘试剂和PANI（聚苯胺）-gC 3 N 4 -TiO 2复合材料的存在下，由草酰胺酸在可见光照射下生成氨基甲酰基自由基。自由基被原位转化进入相应的异氰酸酯，然后被胺捕获，以中等至良好的产率得到相应的产物。该方案避免了直接使用对环境不利的异氰酸酯，并且可以耐受一系列底物。而且，光催化剂可以通过简单的过滤而容易地回收，并且可以在仅轻微降低催化活性的情况下重复使用几次。
• Ion-exchange resins for solution phase parallel synthesis of chemical libraries
  作者：Leah M. Gayo、Mark J. Suto

  DOI：10.1016/s0040-4039(96)02362-3

  日期：1997.1

  Described are various techniques that employ ion-exchange resins for the solution-phase synthesis of chemical libraries. We have found these resins to be useful as reagents and/or scavengers in a variety of reactions. Nine basic ion-exchange resins were evaluated for the catalysis and purification of an amide synthesized from an acid chloride. A number of the resins examined provided products in >95%

  描述了使用离子交换树脂用于化学库的溶液相合成的各种技术。我们发现这些树脂在各种反应中可用作试剂和/或清除剂。评价了九种碱性离子交换树脂对由酰氯合成的酰胺的催化和纯化。所检查的许多树脂提供的产品纯度均超过95％。酸性离子交换树脂也可用作尿素合成中的清除剂。还描述了这些树脂在制备酰胺，酯和脲库中的效用的证明。
• Kanamycin−Cu(II) Complex Catalyzed Ullmann Amine Synthesis at Room Temperature: A Tool for Mechanistic Insights into Methylene Blue Degradation
  作者：Huma Basheer、Sadia Shamsi、Abdul Qadir、Kalicharan Sharma、Chandra S. Azad、Amit Kumar、Imran A. Khan

  DOI：10.1002/ejoc.202400328

  日期：2024.8.5

  The transformative potential of kanamycin−copper (II) complexes for Ullmann amine synthesis at room temperature showcases the efficient creation of diverse N−aryl compounds via SO4−• mediated generation of Cu(III)−aryl species. Additionally, it highlights the catalyst's role in degrading methylene blue, advancing both catalytic methodologies and environmental applications.

  卡那霉素-铜(II) 配合物在室温下用于乌尔曼胺合成的转化潜力展示了通过SO 4 −•介导的Cu(III)−芳基物种的生成来有效产生多种N−芳基化合物。此外，它还强调了该催化剂在降解亚甲基蓝方面的作用，推进了催化方法和环境应用。