N-phenyl-N'-(2-methoxybenzenecarbonyl)urea | 95461-02-2

• 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-phenyl-N'-(2-methoxybenzenecarbonyl)urea
• 英文别名: 2-methoxy-N-(phenylcarbamoyl)benzamide；N-((2-methoxyphenyl)carbamoyl)benzamide
• CAS: 95461-02-2
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: WCXONWKVFDFOEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  水杨酰胺 在 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 N-phenyl-N'-(2-methoxybenzenecarbonyl)urea
  参考文献：
  名称：

  Design and synthesis of new potassium channel activators derived from the ring opening of diazoxide: Study of their vasodilatory effect, stimulation of elastin synthesis and inhibitory effect on insulin release

  摘要：

  Benzenesulfonylureas and benzenesulfonylthioureas, as well as benzenecarbonylureas and benzenecarbonylthioureas, were prepared and evaluated as myorelaxants on 30 mM KCl-precontracted rat aortic rings. The most active compounds were further examined as stimulators of elastin synthesis by vascular smooth muscle cells and as inhibitors of insulin release from pancreatic beta-cells. The drugs were also characterized for their effects on glycaemia in rats. Benzenesulfonylureas and benzenesulfonylthioureas did not display any myorelaxant activity on precontracted rat aortic rings. Such an effect could be attributed to their ionization at physiological pH. By contrast, almost all benzenecarbonylureas and benzenecarbonylthioureas displayed a myorelaxant activity, in particular the benzenecarbonylureas with an oxybenzyl group linked to the ortho position of the phenyl ring. The vasodilatory activity of the most active compounds was reduced when measured in the presence of 80 mM KCl or in the presence of 30 mM KCl and 10 mu M glibenclamide. Such results suggested the involvement, at least in part, of K-ATP channels. Preservation of a vasodilatory activity in rat aortic rings without endothelium indicated that the site of action of such molecules was located on the vascular smooth muscle cells and not on the endothelial cells. Some of the most active compounds also stimulated elastin synthesis by vascular smooth muscle cells. Lastly, most of the active vasorelaxant drugs, except 15k and 15t at high concentrations, did not exhibit marked inhibitory effects on the insulin releasing process and on glycaemia, suggesting a relative tissue selectivity of some of these compounds for the vascular smooth muscle. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.043

文献信息

• N-Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor
  作者：Vinod K. Tiwari、Mangal S. Yadav、Sumt K. Singh、Anand K. Agrahari、Anoop S. Singh

  DOI：10.1055/a-1399-3823

  日期：2021.7

  found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.

  通过在合适的叠氮化物供体二苯磷酰基叠氮化物（DPPA）存在下，使N-酰基苯并三唑分别与胺或酰胺或酚或硫醇反应，可以合成高至优等收率的各种尿素，N-酰基脲，氨基甲酸酯和硫代氨基甲酸酯。在110°C的无水甲苯中浸泡3-4小时。在此途径中，发现DPPA是库尔蒂乌斯降解中叠氮化物供体的三甲基叠氮化硅和叠氮化钠的良好替代品。高反应产率，一锅法和无金属条件，性质简单，易于处理，使用现成的试剂以及在许多情况下避免使用柱色谱法是该设计方案的显着特征。
• Condensation of acyl chloride on sodium cyanate : preparation of acyl isocyanates
  作者：M.-Z. Deng、P. Caubere、J.P. Senet、S. Lecolier

  DOI：10.1016/s0040-4020(01)89797-0

  日期：1988.1

  The catalytic effects of various metal halides and solvents on the reaction of benzoyl chloride with sodium cyanate were studied. It has been found that SnCl4, and ZnCl2. catalyze the reaction to give the corresponding acyl isocyanates in good yields. The scope of the reaction was studied and a number of aroyl isocyanates and their derivatives were prepared. A few non aromatic isocyanates and their

  研究了各种金属卤化物和溶剂对苯甲酰氯与氰酸钠反应的催化作用。已经发现SnCl 4和ZnCl 2。催化反应以高收率得到相应的酰基异氰酸酯。研究了反应的范围，并制备了许多芳基异氰酸酯及其衍生物。还制备了一些非芳族异氰酸酯及其衍生物。
• DENG, M. -Z.;CAUBERE, P.;SENET, J. P.;LECOLIER, S., TETRAHEDRON, 44,(1988) N 19, C. 6079-6086
  作者：DENG, M. -Z.、CAUBERE, P.、SENET, J. P.、LECOLIER, S.

  DOI：——

  日期：——