1-acetyl-1-phenyl-3-p-tolylurea | 1017535-54-4

• 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-acetyl-1-phenyl-3-p-tolylurea
• 英文别名: 1-acetyl-1-phenyl-3-(4-methylphenyl)urea
• CAS: 1017535-54-4
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: NNAPKJXUDWMTRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  碘苯二乙酸 、 1-(4-甲基苯基)-3-苯基硫脲 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 1-acetyl-1-p-tolyl-3-phenylurea 、 1-acetyl-1-phenyl-3-p-tolylurea
  参考文献：
  名称：

  Hypervalent Iodine(III)-Mediated Regioselective N-Acylation of 1,3-Disubstituted Thioureas

  摘要：

  Reaction of asymmetrical 1,3-disubstituted thioureas with diacetoxyiodobenzene (DIB) produces regioselectively N-acetylurea in shorter time. Regioselectivity is dependent on the pK(a)'s of the amine attached to the thiourea moiety with acylation taking place toward the an-tine having a lower pK(a). This is the first example of DIB being employed as an N-acetylating agent. A mechanism for this novel transformation is also proposed. Mild reaction conditions, shorter reaction times, high efficiencies, environmentally benign methods, and facile isolation of the desired product make the present methodology a most suitable alternative.

  DOI：

  10.1021/jo702628g

文献信息

• Zinc Acetate-Mediated Regioselective N-Acylation of 1,3-Disubstituted Selenoureas
  作者：Xue Li、Bin Gan、Zhixiang Peng、Zhisheng Mi、Yuanyuan Xie

  DOI：10.3184/174751918x15260514562361

  日期：2018.6

  N-acetylureas were synthesised regioselectively from 1,3-disubstituted selenoureas and zinc acetate. Regioselectivity was dependent on the pKa of the amine attached to the selenourea and occurred towards the amine with the lower pKa. The approach provided a simple, mild and efficient way to construct various N-acetylureas regioselectively in moderate to good yields (53–88%). A plausible mechanism was

  N-乙酰脲是由 1,3-二取代硒脲和乙酸锌区域选择性合成的。区域选择性取决于附着在硒脲上的胺的 pKa，并且发生在 pKa 较低的胺上。该方法提供了一种简单、温和且有效的方法，可以区域选择性地构建各种 N-乙酰脲，收率中等至良好（53-88%）。提出了形成 N-乙酰脲的合理机制。
• One-pot synthesis of N-acylated ureas using phenyliodine (III) diacetate (PIDA) as N-acylation agent
  作者：Rong Feng、Lang Huang、Da-Bin Qin、Fang Zhou、Zhi-Bing Dong

  DOI：10.1016/j.tetlet.2023.154694

  日期：2023.9

  An effective method was explored for the one-pot synthesis of N-acylated urea derivatives by the reaction of substituted isothiocyanatobenzenes, primary amines and PIDA (phenyliodine (III) diacetate) in one-pot manner. Mild reaction conditions, short reaction time, high efficiency and readily accessible materials are the features of this method, making suitable and alternative for the preparation of

  探索了一种由取代异硫氰酸苯、伯胺和PIDA（二乙酸苯碘(III)）一锅法反应一锅法合成N-酰化脲衍生物的有效方法。该方法具有反应条件温和、反应时间短、效率高、原料易得等特点，适用于多种生物或药物活性化合物的制备。
• Oxidative desulfurization of disubstituted thioureas using Pb(II) salts and investigation of p<i>K</i>_a-dependent regioselective N-acylation
  作者：Harisadhan Ghosh、Soumya Sarkar、Abdur Rezzak Ali、Bhisma K. Patel

  DOI：10.1080/17415990903295686

  日期：2010.2

  A highly efficient method for the N-acylation of both symmetrical and unsymmetrical thioureas by the use of lead (II) salts and triethylamine has been achieved. The reaction gives regioselective N-acylated product for unsymmetrical thiourea. For unsymmetrical thiuourea, regioselective N-acylation takes place towards the amine having lower pKa. A linear correlation between the pKas of the amines and the regioselective N-acylation is found. Another attractive feature of this transformation is that lead sulfide, which is important to material science, is obtained as a side product (nanocubes of 20nm).