1,3-二苯基-1-丙酰脲 | 1017535-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二苯基-1-丙酰脲
• 英文名称: 1,3-diphenyl-1-propionylurea
• CAS: 1017535-62-4
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: SOOCDTWAMDIZGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 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：

  丙酸 、 N,N'-二苯基硫脲 在 lead(II) nitrate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以66%的产率得到1,3-二苯基-1-丙酰脲
  参考文献：
  名称：

  Oxidative desulfurization of disubstituted thioureas using Pb(II) salts and investigation of pK_a-dependent regioselective N-acylation

  摘要：

  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).

  DOI：

  10.1080/17415990903295686

文献信息

• Hypervalent Iodine(III)-Mediated Regioselective N-Acylation of 1,3-Disubstituted Thioureas
  作者：C. B. Singh、Harisadhan Ghosh、Siva Murru、Bhisma K. Patel

  DOI：10.1021/jo702628g

  日期：2008.4.1

  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.