1-acetyl-1,3-di-(p-bromophenyl)urea | 134835-91-9

• 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-1,3-di-(p-bromophenyl)urea
• 英文别名: 1-acetyl-1,3-di(4-bromophenyl)urea；N-(4-bromophenyl)-N-((4-bromophenyl)carbamoyl)acetamide；N-acetyl-N,N'-bis-(4-bromo-phenyl)-urea；N-Acetyl-N,N'-bis-(4-brom-phenyl)-harnstoff；N-(4-bromophenyl)-N-[(4-bromophenyl)carbamoyl]acetamide
• CAS: 134835-91-9
• 化学式: C₁₅H₁₂Br₂N₂O₂
• 分子量: 412.08
• InChiKey: MKDORLRJAODBII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-1,3-di-(p-bromophenyl)urea 生成 4'-溴乙酰苯胺
  参考文献：
  名称：

  BOBK, M. V.;SAMARAJ, L. I., YKP. XIM. ZH, 56,(1990) N2, S. 1313-1316

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-双(4-溴苯基)硫脲 、 manganese triacetate 以 乙腈 为溶剂， 反应 3.0h， 以88%的产率得到1-acetyl-1,3-di-(p-bromophenyl)urea
  参考文献：
  名称：

  Regioselective synthesis of N-acetylureas by manganese(III) acetate reaction of 1,3-disubstituted thioureas

  摘要：

  Reactions of asymmetrical 1,3-disubstituted thioureas with manganese(III) acetate produce regioselective N-acetylureas. A mechanism for this novel transformation is proposed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.013

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。
• Regioselective Acetylate of 1,3-Disubstituted Selenoureas Promoted by Recyclable Ion-Supported Hypervalent Iodine(III) Reagent
  作者：Yuanyuan Xie、Haixuan Pan

  DOI：10.1080/10426507.2013.797418

  日期：2014.1

  environmentally friendly reaction of 1,3-disubstituted selenoureas with a recyclable ion-supported hypervalent iodine(III) reagent produces regioselectively N-acetylureas. This is the first example of ion-supported hypervalent iodine reagent [dibmim]+[BF4]−being employed as an N-acetylating agent. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and

  摘要 1,3-二取代硒脲与可回收的离子负载高价碘 (III) 试剂通过温和、高效且环保的反应生成区域选择性 N-乙酰脲。这是离子支持的高价碘试剂 [dibmim]+[BF4]-用作 N-乙酰化剂的第一个例子。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• 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。
• 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.
• 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).