1-(2-iodophenyl)-3-(4-methoxyphenyl)urea | 892455-34-4

• 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-(2-iodophenyl)-3-(4-methoxyphenyl)urea
• CAS: 892455-34-4
• 化学式: C₁₄H₁₃IN₂O₂
• mdl: MFCD04279481
• 分子量: 368.174
• InChiKey: YPPJQEZDPNYPCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-iodophenyl)-3-(4-methoxyphenyl)urea 在 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以95%的产率得到1-(p-Methoxyphenyl)benzimidazolon
  参考文献：
  名称：

  Copper-Catalyzed Intramolecular Cyclization to N-Substituted 1,3-Dihydrobenzimidazol-2-ones

  摘要：

  An efficient and convenient method was developed for preparing N-substituted 1,3-dihydrobenzimidazol-2-ones from N'-substituted N-(2-halophenyl)ureas via a Cul/DBU-catalyzed cyclization in DMSO under microwave heating. High yields were obtained and a variety of functional groups were tolerated under these conditions, including N'-aryl, alkyl, heterocyclic, various N-(substituted 2-halophenyl) and N-(2-iodopyridyl)ureas.

  DOI：

  10.1021/ol8011106
• 作为产物：
  描述：

  2-碘苯胺 、 对甲氧基苯异氰酸酯 在 [Ti(tosylimido)(NMe2)2]2 作用下， 以 甲苯 为溶剂， 以76%的产率得到1-(2-iodophenyl)-3-(4-methoxyphenyl)urea
  参考文献：
  名称：

  使用桥联磺酰亚氨基钛 (IV) 配合物催化胺、硫醇和二苯基氧化膦与杂枯烯的加成反应

  摘要：

  我们在此提出了一种有效的加氢元素化反应方法，例如使用对甲苯基磺酰亚胺负载的双核钛配合物对杂枯烯碳二亚胺、芳基异氰酸酯和异硫氰酸酯与苯胺或苯硫酚进行氢胺化、氢硫醇化和氢磷酸化。所有反应均在温和的条件下和较短的反应时间内以优异的收率实现。通过光谱技术分离和充分表征产物。我们还提出了一种在第一步中涉及质子提取（苯胺或苯硫酚的 E-H）的机制。在反应机理中，双核 Ti IV配合物的酰胺基团充当离去基团，而磺酰亚胺键不受影响。

  DOI：

  10.1002/zaac.202200188

文献信息

• Synthesis of Polycyclic Indole Skeletons by a Gold(I)-Catalyzed Cascade Reaction
  作者：Tao Wang、Shuai Shi、Daniel Pflästerer、Eva Rettenmeier、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/chem.201303539

  日期：2014.1.3

  3‐phenylpropargyl alcohols catalyzed by a simple IPr–gold(I) catalyst in a gold(I)‐catalyzed cascade reaction composing of a gold‐catalyzed nucleophilic addition and a subsequent gold‐catalyzed substitution reaction delivers 1H‐imidazo[1, 5−a]indol‐3(2 H)‐ones. Other gold(I) catalysts or silver catalysts gave lower yields and often gave other side products. Gold(III) and copper(II) catalysts decomposed the starting

  在金（I）催化的级联反应中，由简单的IPr-金（I）催化剂催化的简单易得的脲取代的3-苯基丙炔醇的转化，该反应由金催化的亲核加成反应和随后的金催化的取代反应组成反应产生1 H-咪唑并[1，5-a]吲哚-3（2  H）-那些。其他金（I）催化剂或银催化剂给出的收率较低，并且经常得到其他副产物。金（III）和铜（II）催化剂分解了起始原料。提供了十二个实例，包括在尿素亚结构的远端氮上的供体和受体取代基。X射线晶体结构分析确认了结构分配。包括中间体的分离和进一步转化以及与对映体纯原料的反应在内的机理研究表明，在亲核加成步骤后，底物在吲哚醇中间体上经历了S N 1型苄基取代反应，或者在2的分子内进行了氢化反应乙烯基吲哚中间体。
• Platinum-catalyzed consecutive C–N bond formation-[1,3] shift of carbamoyl and ester groups
  作者：Itaru Nakamura、Yusuke Sato、Sayaka Konta、Masahiro Terada

  DOI：10.1016/j.tetlet.2009.02.108

  日期：2009.5

  The reaction of ortho-alkynylphenylureas 1 having a carbamoyl group attached to the nitrogen atom proceeded in the presence of catalytic amounts of Ptl(4), affording corresponding indole-3-carbamides 2 in moderate to high yields. In addition, the platinum-catalyzed cyclization of ortho-alkynylphenyl carbamates 3 afforded corresponding indole-3-carboxylates 4 in good yields. The present reaction proceeds through the intramolecular addition of carbon-nitrogen bonds to triple bonds, the so-called carboamination. (c) 2009 Elsevier Ltd. All rights reserved.
• Continuous Recycling of Homogeneous Pd/Cu Catalysts for Cross-Coupling Reactions
  作者：Siddharth Sharma、K. C. Basavaraju、Ajay K. Singh、Dong-Pyo Kim

  DOI：10.1021/ol501802w

  日期：2014.8.1

  Given the importance of homogeneous catalysts recycling in organic chemistry, we have developed a unique microfluidic loop system for automated continuous recirculation of a soluble polymer supported metal catalyst for novel isocyanide cross-coupling reactions under thermomorphic multicomponent solvent (TMS) conditions. Our system provides an innovative approach for the chemical library synthesis of quinazolinone derivatives as well as an important intermediate of Merck's LTD4 antagonist "Singulair" with efficient continuous homogeneous catalyst recycling.
• Ligand-free palladium assisted insertion of isocyanides to urea derivatives for cascade synthesis of phenylamino-substituted quinazolinones
  作者：Siddharth Sharma、Abhilasha Jain

  DOI：10.1016/j.tetlet.2014.09.027

  日期：2014.10

  Palladium catalyzed cascade coupling of substituted urea derivatives and tert-butyl isocyanide for the efficient synthesis of phenylamino-substituted quinazolinones has been developed in moderate to good yields. This method provides a short and alternative approach for the synthesis of quinazolinones derivatives which are valuable compounds with biological and pharmacological potentials. A plausible mechanistic scheme is proposed. (C) 2014 Elsevier Ltd. All rights reserved.
• Regioselective synthesis of spiro quinazolinones via sequential hydroalkoxylation and intramolecular amide-cyclization of alkynol ureas
  作者：Subhamoy Biswas、Surjya Kumar Bora、Pallav Jyoti Arandhara、Anil K. Saikia

  DOI：10.1039/d4nj01745e

  日期：——

  Highly functionalized spiro-furan/pyran quinazolinones employing a cascade hydroalkoxylation-intramolecular amide-cyclization of alkynol ureas in excellent yields and exclusive regioselectivity have been unveiled.