1-(2-iodophenyl)-3-p-tolylurea | 710316-98-6

• 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-p-tolylurea
• 英文别名: 1-(2-iodophenyl)-3-(4-methylphenyl)urea
• CAS: 710316-98-6
• 化学式: C₁₄H₁₃IN₂O
• mdl: MFCD04068022
• 分子量: 352.175
• InChiKey: XXJKNQBVQDEAHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  199-201 °C
• 沸点：
  337.3±35.0 °C(Predicted)
• 密度：
  1.691±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-iodophenyl)-3-p-tolylurea 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90%的产率得到1-(p-tolyl)-1H-benzo[d]imidazol-2(3H)-one
  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 、 对甲苯异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-(2-iodophenyl)-3-p-tolylurea
  参考文献：
  名称：

  金（I）催化级联反应合成多环吲哚骨架

  摘要：

  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。

  DOI：

  10.1002/chem.201303539

文献信息

• Leveraging cascade alkynyl Prins cyclization towards the stereoselective synthesis of spiro-furan quinazolinone scaffolds
  作者：Subhamoy Biswas、Sudip Shit、Bipin Kumar Behera、Archana Kumari Sahu、Anil K. Saikia

  DOI：10.1039/d3cc04464e

  日期：——

  spiro-furan quinazolinones employing alkynol urea derivatives utilizing alkynyl Prins cyclization reaction. This methodology produces highly functionalized spiro-heterocycles in excellent yields with exclusive E-selectivity under ambient conditions. Furthermore, late-stage modifications incorporate bromide and acetyl functionalities into the synthesized spiro-heterocycles.

  已经公布了一种 TfOH 促进的无金属方案，用于利用炔基 Prins 环化反应，使用炔醇脲衍生物合成螺呋喃喹唑啉酮。该方法在环境条件下以优异的产率产生高度官能化的螺杂环，并具有独特的E选择性。此外，后期修饰将溴化物和乙酰基官能团纳入合成的螺杂环中。
• 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.
• Synthesis and Reactivity of Ortho-Palladated Arylureas. Synthesis and Catalytic Activity of a C,N,C Pincer Complex. Stoichiometric Syntheses of Some N-Heterocycles
  作者：José Vicente、José-Antonio Abad、Joaquín López-Serrano、Peter G. Jones、Carmen Nájera、Luis Botella-Segura

  DOI：10.1021/om050451y

  日期：2005.10.1

  1-(2-lodophenyl)-3-p-tolylurea (1) reacts with Pd(dba)(2) ([Pd-2(dba)(3)]-dba; dba = dibenzylideneacetone) in the presence of the appropriate ligands to give the ortho-palladated arylureas [PdC6H4NHC(O)NHTo-2}IL2] (To = C6H4Me-4; L-2 = tbubpy (4,4'-di-tert-butyl-2,2'-bipyridine) (2a), tmeda (N,N,N ',N '-tetramethylethylenediamine) (2b); L = PPh3 (2c)). Reaction of 2b with Tl(TfO) TfO = triflate, CF3SO3) results in the formation of cyclopalladated [Pdkappa C-2,O- C6H4NHC(O)NHTo-2}(tmeda)]OTf (3b). The latter reacts with PPh3 to yield [PdC6H4NHC-(O)NHTo-2}(tmeda)(PPh3)]OTf (4b). Treatment of 2b with CO gives the corresponding acyl derivative [PdC(O)C6H4NHC(O)NHTo-2}I(tmeda)] (5b). If Tl(TfO) is added after the bubbling of CO, the C,N coupling product 3-p-tolyl-1H-quinazoline-2,4-dione (6) is formed. Complex 5b reacts with XyNC (Xy = 2,6-dimethylphenyl) to yield trans- [PdC(O)C6H4NHC-(O)NHTo-2}I(CNXy)(2)] (7). Both 5b and 7 decompose in solution to give 6. Complex 2b reacts with isocyanides to give the iminoacyl derivatives trans-[PdC(=NR)C6H4NHC(O)NHTo-2}I(CNR)2] (R = Xy (8x), Bu-t (8t)). The complex 8x gives the C,N coupling product 4-(xylylimino)-3-p-tolyl-3,4-dihydro-1H-quinazolin-2-one (9) after treatment with TlOTf 8x also reacts with bases (K2CO3 and Tl2CO3) to yield the iminoacyl amido carbene C,N,C pincer palladium complex [Pdkappa C-3,N,C-C(=NXy)C6H4NC(O)NToC(NHXy)-2}(CNXy)] (10); this complex is an active precatalyst in Heck and Suzuki reactions. The reaction of 2b with R'C equivalent to CR" and TIOTf gives [Pdkappa C-2,N-CR'=CR"C6H4NHC(O)NHTo-2}(tmeda)]OTf (R' = R" = Et (11be), CO2Me (11bm), Ph (11bp); R' = Ph, R" = CO2Me (11bq)). These complexes decompose in solution, and in the case of 11bp, 2,3-diphenylindole-l-carboxylic acid p-tolylamide (12p) was isolated. 11bq reacts with PPh3 to give 3-phenyl-1H-indole-2carboxylic acid methyl ester (13q). 11bp and 11bq decompose in the presence of CO to yield 3,4-diphenyl-2-quinolone (14po) and 2-oxo-4-phenyl-1,2-dihydroquinoline-3-carboxylic acid methyl ester (14qo), respectively. Similarly, when 11bq is reacted with XyNC, the C,N coupling compound 2-xylyl-4-phenyl-1,2-dihydroquinoline-3-carboxylic acid methyl ester (14qnx) is formed. The crystal and molecular structures of 3b, 10-0.5CDCl(3), 11bp-OEt2, 11bq, and 14po have been determined.
• 10.1039/d4nj01745e
  作者：Biswas, Subhamoy、Bora, Surjya Kumar、Arandhara, Pallav Jyoti、Saikia, Anil K.

  DOI：10.1039/d4nj01745e

  日期：——