1-(4-(trifluoromethyl)benzyl)urea | 296277-64-0

• 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-(4-(trifluoromethyl)benzyl)urea
• 英文别名: [4-(Trifluoromethyl)phenyl]methylurea
• CAS: 296277-64-0
• 化学式: C₉H₉F₃N₂O
• mdl: MFCD17237694
• 分子量: 218.178
• InChiKey: AHKMQKHWBPNHAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-(trifluoromethyl)benzyl)urea 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.5h， 生成 1-(4-methylbenzyl)-6-(methylthio)-3-(4-(trifluoromethyl)benzyl)-1,3,5-triazine-2,4(1H,3H)-dione
  参考文献：
  名称：

  A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists

  摘要：

  A new efficient synthetic method to obtain prokineticin receptor antagonists based on the triazinedione scaffold is described. In this procedure the overall yield improves from 13% to about 54%, essentially for two factors: 1) N-(chlorocarbonyl) isocyanate is no more used, it represents the yield limiting step with an average yield not exceeding 30%. 2) The Mitsunobu reaction is not involved in the new synthetic scheme avoiding the use of time and solvent consuming column chromatography. All synthesized triazinediones were preliminary pharmacologically screened in vivo for their ability to reduce the Bv8-induced thermal hyperalgesia. In this assay all compounds displayed EC50 values in the picomolar-subpicomolar range, some triazinediones containing a 4-halogen substituted benzyl group in position 5 showed the best activity. The analogues containing a 4-fluorine atom (PC-7) and a 4-bromobenzyl group (PC-25) resulted 10 times more potent than the reference PC-1 that bears a 4-ethylbenzyl group. While the 4-trifluoromethylbenzyl substituted analog (PC-27) was 100 times more potent as compared to PC1. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.030
• 作为产物：
  描述：

  potassium cyanate 、 4-(三氟甲基)苄胺 在 氯化铵 作用下， 以 水 为溶剂， 反应 0.25h， 以74%的产率得到1-(4-(trifluoromethyl)benzyl)urea
  参考文献：
  名称：

  氯化铵促进微波辐照下单取代脲的快速合成

  摘要：

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。

  DOI：

  10.1002/ejoc.202101059

文献信息

• [EN] COMPOUND LIBRARIES OF N-(AMINOCARBONYL)-PIPERIDINE-4-CARBOXAMIDE DERIVATIVES CAPABLE OF BINDING TO G-PROTEIN COUPLED RECEPTORS<br/>[FR] BANQUE DE COMPOSES CONTENANT DES DERIVES DE N-(AMINOCARBONYL)-PIPERIDINE-4-CARBOXAMIDE, CAPABLES DE SE FIXER AUX RECEPTEURS COUPLES A LA PROTEINE G
  申请人：BIOFOCUS PLC

  公开号：WO2004058259A1

  公开（公告）日：2004-07-15

  The present invention provides a compound library targeted to receptors with a requirement for a positively charged amine in their structure activity relationships. It is designed to produce both agonists and antagonists and so is expected to be especially useful in producing ligands for orphan receptors. The library is designed around an acylurea coupled to a piperidine moiety. A combination of specific motifs R2 and R1 are appended from the central scaffold and are designed to pick up different interactions at a receptor site. The library comprises or consists of a set of structurally related compounds of general formula (I).

  本发明提供了一个针对需要带正电胺基的受体的化合物库，该化合物库旨在产生激动剂和拮抗剂，因此预计在制备孤儿受体的配体方面特别有用。该库围绕一个酰基脲偶联到哌啶基团而设计。从中心支架附加特定基团R2和R1的组合被设计为在受体位点捕获不同的相互作用。该库包括或由一组结构相关的通用式(I)化合物组成。
• [EN] THIADIAZOLONE DERIVATIVES USEFUL IN THE TREATMENT OF DIABETES<br/>[FR] DÉRIVÉS DE THIADIAZOLONE UTILES DANS LE TRAITEMENT DU DIABÈTE
  申请人：BALTIC BIO AB

  公开号：WO2013108026A1

  公开（公告）日：2013-07-25

  According to the invention there is provided a compound of formula I, wherein, R1 to R4 have meanings given in the description, which compounds are useful in the treatment of diabetes.

  根据本发明提供了一种I式化合物，其中R1到R4的含义如描述中所给，这些化合物在糖尿病治疗中有用。
• Regioselective Synthesis of Benzimidazolones via Cascade C–N Coupling of Monosubstituted Ureas
  作者：Johannes B. Ernst、Nicholas E. S. Tay、Nathan T. Jui、Stephen L. Buchwald

  DOI：10.1021/ol501531q

  日期：2014.7.18

  A direct method for the regioselective construction of benzimidazolones is reported wherein a single palladium catalyst is employed to couple monosubstituted urea substrates with differentially substituted 1,2-dihaloaromatic systems. In this method, the catalyst is able to promote a cascade of two discrete chemoselective C-N bond-forming processes that allows the highly selective and predictable formation of complex heterocycles from simple, readily available starting materials.
• EP1725238A4
  申请人：——

  公开号：EP1725238A4

  公开（公告）日：2009-04-01
• M 3 MUSCARINIC ACETYLCHOLINE RECEPTOR ANTAGONISTS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1725238A2

  公开（公告）日：2006-11-29