N-(3-氯苯基)-氰胺 | 54507-99-2

• 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: N-(3-氯苯基)-氰胺
• 英文名称: 3-chlorophenyl cyanamide
• 英文别名: N-(3-chlorophenyl)cyanamide；N-(3-Chlorophenyl)-cyanamide；(3-chlorophenyl)cyanamide
• CAS: 54507-99-2
• 化学式: C₇H₅ClN₂
• mdl: MFCD12402220
• 分子量: 152.583
• InChiKey: DCMFSSNEAKEHAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-氯苯基)-氰胺 在 水 作用下， 反应 0.83h， 以92%的产率得到M-氯苯基脲
  参考文献：
  名称：

  A green and facile approach for the synthesis of N-monosubstituted ureas in water: Pd catalyzed reaction of arylcyanamides (an unexpected behavior of electron withdrawing groups)

  摘要：

  The Fe3O4 magnetic nano-particles were prepared, coated with tetraethyl orthosilicate (TEOS), functionalized with 3-chloropropyltrimethoxysilane (CPTMS), further functionalized with 2,2'-(piperazine-1,4-diylbis(methylene) dianiline (PDMD) and the corresponding Pd complex synthesized as a novel nano-magnetic heterogeneous catalyst (Fe3O4@SiO2@CPTMS@PDMD@Pd) to be used for the synthesis of various N-monosubstituted ureas in water.Also, in another attempt to see the effect of HCOOH, the hydration reaction of arylcyanamide was carried out in the presence of HCOOH (water + 98% HCOOH) which had two effects: it decreased the amount of the Pd catalyst from 40 to 30 mg, and the reaction condition was changed from the reflux condition to room temperature.Interestingly, the arylcyanamides with electron withdrawing groups influence the course of the reaction and need more reaction times for completion which is an unexpected behavior, probably due to the high electron density around the central carbon atom of the nitrile group. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.05.049
• 作为产物：
  描述：

  1-(3-氯苯基)-2-硫脲 在 碳酸氢钠 、 tetrapropylammonium tribromide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.08h， 生成 N-(3-氯苯基)-氰胺
  参考文献：
  名称：

  使用环境友好的试剂四丙基三溴化铵从二硫代氨基甲酸酯盐中新颖合成一锅法合成异硫氰酸酯和氰胺。

  摘要：

  描述了在温和，有效且无毒的三溴化四铵铵存在下，由它们各自的胺合成异硫氰酸酯和氰胺的高效简单方法。试剂的高环境可接受性，成本效益和高产率是该方法的重要属性。

  DOI：

  10.17344/acsi.2017.3342

文献信息

• Copper-Catalyzed One-Pot Synthesis of Unsymmetrical Arylurea Derivatives via Tandem Reaction of Diaryliodonium Salts with <i>N</i>-Arylcyanamide
  作者：Pengfei Li、Guolin Cheng、Hong Zhang、Xianxiang Xu、Jingyuan Gao、Xiuling Cui

  DOI：10.1021/jo501334u

  日期：2014.9.5

  efficient “one-pot” approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples

  已经提出了一种有效的“一锅法”，用于从N-芳基氰酰胺和二芳基碘鎓盐中制备多种取代的尿素。该两步过程涉及仲胺与二芳基碘鎓的弱碱促进的化学选择性芳基化和第二仲芳基碘鎓的铜催化的N-芳基氰酰胺的亲核加成。对于29个实施例，以高达91％的收率获得了各种不对称的芳基脲。
• Palladium and Lewis-Acid-Catalyzed Intramolecular Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene Difunctionalizations
  作者：Zhongda Pan、Shengyang Wang、Jason T. Brethorst、Christopher J. Douglas

  DOI：10.1021/jacs.8b01330

  日期：2018.3.7

  An expansion of methodologies aimed at the formation of versatile organonitriles, via the intramolecular aminocyanation of unactivated alkenes, is herein reported. Importantly, the need for a rigid tether in these reactions has been obviated. The ease-of-synthesis and viability of substrates bearing flexible backbones has permitted for diastereoselective variants as well. We demonstrated the utility

  本文报道了旨在通过未活化烯烃的分子内氨基氰化形成多功能有机腈的方法的扩展。重要的是，在这些反应中不需要刚性系绳。带有柔性主链的底物的合成容易性和生存能力也允许非对映选择性变体。我们通过形成吡咯烷酮、哌啶酮、异吲哚酮和舒尔坦证明了这种方法的实用性。此外，还证明了这些基序随后转化为医学相关分子。双交叉 13C 标记实验与完全分子内环化机制一致。氘标记实验支持涉及跨烯烃的顺式加成的机制。
• Bromineless Bromine as an Efficient Desulfurizing Agent for the Preparation of Cyanamides and 2-Aminothiazoles from Dithiocarbamate Salts
  作者：Ramesh Yella、Veerababurao Kavala、Bhisma K. Patel

  DOI：10.1080/00397911003642658

  日期：2011.2.28

  desulfurizing agent in the preparation of organic cyanamides and substituted thiazoles starting from dithiocarbamic acid salts. In this approach, alkyl/aryl isothiocyantes were first obtained by the desulfurization of dithiocarbamic acid salts with EDPBT. The in situ–generated isothiocyanates reacts with an aqueous ammonia, forming alkyl or aryl thioureas, which on subsequent oxidative desulfurization

  摘要 在以二硫代氨基甲酸为原料制备有机氰胺和取代噻唑的过程中，无溴溴化试剂 1,1'-(乙烷-1,2-二基)二溴化吡啶鎓 (EDPBT) 已被用作脱硫剂。盐。在这种方法中，烷基/芳基异硫氰酸酯首先通过二硫代氨基甲酸盐与 EDPBT 脱硫获得。原位生成的异硫氰酸酯与氨水反应，形成烷基或芳基硫脲，随后用 EDPBT 氧化脱硫，以良好的收率形成相应的氰胺。或者，通过原位生成的 1-芳基硫脲与由酮原位生成的 α-溴酮缩合，再次使用 EDPBT，实现了取代噻唑的高效一锅法合成。试剂 EDPBT 可以很容易地从现成的试剂中制备。对于易于溴化的底物，脱硫能力优于其溴化能力。
• <i>N</i>-Aryl <i>N</i>‘-Hydroxyguanidines, A New Class of NO-Donors after Selective Oxidation by Nitric Oxide Synthases:  Structure−Activity Relationship
  作者：Axelle Renodon-Cornière、Sylvie Dijols、Céline Perollier、David Lefevre-Groboillot、Jean-Luc Boucher、Roger Attias、Marie-Agnes Sari、Dennis Stuehr、Daniel Mansuy

  DOI：10.1021/jm011006h

  日期：2002.2.1

  The formation of nitric oxide (NO) was followed during the oxidation of 37 N-hydroxyguanidines or related derivatives, including 18 new N-aryl N'-hydroxyguanidines, by recombinant inducible nitric oxide synthase (NOS II). Several N-aryl N'-hydroxyguanidines bearing a relatively small, electron-donating para subtituent, such as H, F, Cl, CH(3), OH, OCH(3), and NH(2), led to NO formation rates between

  通过重组诱导型一氧化氮合酶（NOS II）氧化37个N-羟基胍或相关衍生物（包括18个新的N-芳基N'-羟基胍）的过程中，形成一氧化氮（NO）。几个带有相对较小的给电子对位取代基的N-芳基N'-羟基胍，例如H，F，Cl，CH（3），OH，OCH（3）和NH（2），导致NO的生成速率N（ω）-羟基-L-精氨酸（NOHA）生成的NO的8％至41％。这些反应的特征与先前报道的NOS氧化NOHA的特征非常相似：（i）严格要求NOS含有（6R）-5,6,7,8-四氢-L-生物蝶呤，烟酰胺还原腺嘌呤磷酸二核苷酸和O（2）发生氧化，（ii）以1：1的摩尔比形成NO和相应的尿素，并且（iii）经典的NOS抑制剂（例如N（ω）-硝基-L-精氨酸和S-乙基-异硫氰酸酯）具有很强的抑制作用-硫脲。构效关系研究表明，两个结构因素对于由具有C（三键）NOH功能的化合物形成NO至关重要。第一个是存在单取代的N-羟基胍
• Iron(iii) catalysed synthesis of unsymmetrical di and trisubstituted ureas – a variation of classical Ritter reaction
  作者：Hosamani Basavaprabhu、Vommina V. Sureshbabu

  DOI：10.1039/c2ob06916d

  日期：——

  An application of the classical Ritter reaction for the synthesis of unsymmetrical di and trisubstituted ureas catalyzed by FeCl3 is described. The protocol is of significant interest in view of the easy availability of precursors, mild reaction conditions employed and interestingly its applicability for the alkylation of alcohols capable of forming stable carbocationic intermediates even to the sterically hindered moieties.

  介绍了利用经典Ritter反应合成非对称二取代和三取代脲类化合物的方法，该反应由FeCl3催化。该方案具有重要意义，因为其前体易于获得，反应条件温和，而且在对能够形成稳定碳正离子中间体的醇进行烷基化时，即使是空间位阻较大的基团也能适用。