4-cyanophenylcyanamide

• 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: 4-cyanophenylcyanamide
• 英文别名: 4-(cyanoamino)benzonitrile；(4-cyanophenyl)cyanamide
• 化学式: C₈H₅N₃
• 分子量: 143.148
• InChiKey: DBTWGHCQUSGRNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 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：
  59.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyanophenylcyanamide 在 ammonium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 生成 1-(4-cyanophenyl) 2-iminohydantoin
  参考文献：
  名称：

  Novel and green protocol for the synthesis of 2-iminohydantoins

  摘要：

  A novel and green protocol for the synthesis of N-1 and C-5 substituted 2-iminohydantoins has been developed. Methyl N-cyano-N-alkyl/aryl-aminoacetate reacts with aqueous ammonia at room temperature in 10-30 min. The developed protocol does not require any work-up for the isolation or purification of the products; simple filtration can lead to the pure products in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.057
• 作为产物：
  描述：

  4-异氰基苯甲腈 在 叠氮基三甲基硅烷 、 [Au(MeCN)(PPh₃)][SbF₆] 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到4-cyanophenylcyanamide
  参考文献：
  名称：

  异氰化物的选择性金催化氰胺和1取代的1H-替硝唑-5-胺的合成

  摘要：

  新发现的金催化的异氰化物与由三甲基甲硅烷基叠氮化物和甲醇（或由NaN 3 / AcOH产生）就地生成的氢氰酸反应，可生成氰胺或1取代的1 H-四唑-5-胺，具体取决于可用HN量3。该反应选择性地进行，并且两种产物的收率通常都很高，因此特别方便地获得了广泛的取代1 H-四唑-5-胺，而这些胺否则很难获得。

  DOI：

  10.1002/chem.201803252

文献信息

• Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles
  作者：Mohan Seelam、Prasada Rao Kammela、Bajivali Shaikh、Ramana Tamminana、Sujatha Bogiri

  DOI：10.1007/s10593-018-2303-1

  日期：2018.5

  The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis

  已经证明使用钴催化剂通过串联反应由异硫氰酸酯合成氰酰胺和四唑。在制备四唑的情况下，反应涉及加成/脱硫/亲核加成/电环化，而芳族氰胺是通过加成/脱硫由异硫氰酸酯构成的。廉价的硫酸钴被用于合成各种氰胺和四唑。另外，发现钴催化剂是以前没有报道的脱硫试剂。从起始前体以高产率到高产率获得了最终产物。
• Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions
  作者：Venkata Bhavanarushi Pendem、Ramana Tamminana、Madhavi Nannapaneni

  DOI：10.1007/s12039-021-02001-5

  日期：2022.3

  The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized

  铁介导的高效多组分方法已被证明可在温和的反应条件下从异硫氰酸酯合成取代的氰胺。随后的亲核加成和脱硫参与了该建议的合成方法。所有的反应都是快速、容易的，并且在室温下完成。各种底物很容易经历优化的反应条件，以提供其各自的目标产物，产率良好至极好。此外，我们已经确认在我们的实验反应过程中没有发现其他副产物。 图形概要 铁介导的高效多组分方法已被证明可在温和的反应条件下从异硫氰酸酯合成取代的氰胺。随后的亲核加成和脱硫参与了该建议的合成方法。
• One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives
  作者：Usharani Mandapati、Pavan Mandapati、Srinivasarao Pinapati、Ramana Tamminana、Rameshraju Rudraraju

  DOI：10.1080/00397911.2017.1402349

  日期：2018.3.4

  methodology for the synthesis of aryl/alkyl cyanamides from amines in one-pot four steps reaction using cheap, readily available and air stable copper source as catalyst under mild reaction conditions. We have also studied the application of cyanamides. In this connection, we could construct aryl tetrazolamine from cyanamides using click reaction GRAPHICAL ABSTRACT

  摘要 我们开发了一种方法，用于在温和的反应条件下，使用廉价、易得且空气稳定的铜源作为催化剂，通过一锅四步反应从胺合成芳基/烷基氰胺。我们还研究了氰胺的应用。在这方面，我们可以使用点击反应从氰胺中构建芳基四唑胺。
• The synthesis of arylcyanamides: a copper-catalyzed consecutive desulfurization and C–N cross-coupling strategy
  作者：S. N. Murthy Boddapati、Naresh Polam、Baby Ramana Mutchu、Hari Babu Bollikolla

  DOI：10.1039/c7nj03527f

  日期：——

  A one pot highly efficient and simple protocol for the construction of aromatic cyanamides from thioureaviadesulphurization/C–N cross coupling using a cheap, readily available and air stable copper source as a catalyst has been described.

  一种高效简便的一锅法协议用于从硫脲经过脱硫/碳氮交叉偶联构建芳香基氰胺，使用廉价、易得和空气稳定的铜源作为催化剂。
• Synthesis of Cyanamides from Isoselenocyanates Promoted by Recyclable Ionic Liquid-Supported (Diacetoxyiodo)Benzene
  作者：Xue Li、Yingyi Huang、Bin Gan、Zhisheng Mi、Yuanyuan Xie

  DOI：10.3184/174751915x14447479752475

  日期：2015.11

  One-pot synthesis of cyanamides from isoselenocyanates through deselenisation promoted by ionic liquid-supported hypervalent iodine(III) reagent 1-(4-diacetoxyiodobenzyl)-3-methylimidazolium tetrafluoroborate ([dibmim]⁺[BF₄]⁻) was developed. This approach provided a simple, mild and environmentally benign way to construct cyanamides in good yields. Moreover, powder Se and [dibmim]⁺[BF₄]⁻ could be easily recycled. It was the first example of [dibmim]⁺[BF₄]⁻ to be used as a deselenising agent.

  在离子液体支持的高价碘（III）试剂 1-（4-二乙酰氧基碘苄基）-3-甲基咪唑四氟硼酸盐（[dibmim]+[BF4]-）的促进下，通过脱硒法从异硒氰酸酯一步合成氰酰胺。这种方法提供了一种简单、温和且对环境无害的方法来构建氰酰胺，而且产率很高。此外，粉末 Se 和 [dibmim]+[BF4]- 易于回收。这是[dibmim]+[BF4]- 用作脱硒剂的第一个实例。