N-(3-Cyanophenyl)cyanamide | 154496-91-0

• 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: N-(3-Cyanophenyl)cyanamide
• 英文别名: (3-cyanophenyl)cyanamide
• CAS: 154496-91-0
• 化学式: C₈H₅N₃
• 分子量: 143.148
• InChiKey: JJDPEOGUMDYQBD-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：

  N-(3-Cyanophenyl)cyanamide 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-(3-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：

  溴化氰 、 间氨基苯甲腈 在 碳酸氢钠 作用下， 以 甲苯 为溶剂， 生成 N-(3-Cyanophenyl)cyanamide
  参考文献：
  名称：

  用于快速组装多取代 2-氨基咪唑和 2-亚氨基咪唑的碱控铜催化氰胺、三氟甲磺酸二芳基碘和炔丙胺的多组分级联反应

  摘要：

  分别以K 2 CO 3和吡啶为碱，建立了铜催化的氨腈、三氟甲磺酸二萘碘鎓和炔丙胺的三组分和四组分级联反应，用于快速构建多取代的 2-氨基咪唑和 2-亚氨基咪唑。铜有效地加速了每个反应步骤，构建了 3-4 个 C-N 键，具有出色的区域选择性和良好的产率。

  DOI：

  10.1039/d3nj01373a

文献信息

• Copper and In Situ-Generated Triflic Acid Relay-Promoted Four-Component Cascade Reaction for the Construction of Polysubstituted Cycloguanidines
  作者：Yiming Zhao、Run Yang、Canming Wu、Shihan Wang、Xinghua Liu、Jihui Li、Shuying Xu

  DOI：10.1021/acs.joc.3c00415

  日期：2023.7.7

  An unprecedented copper and in situ-generated triflic acid relay-promoted four-component cascade reaction of cyanamides, diaryliodonium triflates, propargylic amines, and H2O was established for rapid and concise construction of diverse five-membered cycloguanidines. Copper-catalyzed guanidination/intramolecular hydroamination and in situ-generated HOTf-accelerated hydration proceeded sequentially

  建立了前所未有的铜和原位生成的三氟甲磺酸中继促进的氰胺、二芳基碘鎓三氟甲磺酸盐、炔丙胺和H 2 O的四组分级联反应，用于快速、简洁地构建多种五元环胍。铜催化的胍基化/分子内氢胺化和原位生成的HOTf加速水合顺序进行，具有高水平的化学选择性和区域选择性，并且以高产率同时构建了6个新键。因此，二芳基碘鎓三氟甲磺酸盐不仅用作芳基化试剂，而且还用作内部酸促进剂，为高效利用二芳基碘鎓三氟甲磺酸盐建立了替代策略。
• US5266701A
  申请人：——

  公开号：US5266701A

  公开（公告）日：1993-11-30
• Novel and green protocol for the synthesis of 2-iminohydantoins
  作者：Vinod Kumar、Hemlata Rana、M.P. Kaushik

  DOI：10.1016/j.tetlet.2012.09.057

  日期：2012.11

  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.
• Base-controlled copper-catalyzed multi-component cascade reactions of cyanamides, diaryliodonium triflates and propargylamine for rapid assembly of polysubstituted 2-aminoimidazoles and 2-iminoimidazoles
  作者：Run Yang、Yiming Zhao、Shihan Wang、Canming Wu、Jihui Li、Shuying Xu

  DOI：10.1039/d3nj01373a

  日期：——

  Copper-catalyzed three-component and four-component cascade reactions of cyanamides, dirayliodonium triflates, and propargylamine were established for the rapid construction of polysubstituted 2-aminoimidazoles and 2-iminoimidazoles using K2CO3 and pyridine as the base, respectively. Each reaction step was efficiently accelerated by copper, and 3–4 C–N bonds were constructed with excellent regioselectivities

  分别以K 2 CO 3和吡啶为碱，建立了铜催化的氨腈、三氟甲磺酸二萘碘鎓和炔丙胺的三组分和四组分级联反应，用于快速构建多取代的 2-氨基咪唑和 2-亚氨基咪唑。铜有效地加速了每个反应步骤，构建了 3-4 个 C-N 键，具有出色的区域选择性和良好的产率。