N-(p-Nitrophenyl)cyanothioformamide | 4953-70-2

• 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-(p-Nitrophenyl)cyanothioformamide
• 英文别名: N-(4-Nitrophenyl)cyanothioformamide；(4-nitrophenyl)cyanothioformamide；N-(4-Nitrophenyl)cyanthioformamid；1-cyano-N-(4-nitrophenyl)methanethioamide
• CAS: 4953-70-2
• 化学式: C₈H₅N₃O₂S
• 分子量: 207.213
• InChiKey: HSUNUMSCBJZIEL-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  353.4±44.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 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：
  114
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(p-Nitrophenyl)cyanothioformamide 在 copper(l) iodide 、 四丁基溴化铵 、 palladium dichloride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到6-硝基苯并[d]噻唑-2-甲腈
  参考文献：
  名称：

  Rapid and scalable assembly of firefly luciferase substrates

  摘要：

  提高对荧光素的获取将增强生物发光成像技术的应用。

  DOI：

  10.1039/c4ob02529f
• 作为产物：
  描述：

  4-Chlor-5-(4-nitrophenylimino)-5H-1,2,3-dithiazol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以32 %的产率得到N-(p-Nitrophenyl)cyanothioformamide
  参考文献：
  名称：

  通过 Pd 催化/Cu 辅助 CH 官能化/N-芳基氰基硫代甲酰胺的分子内 CS 键形成合成 2-氰基苯并噻唑。

  摘要：

  我们在此报告了一种涉及钯和铜的催化系统，以实现 N-芳基氰基硫代甲酰胺的环化和 2-氰基苯并噻唑的合成。CH 功能化/分子内 CS 键形成反应是在空气存在下使用 2.0 当量的无机添加剂 (KI) 实现的。在许多情况下，该反应导致以高收率区域选择性获得的唯一产物，允许合成范围广泛的取代 2-氰基苯并噻唑衍生物，为设计更复杂的杂环或分子标记系统提供有价值的构建模块。

  DOI：

  10.3390/molecules27238426

文献信息

• Reactions of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with stable phosphoranes: Novel preparation of dithiomethylenephosphoranes
  作者：Hyi-Seung Lee、Kyongtae Kim

  DOI：10.1016/0040-4039(95)02286-4

  日期：1996.2

  reactions of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with 2 equivalents of stable phosphoranes such as carboethoxymethylene-, acetylmethylene-, 4-chlorobenzoylmethylene-, and cyanomethylenetriphenylphosphoranes in the presence of pyridine in CH2Cl2 at room temperature gave a new type of the corresponding phosphoranes with aryliminocyanomethyldithiomethylene moiety as a major product.

  5-吡啶基-4-氯-5H-1,2,3-二噻唑与2当量的稳定phosphor烷在CH 2 Cl中在吡啶存在下的反应，如碳乙氧基亚甲基，乙酰基亚甲基，4-氯苯甲酰基亚甲基和氰基亚甲基三苯基膦2在室温下得到一种新型的相应的正膦，其主要成分是芳基氨基氰基甲基二硫亚甲基。
• Iodine-DMSO mediated conversion of <i>N</i>-arylcyanothioformamides to <i>N</i>-arylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles
  作者：Ziad Moussa、Zaher M. A. Judeh、Ahmed Alzamly、Saleh A. Ahmed、Harbi Tomah Al-Masri、Bassam Al-Hindawi、Faisal Rasool、Sara Saada

  DOI：10.1039/d2ra00049k

  日期：——

  substrates to access new luciferin analogs. The structures of all new products were elucidated by multinuclear NMR spectroscopy and high accuracy mass spectral analysis. Crystal-structure determination by means of single-crystal X-ray diffraction was carried out on (4-bromophenyl)carbamoyl cyanide, 5,6-dimethoxybenzo[d]thiazole-2-carbonitrile, 5-(benzyloxy)benzo[d]oxazole-2-carbonitrile, 4,7-dimetho

  氰基甲酰胺作为组装关键中间体和生物活性分子的有用成分无处不在。开发一种有效且简单的方法来处理这个主题是一个挑战。在此，我们证明了 I 2 -DMSO 氧化系统在从N制备N-芳基氰基甲酰胺中的有效性。-芳基氰基硫代甲酰胺。该合成方法具有条件温和、底物范围广、反应效率高等特点。此外，这种方法提供了一个很好的入口，可以专门提供 2-氰基苯并噻唑，它们是获得新荧光素类似物的有用底物。所有新产品的结构均通过多核核磁共振光谱和高精度质谱分析进行了阐明。用单晶X射线衍射对(4-溴苯基)氨基甲酰氰、5,6-二甲氧基苯并[ d ]噻唑-2-甲腈、5-(苄氧基)苯并[ d ]恶唑进行晶体结构测定-2-甲腈，4,7-二甲氧基苯并[ d]噻唑-2-甲腈和(5-碘-2,4-二甲氧基苯基)氨基甲酰氰，一种具有机理意义的关键中间体。
• English, Russell F.; Rakitin, Oleg A.; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1997, # 3, p. 201 - 205
  作者：English, Russell F.、Rakitin, Oleg A.、Rees, Charles W.、Vlasova, Olga G.

  DOI：——

  日期：——
• Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of D-luciferin
  作者：Marwaan Rylands、Anwar Jardine

  DOI：10.24820/ark.5550190.p011.420

  日期：——
• Reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles with primary and secondary alkylamines: novel synthesis of (arylimino)cyanomethyl alkylamino disulfides and their mechanisms of formation
  作者：Hyunil Lee、Kyongtae Kim

  DOI：10.1021/jo00077a017

  日期：1993.12

  Reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles with alkylamines such as isopropylamine, piperidine, pyrrolidine, and diethylamine in methylene chloride at room temperature gave (arylimino)cyanomethyl alkylamino disulfides (14-83%) along with N'-aryl-N-alkylcyanoformamidines (O-88%). The yields of the latter increase and those of the former decrease with the concentration of the amine. In addition, some of the latter compounds were independently synthesized by treatment of the former with cyclic amines such as piperidine, pyrrolidine, and morpholine in methylene chloride at room temperature (22-97%). The results indicate that the former compounds are involved as intermediates in the formation of the latter in these reactions. However, when [(p-nitrophenyl)-imino] cyanomethyl (pentane-1,5-diyl)amino disulfide was treated with sterically bulky amines such as tert-butyl- and diethylamines at reflux and room temperature, respectively, cyanoformamidines having a piperidine moiety rather than tert-butyl- and diethylamino groups were obtained as the only isolable products. Two pathways which involve initially either direct nucleophilic attack of alkylamines on the imino carbon or on the sulfur a to the amino group of (arylimino)cyanomethyl alkylamino disulfides are proposed to rationalize the results.