N-(p-tolyl)pyrrolidine-1-carbothioamide | 152974-58-8

• 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-tolyl)pyrrolidine-1-carbothioamide
• 英文别名: N-(4-methylphenyl)-1-pyrrolidinecarbothioamide；N-(4-methylphenyl)pyrrolidine-1-carbothioamide
• CAS: 152974-58-8
• 化学式: C₁₂H₁₆N₂S
• mdl: MFCD00125685
• 分子量: 220.338
• InChiKey: KCSNYJBZSAYVIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  47.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(p-tolyl)pyrrolidine-1-carbothioamide 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到6-methyl-2-(pyrrolidin-1-yl)benzo[d]thiazole
  参考文献：
  名称：

  N-碘代琥珀酰亚胺介导分子内氧化 C(sp2)-S 键形成用于合成 2-氨基苯并噻唑衍生物

  摘要：

  报道了一种使用N-碘代琥珀酰亚胺以芳基硫脲为原料制备 2-氨基苯并噻唑衍生物的极其有效的合成方法。该方案具有反应条件温和、反应时间短、C ( sp 2 )-S 键构建的无金属氧化条件等特点。

  DOI：

  10.1080/17415993.2021.1989436
• 作为产物：
  描述：

  4-甲苯基异腈 以 neat (no solvent) 为溶剂， 反应 6.0h， 生成 N-(p-tolyl)pyrrolidine-1-carbothioamide
  参考文献：
  名称：

  无催化剂和无溶剂条件下基于异氰化物的多组分反应，用于合成不对称硫脲

  摘要：

  通过芳族异氰酸酯，胺与1,2-二叔丁基二硫醚（DTBS）的顺序一锅三组分反应，开发了一种新的高效合成硫脲衍生物的方法，并在其中合成了27个不同的实例好到极好的产量。DTBS被认为是不同时使用催化剂和溶剂的有效硫替代物。该协议不使用任何过渡金属催化剂或特殊的实验装置。

  DOI：

  10.1016/j.tetlet.2016.11.082

文献信息

• Synthesis and Coordination Chemistry of 3,4-Ethylene-Bridged 1,1,2,5-Tetrasubstituted Biguanides
  作者：Maximilian Dehmel、Valentin Vass、Lukas Prock、Helmar Görls、Robert Kretschmer

  DOI：10.1021/acs.inorgchem.9b03093

  日期：2020.3.2

  The synthesis of 3,4-ethylene-bridged 1,1,2,5-tetrasubstituted biguanides is reported, which are accessible by three alternative routes. Exemplary molecular structures of the ligand and an observed side product have been elucidated by X-ray diffraction analysis. Mono- and dinuclear complexes of the biguanide in both its neutral and monoanionic forms were obtained, including examples of aluminum, copper

  据报道3，4-乙烯桥连的1,1,2,5-四取代双胍的合成，可通过三种替代途径进行。通过X射线衍射分析已经阐明了配体和观察到的副产物的示例性分子结构。获得了双胍的中性和单阴离子形式的单核和双核配合物，包括铝，铜，镁，钾，锡和锌的实例，表明其具有多种配位行为，如单晶X-射线衍射分析。
• A facile synthesis of N′-(p-toluenesulfonyl)-N-alkyl- and N,N-dialkylcyanoformamidines and 1,3-dialkyl-2-(p-toluenesulfonyl)guanidines
  作者：Keun Chan Oh、Hyunil Lee、Kyongtae Kim

  DOI：10.1016/s0040-4039(00)61246-7

  日期：1992.8

  lfonylimino)-5H-1,2,3-dithiazole (2) with primary and secondary amines in CH2Cl2 at room temperature gave N′-(p-toluenesulfonyl)-N-alkyl-and N,N-dialkylcyanoformamidines (3) (53–79% yields), respectively. Refluxing of 3 with secondary amines in CH2Cl2 gave 1,3-dialkyl-2-(p-toluenesulfonyl)guanidines (7) (40–99% yields), some of which (7a, 7c) were also directly obtained from the reactions of 2 with

  室温下，4-氯-5-（对甲苯磺酰氨基）-5H-1,2,3-二噻唑（2）与伯胺和仲胺在CH 2 Cl 2中的反应得到N'-（对甲苯磺酰基）-N -烷基-和N，N-二烷基氰基甲form （3）（53-79％产率）。将3与仲胺在CH 2 Cl 2中回流，得到1,3-二烷基-2-（对甲苯磺酰基）胍（7）（40-99％产率），其中一些（7a，7c）也可直接从2与相应胺的反应，无需使用溶剂。
• 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.
• Eosin Y Catalyzed Visible-Light-Promoted Aerobic Oxidative Cyclization of 2-Aminobenzothiazole
  作者：Vishal Srivastava、Pravin K. Singh、Praveen P. Singh

  DOI：10.5562/cca2632

  日期：——

  A mild and efficient one-pot visible light irradiated synthesis of 2-aminobenzothiazole 4(a-l) from arylisothiocyanate 1(a-l) and secondary amines 2 have been reported in presence of eosin Y as an organophotoredox catalyst at room temperature under aerobic condition. This synthesis includes application of air and visible light as inexpensive, readily available, high atom economy, non-toxic and sustainable regents.
• Chattree, N. S.; Chandel, M. S.; Sharma, T. C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 12, p. 1178 - 1180
  作者：Chattree, N. S.、Chandel, M. S.、Sharma, T. C.

  DOI：——

  日期：——