3-氯-4-硫代氰酰基苯胺 | 3226-46-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-氯-4-硫代氰酰基苯胺
• 英文名称: 3-chloro-4-thiocyanatoaniline
• 英文别名: 3-Chlor-4-thiocyanato-anilin；(4-amino-2-chlorophenyl) thiocyanate
• CAS: 3226-46-8
• 化学式: C₇H₅ClN₂S
• mdl: MFCD07613584
• 分子量: 184.649
• InChiKey: TUHUVPGYYIDKLW-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  319.1±32.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  75.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氯-4-硫代氰酰基苯胺 在 sodium tetrahydroborate 、 1,4-dithio-erythritol 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 N-(3-chloro-4-mercaptophenyl)picolinamide
  参考文献：
  名称：

  Synthesis and evaluation of N-(methylthiophenyl)picolinamide derivatives as PET radioligands for metabotropic glutamate receptor subtype 4

  摘要：

  In recent years, mGlu(4) has received great research attention because of the potential benefits of mGlu(4) activation in treating numerous brain disorders, such as Parkinson's disease (PD). A specific mGlu(4) PET radioligand could be an important tool in understanding the role of mGlu(4) in both healthy and disease conditions, and also for the development of new drugs. In this study, we synthesized four new N-(methylthiophenyl)picolinamide derivatives 11-14. Of these ligands, 11 and 14 showed high in vitro binding affinity for mGlu(4) with IC50 values of 3.4 nM and 3.1 nM, respectively, and suitable physicochemical parameters. Compound 11 also showed enhanced metabolic stability and good selectivity to other mGluRs. [C-11]11 and [C-11]14 were radiolabeled using the [C-11] methylation of the thiophenol precursors 20a and 20c with [C-11]CH3I in 19.0% and 34.8% radiochemical yields (RCY), and their specific activities at the end of synthesis (EOS) were 496 +/- 138 GBq/mu mol (n = 6) and 463 +/- 263 GBq/mu mol (n = 4), respectively. The PET studies showed that [C-11]11 accumulated fast into the brain and had higher uptake, slower washout and 25% better contrast than [C-11]2, indicating improved imaging characteristics as PET radiotracer for mGlu(4) compared to [C-11]2. Therefore, [C-11]11 will be a useful radioligand to investigate mGlu(4) in different biological applications. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.015
• 作为产物：
  描述：

  2-chloro-4-nitro-phenyl thiocyanate 在 盐酸 、 tin(ll) chloride 作用下， 生成 3-氯-4-硫代氰酰基苯胺
  参考文献：
  名称：

  Takahashi et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 649,651

  摘要：

  DOI：

文献信息

• Synthesis of new antimicrobials. III. Synthesis of chlorine-substituted 4-thiocyanatoaniline and 2-amino-6-chlorobenzothiazole derivatives.
  作者：TAKAHIRO YABUUCHI、MASAKATU HISAKI、RYUICHI KIMURA

  DOI：10.1248/cpb.23.659

  日期：——

  In order to examine their antimicrobial activity, new N-derivatives of chlorine-substituted 4-thiocyanatoanilines (A) and 2-amino-6-chlorobenzothiazole (B) were prepared by the reaction of compound A or B with haloacetyl halides, alkyl chloroformates, phenoxyacetyl chlorides, phenyl isocyanates, or arylaldehydes.

  为了检验它们的抗菌活性，合成了氯取代的4-硫氰基苯胺（A）和2-氨基-6-氯苯噻唑（B）的新的N-衍生物，这些衍生物是通过化合物A或B与卤乙酰卤、烷基氯甲酸酯、苯氧乙酰氯、苯基异氰酸酯或芳醛反应得到的。
• Visible light thiocyanation of <i>N</i>-bearing aromatic and heteroaromatic compounds using Ag/TiO₂ nanotube photocatalyst
  作者：Mona Hosseini-Sarvari、Zeinab Hosseinpour、Mehdi Koohgard

  DOI：10.1039/c8nj03128b

  日期：——

  nanotubes (Ag/TNT) were synthesized via simple hydrothermal process, and this photocatalyst was successfully exploited in thiocyanation reactions at room temperature under visible light irradiation. Four classes of important heterocyclic compounds including indole, aniline, pyrrole and 2-amino thiazole derivatives via Ag/TNT treated with ammonium thiocyanate formed the corresponding thiocyano compounds

  本研究通过简单的水热法合成了Ag / TiO 2纳米管（Ag / TNT），并在室温下可见光照射下成功地将该光催化剂用于硫氰化反应。四类重要的杂环化合物，包括吲哚，苯胺，吡咯和2-氨基噻唑衍生物通过用硫氰酸铵处理的Ag / TNT以中等至极好的收率形成了相应的硫氰基化合物。Ag纳米颗粒（主要沉积在TNT的表面）对包含硫原子的吸收物种的等离子特性和催化性能是反应进行的关键因素。首次报道的这种有效，简单和通用的方案在可见光下提供了苯胺，吡咯和2-氨基噻唑衍生物的硫氰化反应。通过应用空气分子氧作为低成本和环境友好的末端氧化剂，反应通过自由基途径进行。
• ARS–TiO₂ photocatalyzed direct functionalization of sp2 C–H bonds toward thiocyanation and cyclization reactions under visible light
  作者：Mehdi Koohgard、Zeinab Hosseinpour、Abdollah Masoudi Sarvestani、Mona Hosseini-Sarvari

  DOI：10.1039/c9cy02268f

  日期：——

  the visible light spectrum. The synergic effect of ARS and TiO2 in the photocatalyst system has catalyzed direct C–H functionalization of sp2 C–H bonds toward thiocyanation and cyclization reactions. Several aromatic and heteroaromatic scaffolds (2-phenylamino-thiazole, phenol, aniline, indole and pyrrole derivatives) were treated with the thiocyanate anion at room temperature. Herein, the first report

  通过在室温下在黑暗中搅拌ARS和TiO 2的混合物的简单方法，制备了ARS-TiO 2光催化剂，以将二氧化钛的光催化响应扩展到可见光谱。ARS和TiO 2在光催化剂体系中的协同作用已经催化了sp2 C-H键的直接C-H功能化，从而实现了硫氰化和环化反应。在室温下，用硫氰酸根阴离子处理了几种芳族和杂芳族支架（2-苯基氨基噻唑，苯酚，苯胺，吲哚和吡咯衍生物）。在此，首次报道了在可见光下苯酚的硫氰化和2-氨基苯并噻唑衍生物的合成。
• 3'-Chloro-4'- thiocyanatohydrocinnamanilide
  申请人：Morton-Norwich Products, Inc.

  公开号：US03997583A1

  公开（公告）日：1976-12-14

  3'-Chloro-4'-thiocyanatohydrocinnamanilide is an effective antibacterial agent.

  3'-氯-4'-硫氰酸盐羟肉桂酰胺是一种有效的抗菌剂。
• An efficient synthesis of 4-Thiocyanato anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H2O
  作者：Reuben Dass、Justin D. Singleton、Matt A. Peterson

  DOI：10.1016/j.tetlet.2022.153809

  日期：2022.5

  substitution. 3-Substituted, 3,5- or 2,6-disubstituted anilines and substituted phenols were also well tolerated. 4-Substituted anilines gave the corresponding 2-aminobenzothiazole products, whereas 4-, 5-, 6-, or 7-substituted indoles were not reactive. Regioselective thiocyanation of 2-quinoline, 3-amino-1-methylpyrazole, 2-amino-4-phenylthiazole, and 2-phenylimidazo[1,2-a] pyridine was achieved in

  在 70 °C 下，在 DMSO:H 2 O (9:1)中用苄基三甲基二氯碘酸铵（1.2 equiv）和硫氰酸铵（1.2 equiv）处理各种 2(3)-单取代苯胺，得到相应的 4-硫氰酸根- 2(3)-取代的苯胺具有出色的分离产率（60–99%；所有苯胺的平均产率 = 90%）。该反应适用于具有 2-卤代、2-烷氧基、2-芳氧基、2-烷基、2-二烷基氨基、2- N-磺酰基氨基、2-炔基-1-基、2-氰基、2-酰基、2-磺酰基和2-杂芳基取代。3-取代、3,5-或2,6-二取代苯胺和取代苯酚也具有良好的耐受性。4-取代的苯胺产生相应的2-氨基苯并噻唑产物，而4-、5-、6-或7-取代的吲哚不反应。2-喹啉、3-氨基-1-甲基吡唑、2-氨基-4-苯基噻唑和2-苯基咪唑并[1,2-a]吡啶的区域选择性硫氰化产率为93-99%，从而证明了广泛的底物这种硫氰化反应的范围。