4-chloro-3-((5-amino-2-chlorophenyl)disulfanyl)aniline | 20201-05-2

• 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: 4-chloro-3-((5-amino-2-chlorophenyl)disulfanyl)aniline
• 英文别名: 1,1'-disulphanediylbis(2-chloro-5-nitrobenzene)；1,1'-disulfanediylbis(2-chloro-5-nitrobenzene)；bis(5-nitro-2-chlorophenyl) disulfide；bis-(2-chloro-5-nitro-phenyl)-disulfide；Bis-(2-chlor-5-nitro-phenyl)-disulfid；2-chloro-5-nitrophenyl disulfide；1-chloro-2-[(2-chloro-5-nitrophenyl)disulfanyl]-4-nitrobenzene
• CAS: 20201-05-2
• 化学式: C₁₂H₆Cl₂N₂O₄S₂
• 分子量: 377.229
• InChiKey: QQDYIOTXSJACKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-chloro-3-((5-amino-2-chlorophenyl)disulfanyl)aniline 在 sodium tetrahydroborate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 30.5h， 生成 N-(4-chloro-3-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-氯-5-硝基苯胺 在 氢碘酸 作用下， 生成 4-chloro-3-((5-amino-2-chlorophenyl)disulfanyl)aniline
  参考文献：
  名称：

  Frankovskii,Ch.S.; Katsnel'son,E.Z., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 478 - 481

  摘要：

  DOI：

文献信息

• N-ARYLAMIDINE-SUBSTITUTED TRIFLUOROETHYL SULFIDE DERIVATIVES AS ACARICIDES AND INSECTICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20140315898A1

  公开（公告）日：2014-10-23

  The present invention relates to novel N-arylamide-substituted trifluoroethyl sulfide derivatives of the formula (I) in which X 1 , X 2 , X 3 , X 4 , R 1 , R 2 , R 3 , n have the meanings given in the description—to their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation

  本发明涉及公式（I）中的新型N-芳酰胺取代三氟乙基硫醚衍生物，其中X1、X2、X3、X4、R1、R2、R3、n的含义如描述所示—它们作为杀螨剂和杀虫剂用于控制动物害虫，并涉及其制备的过程和中间体。
• ARYL SULFIDE DERIVATIVES AND ARYL SULFOXIDE DERIVATIVES AS ACARICIDES AND INSECTICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150344499A1

  公开（公告）日：2015-12-03

  The present invention relates to aryl sulphide and aryl sulphoxide derivatives, to their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation. The aryl sulphide and aryl sulphoxide derivatives have the general structure (I) in which the respective radicals have the meanings given in the description.

  本发明涉及芳基硫醚和芳基亚砜衍生物，其用作杀螨剂和杀虫剂，用于控制动物害虫，并涉及其制备的过程和中间体。芳基硫醚和芳基亚砜衍生物具有一般结构（I），其中各自的基团具有描述中给出的含义。
• The Reaction of Diaryl Disulfides with the Cyanide Ion
  作者：Kazuhiko Tanaka、Jun-ichi Hayami、Aritsune Kaji

  DOI：10.1246/bcsj.45.536

  日期：1972.2

  The reaction of symmetrical disulfides with the cyanide ion in various solvents has been investigated. The reaction modes may be summarized as follows: (1) Dialkyl disulfides and diaryl disulfides with electron-with-drawing substituents react with the cyanide ion in DMSO or DMF to give the corresponding monosulfides. (2) Diaryl disulfides with electron-donating substituents react with DMSO to yield

  研究了对称二硫化物与氰化物离子在各种溶剂中的反应。反应方式可概括如下： (1) 带有吸电子取代基的二烷基二硫化物和二芳基二硫化物在DMSO或DMF中与氰根离子反应生成相应的单硫化物。(2) 带有给电子取代基的二芳基二硫化物与 DMSO 反应生成芳基甲基硫化物。(3) 二芳基二硫化物被氰化物离子裂解成硫醇阴离子和芳基硫氰酸盐，然后与醇反应得到烷基芳基硫化物。
• Preparation of the first ortho-substituted pentafluorosulfanylbenzenes
  作者：Alexey M. Sipyagin、Colin P. Bateman、Ying-Teck Tan、Joseph S. Thrasher

  DOI：10.1016/s0022-1139(01)00514-0

  日期：2001.12

  The preparation of the first ortho-substituted pentafluorosulfanylbenzenes was achieved. Oxidative fluorination (AgF2) of a series of aromatic disulfides containing different substituents ortho to the disulfide moiety gave only one ortho-substituted SF5-benzene, namely 1-fluoro-4-nitro-2-pentafluorosulfanylbenzene. This compound has been transformed into a variety of other ortho-substituted SF5-benzenes

  实现了第一邻位取代的五氟硫烷基苯的制备。一系列在二硫键部分邻有不同取代基的芳族二硫键的氧化氟化作用（AgF 2）仅产生一个邻位取代的SF 5-苯，即1-氟-4-硝基-2-五氟硫基苯。通过亲核取代反应，该化合物已被转化为多种其他邻位取代的SF 5-苯。
• Synthesis of aryl perfluoroalkyl sulfides from aromatic disulfides
  作者：A. M. Sipyagin、V. S. Enshov、S. A. Kashtanov、V. A. Potemkin、J. S. Thrasher、A. Waterfeld

  DOI：10.1023/b:rucb.0000030820.47938.ab

  日期：2004.2

  diaryl disulfides occurs through the S—S bond cleavage to form dihalo-, halonitro-, and halodinitrophenyl perfluoroalkyl sulfides. The latter type of compounds was obtained for the first time. The main side process is the perfluoroalkylation of the aromatic ring.

  在二芳基二硫化物存在下，氙 (ii) 双（全氟烷烃羧酸盐）的热解通过 SS 键断裂发生，形成二卤代-、卤代硝基-和卤代二硝基苯基全氟烷基硫化物。后一类化合物是首次获得。主要的副过程是芳环的全氟烷基化。