4-((2-chlorophenyl)thio)aniline | 4726-27-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-((2-chlorophenyl)thio)aniline
• 英文别名: 4-[(2-Chlorophenyl)sulfanyl]aniline；4-(2-chlorophenyl)sulfanylaniline
• CAS: 4726-27-6
• 化学式: C₁₂H₁₀ClNS
• mdl: MFCD00094026
• 分子量: 235.737
• InChiKey: KAYQOCCQCIIXSP-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C
• 沸点：
  372.9±27.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((2-chlorophenyl)thio)aniline 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.08h， 生成 1-(4-((2-chlorophenyl)thio)phenyl)imidazolidin-2-one
  参考文献：
  名称：

  设计用于靶向秋水仙碱结合位点的取代 1-(4-(苯硫基)苯基)咪唑啉-2-酮、脲、硫脲和酰胺类似物和衍生物的基本原理、合成和生物学评价

  摘要：

  微管和抗微管剂在癌症化疗中很重要。事实上，微管对于在细胞分裂和细胞形态发生过程中形成有丝分裂纺锤体是必不可少的。在这项研究中，我们修改了名为 4-(2-oxoimidazolidin-1-yl)苯磺酸苯酯 (PIB-SOs) 的新型抗微管剂家族的结构部分，以评估取代 1) PIB 磺酸盐桥的效果-SOs 通过硫醚桥和 2) 咪唑啉-2-one 基团通过各种取代的脲部分、乙基硫脲或丁酰胺。为此，我们设计、制备和生物学评估了 42 种新的 PIB-SO 类似物和衍生物，即 1-(4-(苯硫基)苯基)咪唑啉-2-酮 (TPI)、1-(4-(苯硫基)苯基)脲 (TPU)、1-乙基-3-(4-(苯硫基)苯基)硫脲 (TPT) 和N-(4-(苯硫基)苯基)丁酰胺 (TPA)。最有效的衍生物对 HT-1080、HT-29、M21 和 MCF7 人类癌细胞系的抗增殖活性在纳摩尔到低微摩尔范围内。最有效的 TPU

  DOI：

  10.1016/j.molstruc.2022.132691
• 作为产物：
  描述：

  对硝基氯苯 在 乙醇 、 镍 作用下， 生成 4-((2-chlorophenyl)thio)aniline
  参考文献：
  名称：

  Some Basically Substituted Diaryl Sulfides and Sulfones

  摘要：

  DOI：

  10.1021/ja01200a069

文献信息

• Flavin/I2 catalyzed aerobic oxidative C H sulfenylation of anilines
  作者：Xinpeng Jiang、Zhifeng Shen、Cong Zheng、Liyun Fang、Keda Chen、Chuanming Yu

  DOI：10.1016/j.tetlet.2020.152141

  日期：2020.8

  A flavin/I2 catalyzed aerobic oxidative CH sulfenylation of anilines with thiols under mild reaction conditions is presented for the first time. This metal-free reaction provides an atom-economic pathway to prepare various aryl sulfides with outstanding functional group compatibility. Moreover, it consumes molecular oxygen as the only terminal oxidant and produces environmentally-friendly H2O as the

  首次提出在温和的反应条件下，黄素/ I 2催化苯胺与硫醇的好氧氧化C H亚磺酰化反应。这种无金属的反应为制备具有出色官能团相容性的各种芳基硫化物提供了一条原子经济途径。此外，它消耗分子氧作为唯一的终端氧化剂，并产生环保的H 2 O作为唯一的副产物。
• Iodine/DMSO-Promoted Selective Direct Arylthiation of Anilines with Thiols under Metal-Free Conditions
  作者：Wenqi Zhao、Feng Zhang、Guo-Jun Deng

  DOI：10.1021/acs.joc.0c02078

  日期：2021.1.1

  thiolation of unprotected anilines with thiols for the synthesis of sulfide anilines has been described. The combinational use of I2 and DMSO played an important role to realize this kind of transformation without the aid of a metal catalyst and strong oxidants. The reaction selectivity was well controlled to provide mono-, bis-, and trisubstituted diaryl sulfide derivatives. More importantly, iodination

  已经描述了碘促进的未保护苯胺与硫醇的发散硫醇化反应，用于合成硫化物苯胺。在不借助金属催化剂和强氧化剂的情况下，I 2和DMSO的组合使用对实现这种转化起了重要作用。很好地控制了反应的选择性，以提供单，双和三取代的二芳基硫醚衍生物。更重要的是，碘化和亚磺酰化可以同时发生，以提供有用的多官能化碘苯胺产物。该方法为在温和的反应条件下由C–H键构建C–S和C–I键提供了有效的方案。
• Structure-Based Design of Substituted Diphenyl Sulfones and Sulfoxides as Lipophilic Inhibitors of Thymidylate Synthase
  作者：Terence R. Jones、Stephen E. Webber、Michael D. Varney、M. Rami Reddy、Kathleen K. Lewis、Vinit Kathardekar、Hormoz Mazdiyasni、Judith Deal、Dzuy Nguyen、Katharine M. Welsh、Stephanie Webber、Amanda Johnston、David A. Matthews、Ward W. Smith、Cheryl A. Janson、Russell J. Bacquet、Eleanor F. Howland、Carol L. J. Booth、Steven M. Herrmann、Robert W. Ward、Jennifer White、Charlotte A. Bartlett、Cathy A. Morse

  DOI：10.1021/jm960613f

  日期：1997.2.1

  Six new diphenyl sulfoxide and five new diphenyl sulfones were designed, synthesized, and tested for their inhibition of human and Escherichia coli thymidylate synthase (TS) and of the growth of cells in tissue culture. The best sulfoxide inhibitor of human TS was 3-chloro-N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)-4-(phenylsulfinyl)-N-(prop-2-ynyl)-aniline (7c) that had a K-i of 27 nM. No sulfone improved on TS inhibition by the previously reported 4-(N-((3,4-dihydro-2-methyl-6-quinazolinyl)methyl)-N-prop-2-ynylamino)phenyl phenyl sulfone (K-i = 12 nM). Nevertheless, one sulfone, 4-((2-chlorophenyl)sulfonyl)-N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)-N-(prop-2-ynyl)analine, was selected, on the basis of its inhibition of both TS and cell growth, for antitumor testing; it gave a 61% increase in life span to mice bearing the thymidine kinase-deficient L5178Y (TK-) lymphoma. A crystal structure of N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)-4-((2-methylphenyl)sulfinyl)-N-(prop-2-ynyl)aniline complexed with E. coli TS was solved and revealed selective binding of one sulfoxide enantiomer. AMBER calculations showed that the enantioselection was due to asymmetric electrostatic effects at the mouth of the active site. In contrast, a similar crystal structure of the sulfoxide 7c, along with AMBER calculations, indicated that both enantiomers bound, but with different affinities. The side chain of Phe176 shifted in order to structurally accommodate the chlorine of the more weakly bound enantiomer.