4-((2-methylphenyl)thio)nitrobenzene | 6640-56-8

• 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-methylphenyl)thio)nitrobenzene
• 英文别名: 2-methyl-4'-nitrodiphenylsulfide；(4-nitrophenyl)(2-tolyl)sulfane；(o-tolyl)(4-nitrophenyl)sulfane；(4-nitro-phenyl)-o-tolyl sulfide；(4-Nitro-phenyl)-o-tolyl-sulfid；<4-Nitro-phenyl>--sulfid；1-Methyl-2-[(4-nitrophenyl)sulfanyl]benzene；1-methyl-2-(4-nitrophenyl)sulfanylbenzene
• CAS: 6640-56-8
• 化学式: C₁₃H₁₁NO₂S
• 分子量: 245.302
• InChiKey: PMJPVEVUFKWVNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((2-methylphenyl)thio)nitrobenzene 在 甲醇 、 镍 作用下， 生成 4-(o-tolylthio)aniline
  参考文献：
  名称：

  Haddow et al., Philosophical transactions of the Royal Society of London. Series A, Mathematical and physical sciences, 1948, vol. 241, p. 147,192

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-nitrophenylthio)morpholine 以25%的产率得到
  参考文献：
  名称：

  Sefirow N. S., Syk N. W., Beloglaskina E. K., Tjurin W. S., Isw. AN. Ser. khim, (1995) N 2, S 324-326

  摘要：

  DOI：

文献信息

• Copper-catalyzed Ullmann coupling under ligand- and additive-free conditions. Part 2: S-Arylation of thiols with aryl iodides
  作者：Pongchart Buranaprasertsuk、Joyce Wei Wei Chang、Warinthorn Chavasiri、Philip Wai Hong Chan

  DOI：10.1016/j.tetlet.2008.01.060

  日期：2008.3

  S-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides catalyzed by copper iodide under mild ligand- and additive-free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) is accomplished in good to excellent product yields (up to 96%).

  在温和的无配体和无添加剂条件下（n Bu 4 NBr，PhMe，NaOH，回流，22 h），将各种取代的芳基和脂肪族硫醇与碘化铜催化的芳基卤化物进行S-芳基化反应产品收率（高达96％）。
• [EN] SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF<br/>[FR] ACTIVATEURS À PETITES MOLÉCULES DE NICOTINAMIDE PHOSPHORIBOSYLTRANSFÉRASE (NAMPT) ET LEURS UTILISATIONS
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2018132372A1

  公开（公告）日：2018-07-19

  Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.

  本文提供了尼古丁酰胺磷酸核糖转移酶（NAMPT）的小分子激活剂，包括这些化合物的组合物，以及使用这些化合物和组合物的方法。
• Cerium catalyst promoted C–S cross-coupling: synthesis of thioethers, dapsone and RN-18 precursors
  作者：José M. da C. Tavares Junior、Caren D. G. da Silva、Beatriz F. dos Santos、Nicole S. Souza、Aline R. de Oliveira、Vicente L. Kupfer、Andrelson W. Rinaldi、Nelson L. C. Domingues

  DOI：10.1039/c9ob02171j

  日期：——

  In this work, we present a novel, efficient and green methodology for the synthesis of thioethers by the C–S cross-coupling reaction with the assistance of [Ce(L-Pro)2]2Ox as a heterogeneous catalyst in good to excellent yields. A scale-up of the protocol was explored using an unpublished methodology for the synthesis of a dapsone-precursor, which proved to be very effective over a short time. The

  在这项工作中，我们提出了一种新型的，高效的，绿色的方法，该方法通过[Ce（L -Pro）2 ] 2 Ox作为非均相催化剂，通过CS交叉偶联反应合成硫醚。产量。使用未公开的氨苯砜前体的合成方法探索了该方案的扩大规模，事实证明在短时间内非常有效。回收了催化剂[Ce（L -Pro）2 ] 2 Ox，它对再五个反应循环是有效的。
• Verfahren zur Herstellung von Nitro-diphenyl(thio)-ethern
  申请人：BAYER AG

  公开号：EP0304725A1

  公开（公告）日：1989-03-01

  Nitro-diphenyl(thio)ether, in denen die Nitrogruppe in ortho-oder para-Stellung zum Ether-Sauerstoff oder Ether-Schwefel steht, können aus Halogen-nitrobenzolen, in denen die Nitrogruppe in ortho- oder para-Stellung zum Halogen steht, und Alkali(thio)phenolaten in flüssigem Ammoniak hergestellt werden, wobei man die Reaktion unter Druck und bei einer Temperatur von -30°C bis +140°C durchgeführt und das Ammoniak nach Beendigung der Reaktion abtrennt.

  硝基二苯基（硫代）醚（其中硝基位于醚氧或醚硫的正对或对位）可由卤代硝基苯（其中硝基位于卤素的正对或对位）和碱（硫代）苯酚在液氨中制备，反应在加压和-30°C 至 +140°C的温度下进行，反应完成后分离氨。
• 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.