(2-chlorophenyl)(4-nitrophenyl)sulfane | 33667-99-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-chlorophenyl)(4-nitrophenyl)sulfane
• 英文别名: 1-Chloro-2-[(4-nitrophenyl)sulfanyl]benzene；1-chloro-2-(4-nitrophenyl)sulfanylbenzene
• CAS: 33667-99-1
• 化学式: C₁₂H₈ClNO₂S
• 分子量: 265.72
• InChiKey: RUVNVGIHOVENLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (2-chlorophenyl)(4-nitrophenyl)sulfane 在 双氧水 、 溶剂黄146 作用下， 生成 (2-Chlor-phenyl)-(4-nitro-phenyl)-sulfon
  参考文献：
  名称：

  Some Basically Substituted Diaryl Sulfides and Sulfones

  摘要：

  DOI：

  10.1021/ja01200a069
• 作为产物：
  描述：

  邻氯苯硫酚 、 对氟硝基苯 在 sodium hydride 作用下， 生成 (2-chlorophenyl)(4-nitrophenyl)sulfane
  参考文献：
  名称：

  Structure-Based Design of Substituted Diphenyl Sulfones and Sulfoxides as Lipophilic Inhibitors of Thymidylate Synthase

  摘要：

  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.

  DOI：

  10.1021/jm960613f

文献信息

• Synthesis of diaryl sulfides based on copper-doped OMS-2
  作者：Shao-Qiang Yu、Na Liu、Ming-Guo Liu、Long Wang

  DOI：10.1177/1747519820966985

  日期：2021.3

  We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance

  我们描述了一种使用 Cu-OMS-2 作为催化剂有效制备二芳基硫醚化合物的实用方案。Cu-OMS-2来源于用铜离子修饰的氧化锰八面体分子筛，催化取代苯硫酚和芳基卤化物的C-S偶联反应。该方案具有环境友好、操作简单、收率高、官能团耐受性好、Cu-OMS-2催化材料可多次循环利用等优点。
• 锰氧分子筛掺杂铜催化剂合成二芳基硫醚类化合物的方法
  申请人：三峡大学

  公开号：CN111978219B

  公开（公告）日：2022-05-06

  本发明涉及一种非均相锰氧八面体型分子筛掺杂铜(Cu‑OMS‑2)催化的二芳基硫醚类化合物的合成方法。其中，取代基R1为4‑甲基、2‑氯、3‑氯、4‑氯、4‑氟，R2为4‑氰基、4‑硝基、4‑甲氧基取代芳基中的任意一种。合成方法为以取代苯硫酚和芳基卤化物在锰氧八面体型分子筛(OMS‑2)掺杂铜配合物的催化下，于60～110℃下在二甲基亚砜溶剂中发生的C‑S偶联反应，经过滤、萃取和柱层析得到二芳基硫醚类化合物，该类化合物广泛存在于天然产物、药物和材料分子中，在许多领域都有着广泛的应用，是生物，医药，有机合成领域的重要合成中间体。
• 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。
• INHIBITORS OF LFA-1 BINDING TO ICAMs AND USES THEREOF
  申请人：ICOS CORPORATION

  公开号：EP1165504A2

  公开（公告）日：2002-01-02
• JP2002541141A
  申请人：——

  公开号：JP2002541141A

  公开（公告）日：2002-12-03