N-(2-aminophenyl)-1-phenylmethanesulfonamide | 182499-87-2

• 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: N-(2-aminophenyl)-1-phenylmethanesulfonamide
• 英文别名: N-(benzylsulfonyl)-o-phenylenediamine；o-(benzylsulfonylamino)aniline；2-(benzyl sulfonyl amino) aniline；2-(benzyl sulfonyl amino)-aniline；2-(benzyl sulfonyl amino)aniline
• CAS: 182499-87-2
• 化学式: C₁₃H₁₄N₂O₂S
• mdl: MFCD09050932
• 分子量: 262.332
• InChiKey: WMWPOLBAWLJWPR-UHFFFAOYSA-N

物化性质

• 沸点：
  452.6±55.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-aminophenyl)-1-phenylmethanesulfonamide 在 potassium carbonate 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 9.0h， 生成 4'-benzylsulfonyl-3,5-di-tert-butyl-3',4'-dihydro-3'-(p-nitrobenzoyl)spiro[2,5-cyclohexadiene-1,2'(1'H)-quinoxalin]-4-one
  参考文献：
  名称：

  摘要：

  A new procedure was proposed for synthesis of quinoxaline derivatives by N-alkylation of 2,6-di-tert-butyl-4-(o-R-sulfonylaminophenylimino)-2,5-cyclohexadienones and subsequent intramolecular spiro-cyclization. A necessary condition for the reaction to occur is a high mobility of hydrogen in the N-methylene group, which is activated by electron-acceptor aroyl or two ethoxycarbonyl groups.

  DOI：

  10.1023/a:1012399922502
• 作为产物：
  描述：

  邻苯二胺 、 苄磺酰氯 在 乙醇 作用下， 生成 N-(2-aminophenyl)-1-phenylmethanesulfonamide
  参考文献：
  名称：

  Phenyl urea antagonists of the IL-8 receptor

  摘要：

  本发明涉及式（I）的新化合物和这些化合物在治疗趋化因子介导的疾病方面的新用途，其中趋化因子结合到IL-8 a或b受体。式（1）的化合物由以下结构表示：其中，interalia，X是氧或硫；R是具有离子化氢和pKa小于10的任何功能基团；R1独立地选择自氢；卤素；硝基；氰基；C1-C10烷基；卤代C1-10烷基；C2-10烯基；C1-10烷氧基；卤代C1-10烷氧基；叠氮基；（CR8R8）qS（O）tR4；羟基；羟基取代的C1-4烷基；芳基；芳基C1-4烷基；芳基C2-10烯基；芳氧基；芳基C1-4烷氧基；杂芳基；杂芳基烷基；杂芳基C2-10烯基；杂芳基C1-4烷氧基；杂环，杂环C1-4烷基；杂环C1-4烷氧基；杂环C2-10烯基；q为0或具有值为1至10的整数；n为具有值为1至3的整数；m为具有值为1至3的整数；n为具有值为1至3的整数；Y是氢；卤素；硝基；氰基；卤代C1-10烷基；C1-10烷基；C2-10烯基；C1-10烷氧基；卤代C1-1-烷氧基；叠氮基；（CR8R8）qS（O）tR4，（CR8R8）qOR4；羟基；羟基取代的C1-4烷基；芳基；芳基C1-4烷基；芳氧基；芳基C1-4烷氧基；芳基C2-10烯基；杂芳基；杂芳基烷基；杂芳基C1-4烷氧基；杂芳基C2-10烯基；杂环，杂环C1-4烷基；杂环C2-10烯基；或其药学上可接受的盐。

  公开号：

  US06211373B1

文献信息

• IL-8 receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US05886044A1

  公开（公告）日：1999-03-23

  This invention relates to the novel use of phenyl ureas in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

  这项发明涉及苯基脲化合物在治疗由趋化因子白细胞介素-8（IL-8）介导的疾病状态中的新用途。
• <i>N</i>-{2-[(3,5-Di-<i>tert</i>-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino]phenyl}-<i>N</i>-(5,7-dinitroquinolin-8-yl)-1-phenylmethanesulfonamide: the nature of intramolecular shortened contacts
  作者：Oleg Ya. Borbulevych、Sergey V. Kurbatov、Sergey N. Borisenko、Lev P. Olekhnovich

  DOI：10.1107/s0108270104003439

  日期：2004.4.15

  The title compound, C36H35N5O7S, is found to exist in a nonspirocyclic (ring-opened) form in the crystal, although equilibrium of ring-opened and ring-closed forms ( or so-called ring - chain isomerization) is possible in solution. The 4-oxocyclohexa-2,5-diene ring has a flattened sofa conformation. The N...C intramolecular separation of the atoms which would be directly bonded in a ring-closed form is quite short [2.813 (5) Angstrom]. Topological analysis of charge density based on density-functional-theory calculations was used for consideration of shortened intramolecular contacts and indicates a strong attractive bonding interaction between these N and C atoms in the crystal structure.
• Tautomerism and Stereodynamics of Indophenols, Amidines, and Their Derivatives and Analogs: XVI. Synthesis of Tetrahydroquinoxalines Having Spiro-Fused Oxoindole and Cyclohepta[c]furan Fragments
  作者：S. V. Kurbatov、D. N. Kuznetsov、V. I. Simakov、V. A. Voronina、Yu. A. Zhdanov、L. P. Olekhnovich

  DOI：10.1023/b:rugc.0000039087.49416.5e

  日期：2004.5

  Alkylation of o-(N-sulfonylamino)phenylimino derivatives of indol-2-one and cyclohepta[c]furan with phenacyl bromides is accompanied by cyclization to previously unknown tetrahydroquinoxalines having spiro-fused oxoindole and cyclohepta[c]furan fragments. The structure of the latter includes a nitrogen-oxygen triangular system typical of most natural cytotoxic compounds.
• Tautomerism and Stereodynamics of Indophenols, Amidines, and Their Derivatives and Analogs: XV.¹Cyclization of N-Benzylidene-N'-R-sulfonyl-o-phenylenediamines to Tetrahydroquinoxalines
  作者：S. V. Kurbatov、D. N. Kuznetsov、V. I. Simakov、L. D. Popov、Yu. A. Zhdanov、L. P. Olekhnovich

  DOI：10.1023/b:rugc.0000007659.30597.5c

  日期：2003.8

  Alkylation of N-benzylidene-N'-R-sulfonyl-o-phenylenediamines with phenacyl bromides is accompanied by diastereoselective cyclization to afford tetrahydroquinoxaline derivatives. No cyclization occurs in the alkylation of the same compounds with p-nitrobenzyl bromide or chloroacetamide derivatives because of reduced reactivity of the N-methylene protons.
• US06005008
  申请人：——

  公开号：——

  公开（公告）日：——