N-(4-hydroxy-3,5-dimethylphenyl)benzenesulfonamide | 50994-42-8

• 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-(4-hydroxy-3,5-dimethylphenyl)benzenesulfonamide
• 英文别名: N-(3,5-dimethyl-4-hydroxyphenyl)benzenesulfonamide
• CAS: 50994-42-8
• 化学式: C₁₄H₁₅NO₃S
• 分子量: 277.344
• InChiKey: XVOYGDNHJYJIEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxy-3,5-dimethylphenyl)benzenesulfonamide 在 溴 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到3,5,6-tribromo-2,6-dimethyl-4-phenylsulfonylimino-2-cyclohexen-1-one
  参考文献：
  名称：

  Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters: V. Chlorination and bromination of N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring

  摘要：

  The direction of halogen addition to N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring is governed by the steric factors: the size and position of the substituent, the halogen volume, and the position of the substituent at the nitrogen. The first stage of halogenation of N-arylsulfonyl-4-aminophenols with two alkyl substituents in the phenylsulfonyl ring largely occurs as electrophilic substitution.

  DOI：

  10.1134/s1070428006050058
• 作为产物：
  描述：

  4-氨基-2,6-二甲基苯酚 、 苯磺酰氯 在 碳酸氢钠 作用下， 以 水 为溶剂， 以87%的产率得到N-(4-hydroxy-3,5-dimethylphenyl)benzenesulfonamide
  参考文献：
  名称：

  Avdeenko, Russian Journal of Organic Chemistry, 2000, vol. 36, # 4, p. 522 - 527

  摘要：

  DOI：

文献信息

• Avdeenko; Menafova; Zhukova, Russian Journal of Organic Chemistry, 1998, vol. 34, # 2, p. 210 - 220
  作者：Avdeenko、Menafova、Zhukova

  DOI：——

  日期：——
• Avdeenko, Russian Journal of Organic Chemistry, 2000, vol. 36, # 4, p. 522 - 527
  作者：Avdeenko

  DOI：——

  日期：——
• Toward Optimization of the Linker Substructure Common to Transthyretin Amyloidogenesis Inhibitors Using Biochemical and Structural Studies
  作者：Steven M. Johnson、Stephen Connelly、Ian A. Wilson、Jeffery W. Kelly

  DOI：10.1021/jm800435s

  日期：2008.10.23

  To develop potent and highly selective transthyretin (TTR) amyloidogenesis inhibitors, it is useful to systematically optimize the three substructural elements that compose a typical TTR kinetic stabilizer: the two aryl rings and the linker joining them. Herein, we evaluated 40 bisaryl molecules based on 10 unique linker substructures to determine how these linkages influence inhibitor potency and selectivity. These linkers connect one unsubstituted aromatic ring to either a 3,5-X 2 or a 3,5-X 2-4-OH phenyl substructure (X = Br or CH 3). Coconsideration of amyloid inhibition and ex vivo plasma TTR binding selectivity data reveal that direct connection of the two aryls or linkage through nonpolar E-olefin or -CH 2CH 2- substructures generates the most potent and selective TTR amyloidogenesis inhibitors exhibiting minimal undesirable binding to the thyroid hormone nuclear receptor or the COX-1 enzyme. Five high-resolution TTR.inhibitor crystal structures (1.4-1.8 A) provide insight into why such linkers afford inhibitors with greater potency and selectivity.
• Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters: V. Chlorination and bromination of N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring
  作者：A. P. Avdeenko、S. A. Konovalova

  DOI：10.1134/s1070428006050058

  日期：2006.5

  The direction of halogen addition to N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring is governed by the steric factors: the size and position of the substituent, the halogen volume, and the position of the substituent at the nitrogen. The first stage of halogenation of N-arylsulfonyl-4-aminophenols with two alkyl substituents in the phenylsulfonyl ring largely occurs as electrophilic substitution.