N-(2-hydroxy-5-nitrophenyl)-4-methylbenzenesulfonamide | 91956-17-1

• 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-hydroxy-5-nitrophenyl)-4-methylbenzenesulfonamide
• 英文别名: N-(2-hydroxy-5-nitrophenyl)-4-toluenesulfonamide；4-Nitro-2-(p-toluenesulfonamido)phenol；N-tosyl-2-amino 4-nitrophenol；toluene-4-sulfonic acid-(2-hydroxy-5-nitro-anilide)；Toluol-4-sulfonsaeure-(2-hydroxy-5-nitro-anilid)；p-Toluolsulfonsaeure-(5-nitro-2-oxy-anilid)；Benzenesulfonamide, N-(2-hydroxy-5-nitrophenyl)-4-methyl-
• CAS: 91956-17-1
• 化学式: C₁₃H₁₂N₂O₅S
• 分子量: 308.315
• InChiKey: RZTYHMOGMPYPFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  492.0±55.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-5-nitrophenyl)-4-methylbenzenesulfonamide 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 sodium hydride 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 100.0 ℃ 、344.73 kPa 条件下， 反应 101.25h， 生成 ethyl 2-[5,11-bis(2-ethoxy-2-oxoethyl)-15-nitro-14-(2,4,6-trinitroanilino)-2-oxa-5,8,11-triazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-8-yl]acetate
  参考文献：
  名称：

  A novel 12-membered triazaoxamacrocycle-N,N',N''-triacetic acid indicator for colorimetric determination of calcium

  摘要：

  The synthesis of a novel chromogenic triazaoxamacrocycle bearing three acetic acid groups and a 2,4,6-trinitroanilino chromophore, for generation of a spectrophotometric response, is described. As determined by potentiometric titration conducted in water, tetraionizable chromoionophore 4 forms a rather weak 1:1 complex with calcium (K(s) = 9.5 X 10(2) M-1) but exhibits very high selectivity for Ca2+ over Mg2+ at neutral pH. Cation responses at pH 7.0, 8.0, 9.0, and 10.0 are determined. The response of 4 to calcium is linear from 2 x 10(-5) to 1 x 10(-4) M Ca2+.

  DOI：

  10.1021/jo00069a034
• 作为产物：
  描述：

  5-Nitro-3-(4-toluenesulfonyl)-1,2,3-benzoxathiazole 2,2-dioxide 在 硫酸 作用下， 生成 N-(2-hydroxy-5-nitrophenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  一些芳香族环氨基磺酸盐的酸催化水解

  摘要：

  一些环状氨基磺酸盐的酸催化水解，X-3-(p-tolylsulfonyl)-1,2,3-benzoxathiazole 2,2-dioxides (1a, X = Me; 1b, X = H; 1c, X = Cl; 1d , X = NO 2 ) 在浓硫酸和高氯酸水溶液中进行了研究。过量酸度法的数据分析、活化参数、取代基、溶剂氘同位素效应和酸的催化效应顺序都与研究范围内的A-1机理一致。

  DOI：

  10.1080/10426500210670

文献信息

• Solvent-Controlled Pd(II)-Catalyzed Aerobic Chemoselective Intermolecular 1,2-Aminooxygenation and 1,2-Oxyamination of Conjugated Dienes for the Synthesis of Functionalized 1,4-Benzoxazines
  作者：Ke Wen、Zhengxing Wu、Banruo Huang、Zheng Ling、Ilya D. Gridnev、Wanbin Zhang

  DOI：10.1021/acs.orglett.8b00352

  日期：2018.3.16

  Pd(II)-catalyzed intermolecular 1,2-aminooxygenation and 1,2-oxyamination of conjugated dienes have been developed. The chemoselective preparation of a variety of 2-functionalized and 3-functionalized 1,4-benzoxazine derivatives was accomplished via the adjustment of a coordinating solvent. Oxygen was successfully used in this oxidative difunctionalization of alkenes. Good yields and selectivities

  已经开发了Pd（II）催化的共轭二烯的分子间1,2-氨基加氧和1,2-氧胺化。通过调节配位溶剂可以完成多种2官能化和3官能化的1,4-苯并恶嗪衍生物的化学选择性制备。氧气已成功用于烯烃的氧化双官能化。大多数产品都具有良好的收率和选择性。还从2，3-二取代的1，3-二烯获得带有螺线结构的产物。
• Synthesis of Benzoxazoles via an Amine-Catalyzed [4 + 1] Annulation
  作者：Aiguo Song、Xiaobei Chen、Xixi Song、Xinshuai Zhang、Shilei Zhang、Wei Wang

  DOI：10.1021/ol400988e

  日期：2013.5.17

  An unprecedented simple pyrrolidine catalyzed [4 + 1] annulation reaction of ynals with N-protected-2-aminophenols Is reported. The utilization of the unique property and reactivity of the C C triple bond in ynals leads to two consecutive conjugate addition reactions at the same beta-position with pyrrolidine via iminium activation. The powerful cascade process affords a new alternative approach to biologically and synthetically important benzoxazoles in high yields (83-95%).
• 1,2,3-Benzoxathiazole 2,2-dioxides: synthesis, mechanism of hydrolysis, and reactions with nucleophiles
  作者：Kenneth K. Andersen、Diana D. Bray、Sumalee Chumpradit、Michael E. Clark、Gregory J. Habgood、Colin D. Hubbard、Kathleen M. Young

  DOI：10.1021/jo00023a012

  日期：1991.11

  The rates of base-induced hydrolysis of some five-membered cyclic sulfamates, X-3-(p-tolylsulfonyl)-1,2,3-benzoxathiazole 2,2-dioxides (1a, X = H; 1b, X = 5-Me; 1c, X = 5-t-Bu; 1d, X = 5-Br; 1e, X = 5-Cl; 1f, X = 5-Ac; 1g, X = 5-NO2; 8a, X = 6-NO2) were measured in aqueous acetonitrile. The hydrolyses occurred with cleavage of the endocyclic N-SO2 bond. A Hammett plot using sigma-m values for 1a-g and sigma-p for 8a had rho = +2.20. Activation enthalpies and entropies were measured for 1a and for 3-methyl-1,2,3-benzoxathiazole 2,2-dioxide (10). Volumes of activation were determined for 1g and for 8a. The mechanistic profile for hydrolysis resembled that for the saponification of the analogous sultones and cyclic sulfates. These first examples of 1,2,3-benzoxathiazole 2,2-dioxides (1a-g, 8a) were prepared by treating N-(2-hydroxyphenyl)-p-toluenesulfonamides with sulfuryl chloride and triethylamine or by oxidizing the monoxide precursors using m-chloroperbenzoic acid. Treatment of 1a with potassium fluoride gave 1,2,3-benzoxathiazole 2,2-dioxide (9), which was methylated to give 10. Sulfamate 1a was treated with various nucleophilic reagents: phenyllithium, methyllithium, potassium fluoride, methylamine, tert-butylamine, and sodium methoxide. The first three attacked the tosyl sulfur atom and cleaved the exocyclic N-SO2 bond. The amines attacked the endocyclic sulfonyl sulfur atom and cleaved the endocyclic N-SO2 bond. Sodium methoxide attacked both sulfonyl groups.
• Synthesis and structure of 4,10-diaza-5'-nitro-2,3-dibenzo-12-crown-4
  作者：Richard A. Bartsch、Thomas W. Robison、Jan Krzykawski、N. Kent Dalley、Weiming Jiang、Dhimant H. Desai

  DOI：10.1021/jo00031a061

  日期：1992.2
• REACTIVITY OF NUCLEOPHILES TOWARDS X-3-(p-TOLYLSULFONYL)-1,2,3-BENZOXATHIAZOLE 2,2-DIOXIDES: KINETICS, ACTIVATION VOLUMES AND MECHANISM
  作者：Kenneth K. Andersen、Colin D. Hubbard、Achim Gerhard、Rudi Van Eldik、Martin G. Kociolek

  DOI：10.1002/(sici)1099-1395(199703)10:3<175::aid-poc887>3.0.co;2-2

  日期：1997.3