N-(5-(tert-butyl)-2-hydroxyphenyl)-4-methylbenzenesulfonamide | 136061-88-6

• 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-(5-(tert-butyl)-2-hydroxyphenyl)-4-methylbenzenesulfonamide
• 英文别名: N-(5-tert-butyl-2-hydroxyphenyl)-4-methylbenzenesulfonamide
• CAS: 136061-88-6
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: YRHCFNREFQTHAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(5-(tert-butyl)-2-hydroxyphenyl)-4-methylbenzenesulfonamide 在 叔丁基过氧化氢 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (5-(tert-butyl)benzo[d]oxazol-2-yl)(phenyl)methanone
  参考文献：
  名称：

  一锅的次碘酸盐催化的氧化环醚化方法的苯并恶唑。

  摘要：

  成功开发了一种实用的一锅式次碘酸盐催化氧化环化方法，用于合成α-酮基苯并恶唑衍生物。该操作简单的方案使用易于获得的起始原料，具有广泛的底物范围，且产率高。

  DOI：

  10.1039/c4cc02425g
• 作为产物：
  描述：

  O-(4-tert-butylphenyl)hydroxylamine 在 吡啶 、 六氟异丙醇 作用下， 反应 24.0h， 生成 N-(5-(tert-butyl)-2-hydroxyphenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  六氟异丙醇 (HFIP) 促进的 N-苯氧基磺酰胺重排，用于直接组装邻磺酰胺酚：实验和计算相结合的研究

  摘要：

  邻磺酰胺酚代表了药物和合成化学中一类有吸引力的结构基序。本文开发了一种有效的无金属重排反应，用于通过 HFIP 促进的分子内磺酰胺基团 1,3-迁移构建邻磺酰胺酚。该方案具有反应条件温和、官能团兼容性广、区域选择性好等特点。结合实验机理研究和详细的 DFT 计算，阐明了 HFIP 分子在促进该反应中的关键作用，并且推导出了独特的氢键网络来解释观察到的反应性。

  DOI：

  10.1016/j.tetlet.2021.153601

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.