N-(2,2,2-trichloroethyl-1-hydroxy)-2-thiophenesulfonamide | 730961-90-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(2,2,2-trichloroethyl-1-hydroxy)-2-thiophenesulfonamide
• 英文别名: N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide；N-(2,2,2-trichloro-1-hydroxyethyl)thiophene-2-sulfonamide
• CAS: 730961-90-7
• 化学式: C₆H₆Cl₃NO₃S₂
• 分子量: 310.61
• InChiKey: BSEULSYMRWHMCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2,2,2-trichloroethyl-1-hydroxy)-2-thiophenesulfonamide 在 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 N-(2-thienylsulfonyl)-2-(4-tolyl)glycine
  参考文献：
  名称：

  Synthesis and Properties of N-(2,2,2-Trichloroethyl)-2-thiophenesulfonamides

  摘要：

  Chlorination of 2-thiophenesulfonamide gave unstable N,N-dichloro-2-thiophenesulfonamide which was brought into reactions with 1,2-polyhaloethenes. The condensation of 2-thiophenesulfonamide with trichloroacetaldehyde afforded N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide which reacted with benzene, toluene, 2-chlorothiophene, and phenol to form the corresponding N-(1-aryl-2,2,2-trichloroethyl)-2-thiophenesulfonamides. Under more severe conditions, the latter were converted into 1,1-diaryl-2,2,2-trichloroethanes. The reaction of N-(2,2,2-trichloro-l-hydroxyethyl)-2-thiophenesulfonamide with substituted arenes, including phenol, was regioselective: only the corresponding para-substituted products were obtained. Hydrolysis of N-[2,2,2-trichloro-l-(4-tolyl)ethyl]-2-thiophenesulfonaniide yielded N-(2-thienylsulfonyl)-2(4-tolyl)glycine.

  DOI：

  10.1023/b:rujo.0000010224.50448.f5
• 作为产物：
  描述：

  2-噻吩磺酰胺 、 三氯乙醛 在 硫酸 作用下， 以98%的产率得到N-(2,2,2-trichloroethyl-1-hydroxy)-2-thiophenesulfonamide
  参考文献：
  名称：

  Synthesis and Properties of N-(2,2,2-Trichloroethyl)-2-thiophenesulfonamides

  摘要：

  Chlorination of 2-thiophenesulfonamide gave unstable N,N-dichloro-2-thiophenesulfonamide which was brought into reactions with 1,2-polyhaloethenes. The condensation of 2-thiophenesulfonamide with trichloroacetaldehyde afforded N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide which reacted with benzene, toluene, 2-chlorothiophene, and phenol to form the corresponding N-(1-aryl-2,2,2-trichloroethyl)-2-thiophenesulfonamides. Under more severe conditions, the latter were converted into 1,1-diaryl-2,2,2-trichloroethanes. The reaction of N-(2,2,2-trichloro-l-hydroxyethyl)-2-thiophenesulfonamide with substituted arenes, including phenol, was regioselective: only the corresponding para-substituted products were obtained. Hydrolysis of N-[2,2,2-trichloro-l-(4-tolyl)ethyl]-2-thiophenesulfonaniide yielded N-(2-thienylsulfonyl)-2(4-tolyl)glycine.

  DOI：

  10.1023/b:rujo.0000010224.50448.f5