Methyl {4-[2,2,2-trichloro-1-(phenylsulfonamido)ethyl]phenylsulfanyl}acetate

• 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: Methyl {4-[2,2,2-trichloro-1-(phenylsulfonamido)ethyl]phenylsulfanyl}acetate
• 英文别名: Methyl 2-[4-[1-(benzenesulfonamido)-2,2,2-trichloroethyl]phenyl]sulfanylacetate
• 化学式: C₁₇H₁₆Cl₃NO₄S₂
• 分子量: 468.809
• InChiKey: HPMHPBZTVQTUTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl {4-[2,2,2-trichloro-1-(phenylsulfonamido)ethyl]phenylsulfanyl}acetate 在 sodium hydroxide 作用下， 以95%的产率得到4-[2,2,2-trichloro-1-(phenylsulfonylamino)ethyl]phenylsulfanylacetic acid
  参考文献：
  名称：

  Synthesis of N-arylsulfonyl-2-aryl(hetaryl)aminoacetic acids

  摘要：

  Hydrolytic transformations of 4-[2,2,2-trichloro-1-(arylsulfonylamino)- and -(ethoxycarbonylamino)ethyl]phenyloxy(or sulfanyl)acetic acids under microwave irradiation in alkaline medium involve both trichloromethyl group and ester fragment to give N-arylsulfonyl-2-[4-carboxymethyloxy(or sulfanyl)phenyl]-2-aminoacetic acids in good yields. Hydrolysis of methyl 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl)acetates without microwave activation occurs only at the ester group with quantitative formation of 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl) acetic acids. N-[2,2,2-Trichloro-1-(1-naphthyl, 2-furyl, and 1-methylindol-3-yl)ethyl]-4-chlorobenzenesulfonamides in alkaline medium under microwave irradiation were converted in 10-15 min into the corresponding N-(4-chlorophenylsulfonyl)-2-aryl-2-aminoacetic acids in preparative yields.

  DOI：

  10.1134/s1070428006070098
• 作为产物：
  描述：

  二氯胺B 在 硫酸 作用下， 以 氯仿 为溶剂， 反应 11.0h， 生成 Methyl {4-[2,2,2-trichloro-1-(phenylsulfonamido)ethyl]phenylsulfanyl}acetate
  参考文献：
  名称：

  Levkovskaya; Krivonos; Rozentsveig, Russian Journal of Organic Chemistry, 2000, vol. 36, # 2, p. 240 - 244

  摘要：

  DOI：

文献信息

• Levkovskaya; Krivonos; Rozentsveig, Russian Journal of Organic Chemistry, 2000, vol. 36, # 2, p. 240 - 244
  作者：Levkovskaya、Krivonos、Rozentsveig、Mirskova、Albanov

  DOI：——

  日期：——
• Synthesis of N-arylsulfonyl-2-aryl(hetaryl)aminoacetic acids
  作者：E. V. Rudyakova、I. T. Evstaf’eva、I. B. Rozentsveig、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428006070098

  日期：2006.7

  Hydrolytic transformations of 4-[2,2,2-trichloro-1-(arylsulfonylamino)- and -(ethoxycarbonylamino)ethyl]phenyloxy(or sulfanyl)acetic acids under microwave irradiation in alkaline medium involve both trichloromethyl group and ester fragment to give N-arylsulfonyl-2-[4-carboxymethyloxy(or sulfanyl)phenyl]-2-aminoacetic acids in good yields. Hydrolysis of methyl 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl)acetates without microwave activation occurs only at the ester group with quantitative formation of 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl) acetic acids. N-[2,2,2-Trichloro-1-(1-naphthyl, 2-furyl, and 1-methylindol-3-yl)ethyl]-4-chlorobenzenesulfonamides in alkaline medium under microwave irradiation were converted in 10-15 min into the corresponding N-(4-chlorophenylsulfonyl)-2-aryl-2-aminoacetic acids in preparative yields.