methyl 4-[2,2,2-trichloro-1-(4-chlorophenylsulfonylamino)ethyl]phenoxyacetate | 303014-09-7

• 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-(4-chlorophenylsulfonylamino)ethyl]phenoxyacetate
• 英文别名: Methyl [4-(2,2,2-trichloro-1-{[(4-chlorophenyl)sulfonyl]amino}ethyl)phenoxy]acetate；methyl 2-[4-[2,2,2-trichloro-1-[(4-chlorophenyl)sulfonylamino]ethyl]phenoxy]acetate
• CAS: 303014-09-7
• 化学式: C₁₇H₁₅Cl₄NO₅S
• 分子量: 487.188
• InChiKey: JIRGJIZZUWTNBV-UHFFFAOYSA-N

物化性质

• 沸点：
  570.5±60.0 °C(Predicted)
• 密度：
  1.500±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 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：
  90.1
• 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-(4-chlorophenylsulfonylamino)ethyl]phenoxyacetate 在 sodium hydroxide 作用下， 以98%的产率得到4-[2,2,2-trichloro-1-(4-chlorophenylsulfonylamino)ethyl]phenoxyacetic 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：

  N,N-dichloro-4-chlorobenzenesulfonamide 在 硫酸 作用下， 以 氯仿 为溶剂， 生成 methyl 4-[2,2,2-trichloro-1-(4-chlorophenylsulfonylamino)ethyl]phenoxyacetate
  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

• ——
  作者：E. V. Rudyakova、G. G. Levkovskaya、I. B. Rozentsveig、A. N. Mirskova、A. I. Albanov

  DOI：10.1023/a:1012385703287

  日期：——

  N-(2,2,2-Trichloroethylidene)- and N-(2,2,2-trichloroethyl)arenesulfonamides react with phenol, 2-chlorophenol, and 2-methylphenol in the presence of oleum or sulfuric acid to give the corresponding 4-(2,2,2-trichloro-1-arylsulfonylaminoethyl)phenols in good yields.
• Reactions of Aroxy- and Arylsulfanylacetic Acids and Their Esters with N-(2,2,2-Trichloro-1-hydroxyethyl)sulfonamides and -carboxamides
  作者：E. V. Rudyakova、G. G. Levkovskaya、I. B. Rozentsveig、A. N. Mirskova、A. I. Albanov

  DOI：10.1023/b:rujo.0000019739.80215.e2

  日期：2003.12

  C-Amidoalkylation of aroxy- and aryLsulfanylacetic acids and their methyl esters was effected by reaction with N-(2,2,2-trichloro-1-hydroxyethyl)sulfonamides and -carboxamides in the presence of methane- or trifluoromethanesulfonic acids as catalyst and solvent. The process is regioselective, and the substitution occurs at the para-position with respect to the heteroelement-containing group.