(3-acetyl-phenylsulfanyl)-acetic acid | 163630-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-acetyl-phenylsulfanyl)-acetic acid
• 英文别名: (3-Acetyl-phenylmercapto)-essigsaeure；2-(3-Acetylphenyl)sulfanylacetic acid；2-(3-acetylphenyl)sulfanylacetic acid
• CAS: 163630-12-4
• 化学式: C₁₀H₁₀O₃S
• 分子量: 210.254
• InChiKey: DTYXJGQZMKOTMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-acetyl-phenylsulfanyl)-acetic acid 在 高氯酸 、 pyridinium chlorochromate 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 1-(3-巯基苯基)乙酮
  参考文献：
  名称：

  Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis

  摘要：

  Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acidmedium. The product of oxidation is the corresponding thiophenol. The rate data of meta- and para-substituted acids have been correlated well with sigma(I), sigma(R)degrees values and the meta-compounds correlate well with F, R values. The reaction constants are negative and of smaller magnitudes. Further, the ortho-substituted acids show a good correlation with triparametric equation involving Taft's sigma(I) and sigma(R)degrees and charton's steric parameter nu. There is no considerable steric contribution to the total orthosubstituent effect. Based on these observations, the mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed. (C) 1999 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1999)31:10<683::aid-jck1>3.0.co;2-9
• 作为产物：
  描述：

  巯基乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium carbonate 作用下， 生成 (3-acetyl-phenylsulfanyl)-acetic acid
  参考文献：
  名称：

  Ricci, Annali di Chimica, 1953, vol. 43, p. 323,328

  摘要：

  DOI：

文献信息

• Oxidative cleavage of S-arylmercaptoacetic acids by sodium perborate: Kinetic and correlation study
  作者：S. Kabilan、K. Pandiarajan、K. Krishnasamy、P. Sankar

  DOI：10.1002/kin.550270504

  日期：1995.5

  AbstractKinetics of oxidation of twenty six S‐arylmercaptoacetic acids (SAMA) (I) by sodium perborate (PB) have been studied in acid medium. The product of oxidation is the corresponding thiophenol. The rate data of meta‐and para‐substituted acids have been correlated with DSP equations. While the para‐compounds correlate well with σI and σR° values, the meta‐compounds correlate well with σI and σ values. The reaction constants are negative and of smaller magnitudes. Further, the ortho‐substituted acids show a good correlation with a triparametric equation involving Taft's σI and R° and Charton's steric parameter ν. There is a considerable steric contribution to the total ortho‐substituent effect. Based on these observations, mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed. © 1995 John Wiley & Sons, Inc.
• Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis
  作者：S. Kabilan、R. Girija、V. Rajagopal

  DOI：10.1002/(sici)1097-4601(1999)31:10<683::aid-jck1>3.0.co;2-9

  日期：——

  Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acidmedium. The product of oxidation is the corresponding thiophenol. The rate data of meta- and para-substituted acids have been correlated well with sigma(I), sigma(R)degrees values and the meta-compounds correlate well with F, R values. The reaction constants are negative and of smaller magnitudes. Further, the ortho-substituted acids show a good correlation with triparametric equation involving Taft's sigma(I) and sigma(R)degrees and charton's steric parameter nu. There is no considerable steric contribution to the total orthosubstituent effect. Based on these observations, the mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed. (C) 1999 John Wiley & Sons, Inc.
• Ricci, Annali di Chimica, 1953, vol. 43, p. 323,328
  作者：Ricci

  DOI：——

  日期：——