2-[(4-iodophenyl)thio]acetic acid | 55631-91-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(4-iodophenyl)thio]acetic acid
• 英文别名: (4-iodo-phenylsulfanyl)-acetic acid；(4-Jod-phenylmercapto)-essigsaeure；2-(4-Iodophenyl)sulfanylacetic acid
• CAS: 55631-91-9
• 化学式: C₈H₇IO₂S
• 分子量: 294.113
• InChiKey: AZHLPMIPCYPCSP-UHFFFAOYSA-N

物化性质

• 沸点：
  382.7±27.0 °C(Predicted)
• 密度：
  1.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4-iodophenyl)thio]acetic acid 在 高氯酸 、 pyridinium chlorochromate 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 4-碘代苯-1-硫醇
  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：

  methyl [(4-aminophenyl)sulfanyl]acetate 在 盐酸 、 水 、 sodium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 2-[(4-iodophenyl)thio]acetic acid
  参考文献：
  名称：

  具有异羟肟酸结构的化合物及其制备方法和应用

  摘要：

  本发明提供了具有异羟肟酸结构的化合物及其制备方法和应用，属于化学药物领域。本发明提供的具有异羟肟酸结构的化合物，具有如式I、Ⅱ或Ⅲ所示的化学结构，通过将刺猬信号通路拮抗剂的药效基团与异羟肟酸片段拼合，增加化合物与HDAC中锌离子的螯合作用，在保持对刺猬信号通路拮抗作用的同时表现出较强的HDAC抑制作用。本发明提供的具有异羟肟酸结构的化合物，在浓度为10μM时，对HDAC的抑制率高达93.43％，在浓度为5μM时，下调刺猬信号通路转录因子Gli1的表达可达到‑87.10％，表现出对刺猬信号通路的活性有较强的抑制作用，在浓度为10μM时，对A549非小细胞肺癌细胞增殖的抑制率高达86.84％，抑制Jurkat白血病细胞的IC50值低至0.57μM。

  公开号：

  CN114292226B

文献信息

• Kinetics and Mechanism of the Oxidation of (Substituted Phenylthio)acetic Acids by Chloramine T
  作者：Chockalingam Srinivasan、Kasi Pitchumani

  DOI：10.1246/bcsj.55.289

  日期：1982.1

  phenylthio)acetic acids by chloramine T has been studied in alkaline medium (pH 10.06). A first-order dependence in chloramine T and (phenylthio)acetic acid and a near inverse first-order dependence in hydroxide ion has been observed. The oxidation rate considerably decreases with increase of pH. The reaction exhibits positive salt effect and added p-toluenesulfonamide increases the rate. The oxidation process

  已在碱性介质 (pH 10.06) 中研究了氯胺 T 氧化（苯硫基）乙酸和几种（对位取代的苯硫基）乙酸的动力学。已观察到氯胺 T 和（苯硫基）乙酸的一级相关性和氢氧根离子的近乎反向的一级相关性。氧化速率随着pH值的增加而显着降低。该反应显示出正盐效应，加入的对甲苯磺酰胺增加了速率。已显示氧化过程通过两条路径进行，主要路径涉及作为主要氧化物质的 N-氯-对甲苯磺酰胺，另一个涉及次氯酸根离子。对（对位取代的苯硫基）乙酸的研究表明，速率常数与 σ 常数具有极好的相关性。该反应在 308 K (r=0. 998，s=0.05，ρ±0.15 的置信限）。活化参数和等速温度已经确定。
• 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.
• NEW SYNTHESIS OF PHENYLTHIOGLYCOLIC ACIDS<i>via</i>RELATED TRIAZENE COMPOUNDS
  作者：Ali Disli、Yilmaz Yildirir

  DOI：10.1080/00304949809355295

  日期：1998.6
• CEPHALOSPORIN ANTIBIOTICS
  申请人：Microcide Pharmaceuticals, Inc.

  公开号：EP0754184A1

  公开（公告）日：1997-01-22
• US5604218A
  申请人：——

  公开号：US5604218A

  公开（公告）日：1997-02-18