<(2-Methoxyphenyl)thio>acetic acid | 18619-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: <(2-Methoxyphenyl)thio>acetic acid
• 英文别名: (2-methoxy-phenylsulfanyl)-acetic acid；(2-Methoxy-phenylmercapto)-essigsaeure；S-(2-Methoxy-phenyl)-thioglykolsaeure；(2-methoxyphenylthio)acetic acid；o-Methoxy-phenylmercapto-essigsaeure；2-((2-Methoxyphenyl)thio)acetic acid；2-(2-methoxyphenyl)sulfanylacetic acid
• CAS: 18619-21-1
• 化学式: C₉H₁₀O₃S
• mdl: MFCD01028311
• 分子量: 198.243
• InChiKey: UGPJOWVEIXPMSH-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  345.4±27.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  <(2-Methoxyphenyl)thio>acetic acid 在 高氯酸 、 pyridinium chlorochromate 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 2-甲氧基苯硫酚
  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：

  2-甲氧基苯硫酚 、 氯乙酸 在 sodium hydroxide 作用下， 生成 <(2-Methoxyphenyl)thio>acetic acid
  参考文献：
  名称：

  取代的（苯硫基）乙酸和（苯硒基）乙酸的酸解离常数

  摘要：

  据报道，制备了各种取代的（苯硫基）乙酸和（苯硒基）乙酸，其酸解离常数在20·0°和µ = 0·10 M（KNO 3）下测量。将该常数与相应的苯氧乙酸，β-苯基丙酸和苯甲酸的常数进行比较，以表明VI B族元素将苯环中取代基的电子效应传递至离解质子的能力。

  DOI：

  10.1039/j29680000588

文献信息

• [EN] FMS-LIKE TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE TYROSINE KINASE DE TYPE FMS
  申请人：3SM BIOTRON INC

  公开号：WO2019191896A1

  公开（公告）日：2019-10-10

  Provided are compounds of formula (I-1) -(I-4),which can be used as FLT3 inhibitors and for treatment and/or prevention of tumors.

  提供的化合物具有(I-1) -(I-4)的结构式，可用作FLT3抑制剂，用于肿瘤的治疗和/或预防。
• Kinetics and Mechanism of Oxidation of Ethyl Phenylthioacetates by Bromamine-B
  作者：Rajagopal Gurumurthy、Kulathu Iyer Sathiyanarayanan、Mannathusamy Gopalakrishnan

  DOI：10.1246/bcsj.65.1096

  日期：1992.4

  catalytic effect of mercury has been observed and the order with respect to Hg(II) is one. Electron-releasing substituents generally accelerate the rate while electron-withdrawing groups retard the rate. A good correlation is found to exist between log k2 and Hammett σ constants. Two mechanisms have been proposed, one in presence of Hg(II) and the other in the absence of Hg(II). In presence of Hg(II), rate

  在 50% (v/v) 乙醇水溶液中研究了溴胺-B（N-溴苯磺酰胺的钠盐）氧化几种取代的苯基硫代乙酸乙酯的动力学。已使用磷酸氢二钠和磷酸二氢钠缓冲液。该反应是总的二级反应，每个反应物都是一级反应。已经观察到汞的催化作用，并且相对于 Hg(II) 的顺序是一个。放电子取代基通常会加快速率，而吸电子基团会减慢速率。发现 log k2 和 Hammett σ 常数之间存在良好的相关性。已经提出了两种机制，一种是存在 Hg(II)，另一种是不存在 Hg(II)。存在 Hg(II) 时，速率 = k[C1][H2OBr]+ 且不存在 Hg(II)，
• RETRACTED: Design, synthesis, and biological evaluation of heterotetracyclic quinolinone derivatives as anticancer agents targeting topoisomerases
  作者：Jiann-Fong Lee、Ting-Yu Chang、Zheng-Fang Liu、Nian-Zhe Lee、Yen-Hsiu Yeh、Yi-Song Chen、Tsung-Chih Chen、Hao-Syun Chou、Tsai-Kun Li、Sung-Bau Lee、Mei-Hsiang Lin

  DOI：10.1016/j.ejmech.2020.112074

  日期：2020.3

  substitutions were synthesized and evaluated as topoisomerase (Topo) inhibitors. Six (8, 10, 12, 14, 19, and 26) of 23 compounds showed strong inhibitory activities against Topo-mediated DNA relaxation and proliferation of five human cell lines including breast (MDA-MB-231, MDA-MB-468 and MCF7), colorectal (HCT116) and non-small cell lung (H1299) cancers. Among these, compounds 14 and 26 exhibited full inhibitory

  合成了一系列具有各种取代基的硫代色素[2,3-c]喹啉-12-衍生物，并作为拓扑异构酶（Topo）抑制剂进行了评估。23种化合物中的6种（8、10、12、14、19和26）显示出对Topo介导的DNA松弛和包括乳腺在内的5种人类细胞系（MDA-MB-231，MDA-MB-468和MCF7），大肠癌（HCT116）和非小细胞肺癌（H1299）癌症。其中，化合物14和26对3μM的Topo I和1μM的TopoIIα表现出完全的抑制活性。经过26种处理的癌细胞累积了DNA损伤，被阻滞在G2 / M期。随着时间的流逝，细胞继续凋亡，这表现为DNA碎片化的细胞数量增加以及caspase-8和-9的裂解。相反，正常的乳腺上皮细胞对26的敏感性较低。
• Measurement of Gibbs energy of formation of LaGaO₃ using a composition-graded solid electrolyte
  作者：K. Thomas Jacob、Niladri Dasgupta、Helfried Näfe、Fritz Aldinger

  DOI：10.1557/jmr.2000.0405

  日期：2000.12

  A composition-graded solid electrolyte (LaF₃)_y · (CaF₂)_1-y was used for the measurement of the standard Gibbs energy of formation of LaGaO₃ from its component oxides. An equimolar mixture of CaO and CaF₂ was employed as the reference electrode. The composition of the working electrode depended on temperature. A three-phase mixture of LaGaO₃ + Ga₂O₃ + LaF₃ was used in the temperature range from 910 to 1010 K, while a mixture of LaGaO₃ + Ga₂O₃ + LaO_1-xF_1+2x was employed from 1010 to 1170 K. Both the reference and working electrodes were placed under pure oxygen gas. Because of the high activity of LaF₃ at the working electrode, there was significant diffusion of LaF₃ into CaF₂. The composition-graded electrolyte was designed to minimize the electrode–electrolyte interaction. The concentration of LaF₃ varied across the solid electrolyte; from y = 0 near the reference electrode to a maximum value y = 0.32 at the working electrode. For the correct interpretation of the electromotive force at T > 1010 K, it was necessary to use thermodynamic properties of the lanthanum oxyfluoride solid solution. The standard Gibbs energy of formation of LaGaO₃ from its component oxides according to the reaction, ½La₂O₃ (A-rare earth) + ½Ga₂O₃ (b) → LaGaO₃ (rhombohedral) can be represented by the equation: δGo _f,(ox) /J mol ^-1 = –46 230 + 7.75 T/K (±1500).

  使用成分分级固体电解质 (LaF3)y - (CaF2)1-y 测量了 LaGaO3 由其成分氧化物形成的标准吉布斯能。参比电极采用 CaO 和 的等摩尔混合物。工作电极的成分取决于温度。在 910 至 1010 K 的温度范围内使用的是 LaGaO3 + Ga2O3 + LaF3 的三相混合物，而在 1010 至 1170 K 的温度范围内使用的是 LaGaO3 + + LaO1-xF1+2x 的混合物。由于工作电极上的 LaF3 活性很高，LaF3 向 的扩散量很大。设计成分分级的电解质是为了尽量减少电极与电解质之间的相互作用。LaF3 的浓度在整个固体电解质中变化；从参比电极附近的 y = 0 到工作电极处的最大值 y = 0.32。为了正确解释 T > 1010 K 时的电动势，有必要使用氟化镧固溶体的热力学特性。按照 ½La2O3 (A-rare earth) + ½ (b) → LaGaO3 (rhombohedral) 的反应，LaGaO3 由其氧化物组分形成的标准吉布斯能可用公式表示：δGo f,(ox) /J mol -1 = -46 230 + 7.75 T/K (±1500) 。
• Metallation reactions. XX. regioselective metallation of (alkylthio)methoxybenzenes by superbases versus organolithium compounds
  作者：Salvatore Cabiddu、Claudia Fattuoni、Costantino Floris、Gioanna Gelli、Stefana Melis

  DOI：10.1016/s0040-4020(01)80413-0

  日期：1993.5

  (Alkylthio)methoxybenzenes have been metallated using two different metallating agents. The results show that sometimes superbases and butyllithium do not functionalize the same sites. Superbases monometallate the thiomethylic carbon of meta and para (methylthio)methoxybenzenes. The same substrates on the other hand are metallated by butyllithium in ortho to the methoxy group. One-step dimetallation

  （烷硫基）甲氧基苯已经使用两种不同的金属化剂金属化。结果表明，有时超碱和丁基锂不能官能化相同的位点。超碱单金属化间和对（甲硫基）甲氧基苯的硫代甲基碳。另一方面，相同的底物被丁基锂邻位甲氧基金属化。一步法与dimetallation要么超强碱进行，或者在thiomethylic碳和在芳基碳发生丁基锂邻于甲氧基。对位异构体（1c）与超碱的两个连续的一锅单金属化发生在硫代甲基碳和环状碳上甲氧基的邻位，按此顺序。用丁基锂类似的方法将两个邻位金属化成甲氧基。（乙硫基）衍生物（1d）的单金属化产生使用超碱或丁基锂在甲氧基上邻位取代的产物。该化合物的Dimetallation总是取代的氢邻到甲氧基和thiomethylenic氢。

表征谱图