2-羟基-4-甲氧基苯甲酸乙酯 | 35031-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-4-甲氧基苯甲酸乙酯
• 英文名称: ethyl 2-hydroxy-4-methoxybenzoate
• 英文别名: 2-hydroxy-4-methoxy-benzoic acid ethyl ester；2-Hydroxy-4-methoxy-benzoesaeure-aethylester；4-Methylaether-β-resorcylsaeure-aethylester；2-Oxy-4-methoxy-benzoesaeureaethylester；4-Methoxy-salicylsaeureaethylester；2-Hydroxy-4-methoxybenzoesaeureaethylester
• CAS: 35031-00-6
• 化学式: C₁₀H₁₂O₄
• mdl: MFCD06204293
• 分子量: 196.203
• InChiKey: XTIRHTFASWVFJU-UHFFFAOYSA-N

物化性质

• 沸点：
  144 °C(Press: 17 Torr)
• 密度：
  1.180±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-4-甲氧基苯甲酸乙酯 在 sodium ethanolate 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-Methoxy-2-(5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazol-2-yl)phenol
  参考文献：
  名称：

  Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents

  摘要：

  A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 +/- 0.2, 30.0 +/- 1.2, 18.3 +/- 1.4 mu M, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 mu M, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 mu g/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.008
• 作为产物：
  描述：

  2,4-二羟基苯甲酸 在 盐酸 、 sodium hydroxide 作用下， 生成 2-羟基-4-甲氧基苯甲酸乙酯
  参考文献：
  名称：

  Gomberg; Johnson, Journal of the American Chemical Society, 1917, vol. 39, p. 1680

  摘要：

  DOI：

文献信息

• Synthesis, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents
  作者：Kai Liu、Xiang Lu、Hong-Jia Zhang、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2011.11.015

  日期：2012.1

  A series of 2-(benzylthio)-5-aryloxadiazole derivatives have been designed and synthesized, and their biological activities are also evaluated for EGFR inhibitory activity. Fourteen compounds among the twenty compounds are reported for the first time. Their chemical structures are characterized by 1H NMR, MS, and elemental analysis. Anti-proliferative and EGFR inhibition assay results have demonstrated

  已经设计和合成了一系列2-（苄硫基）-5-芳基恶二唑衍生物，并且还评估了它们的生物活性对EGFR的抑制活性。首次报道了二十种化合物中的十四种化合物。它们的化学结构通过1 H NMR，MS和元素分析进行表征。抗增殖和EGFR抑制测定的结果已经证实，化合物3e中示出了最有效的生物活性（IC 50  = 1.09μM为MCF-7和IC 50  = 1.51μM为EGFR）。已执行对接仿真以定位化合物3e进入EGFR活性位点以确定可能的结合模型，估计结合自由能值为-10.7 kcal / mol。在肿瘤生长抑制中具有有效抑制活性的化合物3e可能是有前途的抗肿瘤主导化合物，值得进一步研究。
• 13C NMR chemical shifts of the carbon atoms of the methoxymethyl group of di-ortho-substituted aromatic methoxymethyl ethers
  作者：Teodoro S. Kaufman、Robert D. Sindelar、Alex R. Jürgens

  DOI：10.1002/mrc.1260271213

  日期：1989.12

  Complete 13C spectral assignments of 28 aromatic methoxymethyl ethers bearing different substituents and substitution patterns were made. While meta-, para- or mono-ortho-substitution did not significantly affect the 13C resonances of the carbon atoms of the methoxymethyl group, di-ortho-substitution produced the deshielding of both carbons. This effect was more pronounced on the methylene carbon atom.

  完成了28种具有不同取代基和取代模式的芳香甲氧甲基醚的完整13C谱归属。在间位、对位或单一邻位取代的情况下，甲氧甲基碳原子的13C共振并未显著受到影响，但邻位双取代导致了两个碳原子的去屏蔽效应，其中甲叉基碳原子上的这一效应更为明显。
• Asymmetric Allylic C–H Alkylation via Palladium(II)/<i>cis</i>-ArSOX Catalysis
  作者：Wei Liu、Siraj Z. Ali、Stephen E. Ammann、M. Christina White

  DOI：10.1021/jacs.8b05668

  日期：2018.8.29

  asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles. The modular, tunable, and oxidatively stable ArSOX scaffold is key to the unprecedented broad scope and high enantioselectivity (37 examples, avg. > 90% ee). Pd(II)/ cis-ArSOX is unique in its ability to effect high reactivity and catalyst-controlled diastereoselectivity on the alkylation of aliphatic

  我们报告了 Pd(II)/顺式-芳基亚砜-恶唑啉 (cis-ArSOX) 催化剂的开发，用于末端烯烃的不对称 CH 烷基化与各种合成通用亲核试剂。模块化、可调且氧化稳定的 ArSOX 支架是前所未有的广泛范围和高对映选择性的关键（37 个例子，平均 > 90% ee）。Pd(II)/cis-ArSOX 的独特之处在于它能够对脂肪族烯烃的烷基化产生高反应性和催化剂控制的非对映选择性。我们预计这种新的手性配体类别将用于其他在氧化条件下运行的过渡金属催化过程。
• [EN] ANTI-CANCER COMPOUNDS<br/>[FR] COMPOSÉS ANTI-CANCEREUX
  申请人：UNIV TEXAS

  公开号：WO2015010032A1

  公开（公告）日：2015-01-22

  Provided are methods and compositions for the treatment of diseases such as cancer. In certain aspects, compounds which can inhibit Skp2 are provided. Specifically chromenone derivatives are disclosed that have the capability toward reducing differentiation of pluripotent, multipotent or totipotent cells and thus have therapeutic utility in the treatment of a proliferative disease such as cancer.

  提供了治疗癌症等疾病的方法和组合物。在某些方面，提供了可以抑制Skp2的化合物。具体地，披碱酮衍生物被揭示具有减少多能、多潜能或全能细胞分化的能力，因此在治疗癌症等增生性疾病中具有治疗效用。
• Synthesis of Phenanthrene Derivatives by Intramolecular Cyclization Utilizing the [1,2]-Phospha-Brook Rearrangement Catalyzed by a Brønsted Base
  作者：Azusa Kondoh、Takuma Aoki、Masahiro Terada

  DOI：10.1002/chem.201501377

  日期：2015.9.1

  The synthesis of functionalized phenanthrene derivatives was achieved by intramolecular cyclization utilizing the [1,2]‐phospha‐Brook rearrangement under Brønsted base catalysis. Treatment of biaryl compounds having an α‐ketoester moiety and an alkyne moiety at the 2 and 2′ positions, respectively, with diisopropyl phosphite in the presence of a catalytic amount of phosphazene base P2‐tBu provides

  功能化的菲衍生物的合成是通过在Brønsted碱催化下利用[1,2]-磷-布鲁克重排进行分子内环化来实现的。在催化量的磷腈碱P2 - t Bu存在下，用亚磷酸二异丙酯处理在2和2'位置分别具有α-酮酸酯部分和炔烃部分的联芳基化合物，可以得到9,10-二取代的菲衍生物。高产。该反应涉及通过乌珀隆过程生成酯烯酸酯，即将亚磷酸二异丙酯添加至酮部分，然后进行[1,2]-磷-布鲁克重排，将分子内添加至炔烃，以及[3] ，3]以连续方式重新排列烯丙基磷酸酯部分。