2-羟基-4-甲基苯乙酸 | 38692-77-2

• 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-甲基苯乙酸
• 英文名称: 2-(2-hydroxy-4-methylphenyl)acetic acid
• CAS: 38692-77-2
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: WSFIDIJAAUEJLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-4-甲基苯乙酸 生成 6-methyl-2,3-dihydrobenzo[b]furan-2-one
  参考文献：
  名称：

  Aubert et al., Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 433,438

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基水杨酸 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 四丁基溴化铵 、 氢气 、 三溴化磷 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 、 水 、 苯 为溶剂， 反应 20.17h， 生成 2-羟基-4-甲基苯乙酸
  参考文献：
  名称：

  Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo

  摘要：

  In a search for compounds related to flavoneacetic acid with activity against solid tumors, a series of methyl-, methoxy-, chloro-, nitro-, and hydroxy-substituted xanthenone-4-acetic acids have been synthesized and evaluated against subcutaneously implanted colon adenocarcinoma 38 in vivo, using a short-term histology assay as a primary screening system. A major goal of this work was to identify compounds with similar profiles of activity to that of flavoneacetic acid but of higher potency. The level of activity of the compounds appeared to depend more on the nature of the substituent than its positioning, in the order Cl greater than Me, OMe greater than NO2, OH. However, the potency of the compounds was related much more to the position rather than the nature of the substitution, with 5-substituted compounds being clearly the most dose potent. 5-Methylxanthenone-4-acetic acid has a similar level of activity to that of flavoneacetic acid in the test systems employed but is more than 7-fold as dose potent.

  DOI：

  10.1021/jm00124a012

文献信息

• Synthesis and Absolute Configuration of Two Natural Phenolic Homobenzyl Esters
  作者：Murong Xu、Shijun Zhu、Zejun Xu、Yikang Wu、Po Gao

  DOI：10.1002/cjoc.201500315

  日期：2015.7

  natural phenolic homobenzyl esters, isolated from Phragmipedium calurum (an orchid) and Eupatorium fortunei TURCZ (a perennial herb in the Asteraceae family), respectively, were synthesized in enantiopure forms. By comparison of the optical rotations for the synthetic and the natural samples, the absolute configurations for the natural products were reliably assigned. The synthesis also enables establishment

  以对映纯的形式合成了两种最近鉴定出的天然酚类高苄基酯，分别从芦苇（兰花）和紫茎泽兰TURCZ（菊苣科的一种多年生草本植物）中分离出来。通过比较合成样品和天然样品的旋光度，可以可靠地指定天然产品的绝对构型。该合成还能够建立密切相关的天然高苄基醇的绝对构型，并首次提供了另外两种天然高纯苄基酯的完整的物理和光谱数据。
• Compounds having antitumor and antibacterial properties
  申请人：Cancer Research Campaign Technology Limited

  公开号：US05281620A1

  公开（公告）日：1994-01-25

  The novel class of xanthenone-4-acetic acids represented by the general formula (I) ##STR1## where R.sub.1 represents up to two of the groups lower alkyl, halogen, CF.sub.3, CN, NO.sub.2, NH.sub.2, CH.sub.2 COOH, OR.sub.2, OH, NHCOR.sub.2, NHSO.sub.2 R.sub.2, SR.sub.2, SO.sub.2 R.sub.2, CH.sub.2 CONHR.sub.2 or NHR.sub.2 (where R.sub.2 is lower alkyl optionally substituted with hydroxy, amino or methoxy functions), at any of the positions 1-8 which are available, R.sub.1 may also represent the substitution of an aza (--N.dbd.) group for one or two of the methine (--CH.dbd.) groups in the carbocyclic rings and two of R.sub.1 on any two available adjacent positions may also represent the grouping --CH.dbd.CH--CH.dbd.CH-- to form an additional fused benzene ring; and basic addition salts thereof, possess antitumour and antibacterial properties.

  通式（I）所代表的新型黄色素-4-乙酸类化合物，其中R.sub.1代表以下任意一个或两个基团：低碳链烷基，卤素，CF.sub.3，CN，NO.sub.2，NH.sub.2，CH.sub.2 COOH，OR.sub.2，OH，NHCOR.sub.2，NHSO.sub.2 R.sub.2，SR.sub.2，SO.sub.2 R.sub.2，CH.sub.2 CONHR.sub.2或NHR.sub.2（其中R.sub.2为低碳链烷基，可选地带有羟基，氨基或甲氧基功能），在可用的1-8位置中的任意位置。R.sub.1还可以代表将一个或两个亚胺（-N.dbd.）基团取代为碳环中的一个或两个甲烷（-CH.dbd.）基团，而在任意两个可用的相邻位置上的两个R.sub.1也可以代表群-CH.dbd.CH-CH.dbd.CH-以形成额外的融合苯环;以及其基本加成盐，具有抗肿瘤和抗菌性能。
• Substituted Acids for the Treatment of Respiratory Diseases
  申请人：Bonnert Victor Roger

  公开号：US20080114002A1

  公开（公告）日：2008-05-15

  The invention relates to substituted acids of formula (I), where T, W, X, Y, Z, R 1 and R 2 as defined in the claims, as useful pharmaceutical compounds for treating asthma and rhinitis, pharmaceutical compositions containing them, and a processes for their preparation.

  本发明涉及式（I）的取代酸，其中T，W，X，Y，Z，R1和R2如权利要求所定义，作为治疗哮喘和鼻炎的有用药物化合物，包含它们的制药组合物以及其制备方法。
• Ligand-Enabled C–H Hydroxylation with Aqueous H₂O₂ at Room Temperature
  作者：Zhen Li、Han Seul Park、Jennifer X. Qiao、Kap-Sun Yeung、Jin-Quan Yu

  DOI：10.1021/jacs.2c08332

  日期：2022.10.5

  carboxyl-pyridone (CarboxPyridone) ligand that enables room-temperature Pd-catalyzed C–H hydroxylation of a broad range of benzoic and phenylacetic acids with an industry-compatible oxidant, aqueous hydrogen peroxide (35% H2O2). The scalability of this methodology is demonstrated by a 1000 mmol scale reaction of ibuprofen (206 g) using only a 1 mol % Pd catalyst loading. The utility of this protocol is further

  随着过去十年中大量Pd(II)催化的天然底物C-H活化反应的发展，开发能够在安全实用的条件下使用绿色氧化剂的催化剂已成为一个日益重要的挑战。值得注意的是，Pd(II) 催化剂与可持续含水 H 2 O 2的相容性一直是包括瓦克型氧化在内的催化领域的长期挑战。我们在此报道了一种双功能双齿羧基吡啶酮 (CarboxPyridone) 配体，该配体能够使用工业兼容的氧化剂过氧化氢水溶液 (35% H 2 O)在室温下 Pd 催化的各种苯甲酸和苯乙酸的 C-H 羟基化反应。2）。仅使用 1 mol% Pd 催化剂负载的布洛芬 (206 g) 的 1000 mmol 规模反应证明了该方法的可扩展性。通过产品的衍生化以及从使用该方法制备的苯酚中间体合成多氟天然产物古美斯坦和紫檀烯，进一步说明了该协议的实用性。
• A method for producing adapalene gels
  申请人：Galderma Research & Development

  公开号：EP2065032A1

  公开（公告）日：2009-06-03

  The invention relates to a method for producing an adapalene aqueous gel, which method comprises preparing a gelling medium A by mixing water and propylene glycol and adding a gelling agent; preparing an adapalene medium B by dispersing adapalene in water, in the presence of a surfactant; adding the adapalene medium B to the gelling medium A ; and adjusting the pH to about 4.7-5.

  本发明涉及一种生产阿达帕林水凝胶的方法，该方法包括通过混合水和丙二醇并添加胶凝剂制备胶凝介质 A；在表面活性剂存在的情况下，通过将阿达帕林分散在水中制备阿达帕林介质 B；将阿达帕林介质 B 添加到胶凝介质 A 中；以及将 pH 值调节至约 4.7-5。