4-羟基-3-甲基苯甲酸乙酯 | 55211-85-3

• 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: 4-羟基-3-甲基苯甲酸乙酯
• 英文名称: ethyl 2-hydroxy-3-methylbenzoate
• 英文别名: ethyl 3-methylsalicylate
• CAS: 55211-85-3
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD06204663
• 分子量: 180.203
• InChiKey: NSRLIMVWJNHWJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918290000

反应信息

• 作为反应物：
  描述：

  4-羟基-3-甲基苯甲酸乙酯 在 ammonium hydroxide 作用下， 生成 甲酚酰胺
  参考文献：
  名称：

  Mameli, Gazzetta Chimica Italiana, 1926, vol. 56, p. 764

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基水杨酸 在 五氯化磷 、 Petroleum ether 作用下， 生成 4-羟基-3-甲基苯甲酸乙酯
  参考文献：
  名称：

  Anschuetz,R.; Schroeder; Weber, Justus Liebigs Annalen der Chemie, 1906, vol. 346, p. 342

  摘要：

  DOI：

文献信息

• Synthesis and Cytotoxic Evaluation of 3-Methylidenechroman-4-ones
  作者：Jacek Kędzia、Tomasz Bartosik、Joanna Drogosz、Anna Janecka、Urszula Krajewska、Tomasz Janecki

  DOI：10.3390/molecules24101868

  日期：——

  Horner–Wadsworth–Emmons reagents giving 2-substituted 3-methylidenechroman-4-ones, which were then tested for their possible cytotoxic activity against two leukemia cell lines, HL-60 and NALM-6, and against MCF-7 breast cancer cell line. All new compounds (14a–o) were highly cytotoxic for the leukemic cells and showed a moderate or weak effect on MCF-7 cells. Analog 14d exhibited the highest growth inhibitory

  在寻找新的抗癌剂的过程中，使用 Horner-Wadsworth-Emmons 方法合成了一个不同取代的 3-methylidenechroman-4-ones 库。甲基膦酸二乙酯与选定的水杨酸乙酯的酰化提供了 3-二乙氧基磷酰基色烯-4-酮，接下来将其用作与各种格氏试剂反应的迈克尔受体。加合物以反式和顺式非对映异构体以及少量烯醇形式的混合物形式获得。通过NMR分析确定了它们的相对构型和优选构象。结果证明，这些加合物是有效的 Horner-Wadsworth-Emmons 试剂，可产生 2-取代的 3-methylidenechroman-4-ones，然后测试它们对两种白血病细胞系 HL-60 和 NALM-6 的可能的细胞毒活性，以及​​对MCF-7 乳腺癌细胞系。所有新化合物 (14a-o) 对白血病细胞具有高度细胞毒性，对 MCF-7 细胞显示出中等或微弱的作用。类似物 14d 对
• Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds
  作者：Toshinori Miyagi、Sho Okada、Naoya Tada、Masahiro Sugihara、Natsuko Kagawa、Tetsuhiko Takabatake、Masahiro Toyota

  DOI：10.1016/j.tetlet.2019.05.041

  日期：2019.6

  A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and

  首次开发了钯催化的取代的2-羟基苯甲酸酯和取代的环己酮的正交合成。使用催化的Pd（OAc）2和Cu（OAc）2的组合，从无环不饱和1,3-羰基化合物获得取代的2-羟基苯甲酸酯。另一方面，取代的环己酮是通过催化的Pd（OAc）2和氯化氢由相似的底物制得的。每种转化都是干净的，易于后处理，可提供所需的高纯度化合物，且无需柱色谱法纯化。
• Synthesis, pharmacophore modeling and in vitro activity of 10,11-dihydrodibenzo[b,f]oxepine-4-carboxamide derivatives as novel and potent antagonists of the prostaglandin EP4 receptor
  作者：Luigi Piero Stasi、Kanji Bhimani、Manuela Borriello、Luca Canciani、Gianfranco Caselli、Fabrizio Colace、Cristian Ferioli、Mehul Kaswala、Laura Mennuni、Tiziana Piepoli、Sabrina Pucci、Matteo Salvi、Vikas Shirsath、Tiziano Zanelli、Silvia Zerbi

  DOI：10.1016/j.bmcl.2011.08.102

  日期：2011.11

  The construction of a EP4 antagonists pharmacophore model and the discovery of a highly potent oxepinic series of EP4 antagonists is discussed. Compound 1a exhibits an excellent selectivity profile toward EP2 receptor subtype and low cytochrome P450 inhibition potential.

  讨论了EP 4拮抗剂药效基团模型的构建以及高效的环氧哌啶系列EP 4拮抗剂的发现。化合物1a对EP 2受体亚型表现出出色的选择性，并具有低的细胞色素P450抑制潜能。
• Relationship Between the structure of Newly Synthesized derivatives of 1,3,4-oxadiazole Containing 2-Methylphenol and their Antioxidant and Antibacterial Activities
  作者：Shaimaa Abed Saoud、Khalid Fahad Ali、Raied Mustafa Shakir

  DOI：10.13005/ojc/330423

  日期：2017.8.28

  1,3,4-oxadiazole-5-thion ring (2) successfully formed at position six of 2-methylphenol and five of their thioalkyl (3a-e). Furthermore 6-(5-(Aryl)-1,3,4-oxadiazol-2-yl)-2-methylphenol (5a-i) were formed at position six by two method. The first method was from cyclization their corresponding hydrazones (4a-e) of 2-hydroxy-3-methylbenzohydrazide (1) using bromine in glacial acetic acid. The second method was from cyclization the hydrazide with aryl carboxylic acid in the presence of phosphorusoxy chloride. The newly synthesized compounds were characterized from their IR, NMR and mass spectra. The antioxidant properties of these compounds were screened by 2,2-Diphenyl-1-picrylhydrazide (DPPH) and ferric reducing antioxidant power (FRAP) assays. Compound (4d) and (5h) exhibited significant antioxidant properties in both assays, compared to ascorbic acid, while compound (4e) exhibited slightly less antioxidant properties than ascorbic acid. Antibacterial activity was tested for the twenty one compounds against eight microorganisms (gram negative and gram positive). Compound (4d) and (5d) exhibited significant antibacterial activities compared to Amoxicillin and Kanamycin as antibiotic standards.

  1,3,4-噁二唑-5-硫环（2）成功地在2-甲基苯酚的第六位和五种其硫烷基衍生物（3a-e）中形成。此外，通过两种方法在第六位合成了6-(5-(芳基)-1,3,4-噁二唑-2-基)-2-甲基苯酚（5a-i）。第一种方法是使用冰醋酸中的溴化物对2-羟基-3-甲基苯肼（1）的相应肼化合物（4a-e）进行环化。第二种方法是将肼与芳香酸在磷氧化氯的存在下进行环化。新合成的化合物通过其红外光谱（IR）、核磁共振（NMR）和质谱（MS）进行表征。这些化合物的抗氧化性能通过2,2-二苯基-1-皮克里尔肼（DPPH）和铁还原抗氧化能力（FRAP）测定进行筛选。与抗坏血酸相比，化合物（4d）和（5h）在这两种测定中表现出显著的抗氧化特性，而化合物（4e）的抗氧化特性则略低于抗坏血酸。对21种化合物针对8种微生物（阴性革兰氏菌和阳性革兰氏菌）进行了抗菌活性测试。与抗生素标准阿莫西林和庆大霉素相比，化合物（4d）和（5d）表现出显著的抗菌活性。
• Difluorocarbene-Mediated Cascade Cyclization: The Multifunctional Role of Ruppert–Prakash Reagent
  作者：Yanyao Cai、Wenjie Zhu、Shujuan Zhao、Chanjuan Dong、Zhenchuang Xu、Yanchuan Zhao

  DOI：10.1021/acs.orglett.1c00962

  日期：2021.5.7

  bipolar CF2 building block, which enables a homologation cyclization process via sequentially reacting with the phenolate and the ester group on the same substrate. The potential application of this synthetic approach is demonstrated by a late-stage modification of diethylstilbestrol. Mechanistic studies revealed the multiple crucial roles played by the Ruppert–Prakash reagent.

  用于快速访问甲二氟卡宾体介导级联环化反应偕-二氟化的3-香豆冉酮衍生物被开发。二氟卡宾用作双极CF 2构件，可通过与同一底物上的酚盐和酯基顺序反应来实现同源环化过程。己烯雌酚的后期修饰证明了这种合成方法的潜在应用。机理研究表明，Ruppert-Prakash试剂具有多种关键作用。