2-羟基-6-甲基苯甲酸甲酯 | 33528-09-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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-6-甲基苯甲酸甲酯
• 英文名称: methyl 6-methylsalicylate
• 英文别名: methyl 2-hydroxy-6-methylbenzoate
• CAS: 33528-09-5
• 化学式: C₉H₁₀O₃
• mdl: MFCD06797968
• 分子量: 166.177
• InChiKey: GPNCYIZKJTXKRO-UHFFFAOYSA-N

物化性质

• 熔点：
  31-32 °C
• 沸点：
  230.2±20.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)
• 保留指数：
  1970

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 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
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-羟基-6-甲基苯甲酸甲酯 在 sodium hydroxide 作用下， 生成 2-羟基-6-甲基苯甲酸
  参考文献：
  名称：

  Aghoramurthy et al., Chemistry and industry, 1954, p. 1327

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,5-trimethyl-4H-benzo[d][1,3]dioxin-4-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以72%的产率得到2-羟基-6-甲基苯甲酸甲酯
  参考文献：
  名称：

  The Scent of Bacteria: Headspace Analysis for the Discovery of Natural Products

  摘要：

  Volatile compounds released by 50 bacterial strains, 45 of them actinobacteria in addition to three chloroflexi and two myxobacteria, have been collected by use of a closed-loop stripping apparatus, and the obtained headspace extracts have been analyzed by GC-MS. Excluding terpenes that have recently been published elsewhere, 254 compounds from all kinds of compound classes have been identified. For unambiguous compound identification several reference compounds have been synthesized. Among the detected volatiles 12 new natural products have been found, in addition to mellein, which was released by Saccharopolyspora erythraea. The iterative PKS for this compound has recently been identified by in vitro experiments, but mellein production in S. erythraea has never been reported before. These examples demonstrate that headspace analysis is an important tool for the discovery of natural products that may be overlooked using conventional techniques. The method is alos useful for feeding experiments with isotopically labeled precursors and was applied to investigate the biosynthesis of the unusual nitrogen compound 1-nitro-2-methylpropane, which arises from valine. Furthermore, several streptomycetes emitted compounds that were previously recognized as insect pheromones, thus questioning if bacterial symbionts are involved in insect communication.

  DOI：

  10.1021/np300468h

文献信息

• Vitamin Catalysis: Direct, Photocatalytic Synthesis of Benzocoumarins via (−)-Riboflavin-Mediated Electron Transfer
  作者：Tobias Morack、Jan B. Metternich、Ryan Gilmour

  DOI：10.1021/acs.orglett.8b00052

  日期：2018.3.2

  photoactivated (−)-riboflavin (vitamin B2) to generate the heterocyclic core via photoinduced single electron transfer. Collectively, the inexpensive nature of the catalyst, ease of execution, and absence of external metal additives are a convincing endorsement for the incorporation of simple vitamins in contemporary catalysis.

  公开了一种操作简单的方案，以促进直接从联芳基羧酸进入苯并-3,4-香豆素，而无需底物预官能化。作为经典内酯化策略的补充，这种分离依赖于光活化的（-）-核黄素（维生素B 2）的氧化能力，可通过光诱导的单电子转移生成杂环核。总的来说，催化剂的廉价性质，易于实施以及不存在外部金属添加剂，都令人信服地赞同将简单的维生素掺入现代催化剂中。
• 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。
• 一种制备多取代占吨酮类衍生物的方法
  申请人：清华大学

  公开号：CN106977489B

  公开（公告）日：2019-05-31

  本发明公开了一种制备多取代占吨酮类衍生物的方法。所述方法为，向反应器中将二芳基碘化合物，抽换氮气完毕后，在氮气保护下加入水杨酸酯类衍生物化合物与溶剂，加热反应，反应完毕后分离提纯得到多取代占吨酮类衍生物，反应温度为：40‑150℃；反应时间为：1‑24h；本发明所提供的多取代占吨酮衍生物的制备方法科学合理，合成方法具有简单、产率高、产品易于纯化等特点。
• Concise synthesis of xanthones by the tandem etherification—Acylation of diaryliodonium salts with salicylates
  作者：Gaoxiaozheng Liu、Chao Wu、Bifeng Chen、Ru He、Chao Chen

  DOI：10.1016/j.cclet.2017.11.046

  日期：2018.6

  Abstract An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation to give target heterocycles in good yields (up to 91%). Multi-substituted xanthones were gained by shifting the substituent of salicylates or

  摘要建立了一种高效的多取代氧杂蒽合成方法。将二芳基碘鎓盐和水杨酸酯的反应用于制备氧杂蒽。此方法通过分子间醚化酰化进行，以高收率（最高91％）得到目标杂环。通过取代水杨酸盐或二芳基碘鎓盐的取代基获得多取代的氧杂蒽
• New Antianginal Nitro Esters with Reduced Hypotensive Activity. Synthesis and Pharmacological Evaluation of 3-[(Nitrooxy)alkyl]-2H-1,3-benzoxazin-4(3H)-ones
  作者：Francesca Benedini、Giorgio Bertolini、Roberta Cereda、Giancarlo Dona、Gianni Gromo、Silvio Levi、Jacques Mizrahi、Alberto Sala

  DOI：10.1021/jm00001a018

  日期：1995.1

  anti-ischemic and hemodynamic profile after oral (po) administration. These new nitro ester derivatives, endowed with a marked antianginal activity, which is not associated with concurrent and pronounced falls in systemic blood pressure, represent the leads of a new class of selective nitrovasodilators having a preferential action on large coronary vessels, which could be clinically relevant in the treatment

  新的硝基酯3-[（（硝基氧基）烷基] -2H-1,3-苯并恶嗪-4（3H）-酮显示出对局部缺血引起的心电图变化的显着抑制活性，仅具有有限的全身血流动力学作用，目前已有报道研究。这些新的硝基血管舒张剂是在麻醉的大鼠中通过静脉或冠状动脉内注射Arg血管加压素或乙酰甲胆碱诱导的心电图T波和ST段抬高的有效抑制剂。活性最高的化合物的效力分别比三硝酸甘油酯或尼古拉地尔高300到600倍。这些硝酸酯以浓度依赖性的方式使分离出的兔主动脉松弛，其浓度比三硝酸甘油酯高（2-40倍），并以比三硝酸甘油酯发挥类似降压作用所需的剂量高7-300倍的剂量降低平均动脉血压。值得注意的是，这些化合物在口服（po）给药后仍保持其抗缺血和血流动力学特征。这些新的硝基酯衍生物具有显着的抗心绞痛活性，与全身性血压的同时并发明显下降无关，它们代表了对大冠状血管具有优先作用的新型选择性硝化血管舒张剂的产生。与冠状动脉疾病的治疗有关。