3-甲氧基水杨酸乙酯 | 35030-98-9

• 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: 3-甲氧基水杨酸乙酯
• 英文名称: ethyl 2-hydroxy-3-methoxybenzoate
• CAS: 35030-98-9
• 化学式: C₁₀H₁₂O₄
• mdl: MFCD05663711
• 分子量: 196.203
• InChiKey: LTNLJNRZBZABNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  119-122 °C(Press: 1 Torr)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  3-甲氧基水杨酸乙酯 在 sodium methylate 、 potassium carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 14.0h， 生成 (羟基-3-甲氧基-7-苯并呋喃基-2)-羧酸甲酯
  参考文献：
  名称：

  Lamotte; Demerseman; Royer, European Journal of Medicinal Chemistry, 1986, vol. 21, # 5, p. 379 - 383

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2,3-dimethoxybenzoate 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到3-甲氧基水杨酸乙酯
  参考文献：
  名称：

  AlCl 3促进邻位取代芳基甲基醚的轻松去甲基化

  摘要：

  已经开发出使用 AlCl3 对邻位取代的芳基甲基醚进行有效和实用的去甲基化。该方法转化率高，操作简单，成本低廉。提出了一种涉及 AlCl3 与 OMe 和相邻吸电子基团络合的机制。去甲基化过程中可以容忍许多官能团，29个例子以90-98％的产率得到了去甲基化产物。

  DOI：

  10.3184/030823410x12708998015900

文献信息

• Pd-Catalyzed CH Oxygenation with TFA/TFAA: Expedient Access to Oxygen-Containing Heterocycles and Late-Stage Drug Modification
  作者：Gang Shan、Xinglin Yang、Linlin Ma、Yu Rao

  DOI：10.1002/anie.201207458

  日期：2012.12.21

  Acid brings the oxygen: A general method for palladium‐catalyzed CH oxygenation has been developed for the facile synthesis of a wide range of functionalized phenols with readily available aryl ketones, benzoates, benzamides, acetanilides, and sulfonamides. A trifluoroacetic acid/trifluoroacetic acid anhydride solvent system serves as the oxygen source and is the critical factor for CH activation

  酸带来氧气：已开发出一种通用的钯催化CH氧化方法，可轻松合成各种功能化的酚，并带有易得的芳基酮，苯甲酸酯，苯甲酰胺，对乙酰苯胺和磺酰胺。三氟乙酸/三氟乙酸酐溶剂体系用作氧气源，是CH活化的关键因素。
• 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。
• Synthesis, antibacterial activity, and quantitative structure–activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3()-benzofuranone derivatives
  作者：Narges Hadj-esfandiari、Latifeh Navidpour、Hooman Shadnia、Mohsen Amini、Nasrin Samadi、Mohammad Ali Faramarzi、Abbas Shafiee

  DOI：10.1016/j.bmcl.2007.09.062

  日期：2007.11

  A new series of (Z)-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2H)-benzofuranones (11a-p) and (Z)-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2H)-benzofuranones (12a-m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a-p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a-m) were not effective against selected bacteria. The quantitative structure-activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities. (C) 2007 Elsevier Ltd. All rights reserved.
• Freedman, Jules; Stewart, Kenneth T., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1547 - 1554
  作者：Freedman, Jules、Stewart, Kenneth T.

  DOI：——

  日期：——
• Ruthenium(II)-Catalyzed Synthesis of Hydroxylated Arenes with Ester as an Effective Directing Group
  作者：Yiqing Yang、Yun Lin、Yu Rao

  DOI：10.1021/ol301104n

  日期：2012.6.1

  An unprecedented Ru(II) catalyzed ortho-hydroxylation has been developed for the facile synthesis of a variety of multifunctionalized arenes from easily accessible ethyl benzoates with ester as an efficient directing group. Both the TFA/TFAA cosolvent system and oxidants serve as the critical success factors in this transformation. The reaction demonstrates excellent reactivity, good functional group tolerance, and high yields.