Methyl 2-<(4-Methoxyphenyl)methoxy>benzoate | 131137-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2-<(4-Methoxyphenyl)methoxy>benzoate
• 英文别名: methyl 2-((4-methoxybenzyl)oxy)benzoate；Methyl 2-[(4-methoxyphenyl)methoxy]benzoate
• CAS: 131137-80-9
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: HTBBLVCNYVNGCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2-<(4-Methoxyphenyl)methoxy>benzoate 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以94%的产率得到水杨酸甲酯
  参考文献：
  名称：

  使用POCl 3 †进行PMB基团脱保护和清除的简便方法

  摘要：

  以POCl 3为试剂，开发了一种方便，高产的PMB醚和PMB酯中对甲氧基苄基（PMB）脱保护和清除的方法。在去保护步骤中再生了4-甲氧基苄基氯，其是用于制备PMB醚和酯的原料。这种温和而选择性的程序可以耐受几个酸敏感的官能团。

  DOI：

  10.1039/c3ra42113a
• 作为产物：
  描述：

  4-甲氧基氯苄 、 水杨酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以74%的产率得到Methyl 2-<(4-Methoxyphenyl)methoxy>benzoate
  参考文献：
  名称：

  共轭添加到3-（对甲苯磺酰基）色酮：通往2-取代的色酮和手性取代的苯并吡喃-4-酮的途径

  摘要：

  3-（对甲苯磺酰基）苯并二氢吡喃酮3a经历非对映选择性共轭加成的二甲基二甲基碳酸锂，产生2-甲基-3-（对甲苯磺酰基）苯并二氢吡喃-4-酮的混合物。将混合物加热至140℃，以定量产率得到2-甲基色酮。来自（S）-3a的混合产物脱硫得到具有90％ee的（S）-2-甲基苯并-4-酮。在甲基添加过程中，羰基和亚砜氧的螯合导致了非对映异构。

  DOI：

  10.1016/s0040-4020(01)96020-x

文献信息

• Synthesis of Unsymmetrical Benzil Licoagrodione
  作者：Rattana Worayuthakarn、Sasiwadee Boonya-udtayan、Eakarat Arom-oon、Poonsakdi Ploypradith、Somsak Ruchirawat、Nopporn Thasana

  DOI：10.1021/jo8013353

  日期：2008.9.19

  A synthesis of unsymmetrical 1,2-diarylethane-1,2-dione is reported involving the intramolecular cyclization of anionic benzylic ester of the aryl benzyl ether followed by oxidation employing dioxirane. With the use of microwave irradiation, licoagrodione was prepared from Claisen rearrangement of the corresponding allyl phenyl ether 1,2-diketone readily available from the Lindlar's reduction of the

  据报道，不对称的1,2-二芳基乙烷-1，2-二酮的合成涉及芳基苄基醚的阴离子苄基酯的分子内环化，然后使用二环氧乙烷进行氧化。使用微波辐射，由对应的烯丙基苯基醚1，2-二酮的克莱森重排制备了甘草二酮，其可容易地从相应的炔烃衍生物的Lindlar's还原中获得。随后除去保护基，然后得到所需的产物。
• Design, synthesis and molecular docking of salicylic acid derivatives containing metronidazole as a new class of antimicrobial agents
  作者：Zhi-Hua Guo、Yong Yin、Cong Wang、Peng-Fei Wang、Xing-Tao Zhang、Zhong-Chang Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2015.07.075

  日期：2015.9

  A series of novel salicylic acid derivatives containing metronidazole as Staphylococcus aureus Tyrosyl-tRNA synthetase (TyrRS) inhibitors have been synthesized and evaluated their biology activities as potential antibacterial agents. Among these compounds, compound 5r exhibited the most potent antibacterial activity against Gram-positive (S. aureus ATCC 6538 and Bacillus subtilis ATCC 6633) and Gram-negative (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525) with MICs of 0.39-1.57 mu g/mL and showed the most potent S. aureus Tyrosyl-tRNA synthetase inhibitory with 2.3 mu M. Docking simulation was performed to insert compound 5r into the crystal structure of S. aureus Tyrosyl-tRNA synthetase active site to determine the probable binding model. These results suggested that compound 5r may be a promising antibacterial agent. (c) 2015 Elsevier Ltd. All rights reserved.
• Cleavage or Acetyl-de-alkylation of 4-Methoxybenzyl (MPM) Ethers Using Acetic Acid
  作者：Kevin J. Hodgetts、Timothy W. Wallace

  DOI：10.1080/00397919408011711

  日期：1994.4

  Aryl (4-methoxyphenyl)methyl (MPM) ethers are cleaved by heating with acetic acid for a few hours at 90-degrees-C, producing the corresponding phenols and (4-methoxyphenyl)methyl acetate. Under the same conditions alkyl MPM ethers are transformed directly into the corresponding alkyl acetates.
• A convenient approach for the deprotection and scavenging of the PMB group using POCl3
  作者：Andivelu Ilangovan、Shanmugasundar Saravanakumar、Subramani Malayappasamy、Govindaswamy Manickam

  DOI：10.1039/c3ra42113a

  日期：——

  convenient and high yielding approach for the deprotection and scavenging of the p-methoxybenzyl (PMB) group in PMB ethers and PMB esters was developed using POCl3 as the reagent. 4-Methoxybenzyl chloride, a starting material used for the preparation of PMB ethers and esters was regenerated in the deprotection step. This mild and selective procedure tolerates several acid sensitive functional groups.

  以POCl 3为试剂，开发了一种方便，高产的PMB醚和PMB酯中对甲氧基苄基（PMB）脱保护和清除的方法。在去保护步骤中再生了4-甲氧基苄基氯，其是用于制备PMB醚和酯的原料。这种温和而选择性的程序可以耐受几个酸敏感的官能团。
• Conjugate addition to 3-(ptolylsulphinyl)chromone: a route to 2-substituted chromones and chiral substituted chroman-4-ones
  作者：Suthiweth T. Saengchantara、Timothy W. Wallace

  DOI：10.1016/s0040-4020(01)96020-x

  日期：1990.1

  3-(p-Tolylsulphinyl)chromone 3a undergoes diastereoselective conjugate addition of lithium dimethylcuprate, producing a mixture of 2-methyl-3-(p-tolylsulphinyl)chroman-4-ones. Heating the mixture to 140°C gives 2-methylchromone in quantitative yield. Desulphurisation of the mixed products from (S)-3a gives (S)-2-methylchroman-4-one with 90% e.e. Chelation of the carbonyl and sulphoxide oxygens during

  3-（对甲苯磺酰基）苯并二氢吡喃酮3a经历非对映选择性共轭加成的二甲基二甲基碳酸锂，产生2-甲基-3-（对甲苯磺酰基）苯并二氢吡喃-4-酮的混合物。将混合物加热至140℃，以定量产率得到2-甲基色酮。来自（S）-3a的混合产物脱硫得到具有90％ee的（S）-2-甲基苯并-4-酮。在甲基添加过程中，羰基和亚砜氧的螯合导致了非对映异构。