propyl 2-(4-methoxyphenyl)acetate | 500284-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: propyl 2-(4-methoxyphenyl)acetate
• CAS: 500284-52-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: RIEKNUTZBRBQRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酸 、 溴丙烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 以82%的产率得到propyl 2-(4-methoxyphenyl)acetate
  参考文献：
  名称：

  Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them

  摘要：

  A group of 4-methoxyphenylacetic acid esters were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compounds 7d-e showed the best IC50 in SLO inhibition (IC50 = 3.8 and 1.9 mu M, respectively). All compounds were docked in SLO active site and showed that carbonyl group of compounds is oriented toward the Fe-III-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of the synthetic esters in inhibiting of 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.009

文献信息

• Titanium Tetrachloride-Assisted Direct Esterification of Carboxylic Acids
  作者：Palmira Alessia Cavallaro、Marzia De Santo、Marianna Greco、Rocco Marinaro、Emilia Lucia Belsito、Angelo Liguori、Antonella Leggio

  DOI：10.3390/molecules29040777

  日期：——

  carboxylic acids and alcohols, using the Lewis acid titanium tetrachloride. Titanium tetrachloride has proven highly effective as a coupling reagent for the one-pot formation of esters from carboxylic acids and alcohols operating under mild and neutral conditions. Notably, the reaction eliminates the need for bases, yielding carboxylic esters in high purity and yields. The method is efficient, even with

  酯类化合物广泛存在于药物和天然产物中，在有机合成中发挥着至关重要的作用，促进了多种合成方法的发展。从羧酸合成酯的重要化学方法涉及羧基官能团的活化，需要将羟基转化为合适的离去基团。本文介绍了我们对使用路易斯酸四氯化钛从羧酸和醇生产酯的有效方法的研究结果。事实证明，四氯化钛作为一种偶联剂非常有效，可在温和和中性条件下由羧酸和醇一锅形成酯。值得注意的是，该反应不需要碱，从而产生高纯度和高产率的羧酸酯。该方法即使对于长链羧酸也是有效的，并且对于二氯甲烷中的伯醇也运行良好。羧酸中可能存在的空间位阻对反应具有中等影响。相反，容易形成稳定碳阳离子的醇底物需要使用非极性溶剂（例如己烷）进行反应。
• 10.1039/d4gc02052a
  作者：Liu, Yu、Xie, Shentong、Yin, Yuqing、Lu, Ming、Wang, Pengcheng、Shi, Renyi

  DOI：10.1039/d4gc02052a

  日期：——

  electrons from the cathode to organic halides, making it unsuitable for sensitive organic halides such as chloroformates. As a result, the electroreductive XEC of readily accessible chloroformates with alkyl halides for ester synthesis remains a largely unmet challenge. In this work, catalyst-free electrochemically driven cross-electrophile esterification of alkyl halides has been developed. A wide range

  电还原交叉亲电子偶联已成为构建具有挑战性的 C-C 或 C-X 键的强大而有效的方法，具有多种优势，包括高效电子转移、可调还原电位、底物直接电激活和良好的可扩展性。在电还原交叉亲电子偶联中，需要高负载量的过渡金属催化剂来促进电子从阴极转移到有机卤化物，这使得它不适合敏感的有机卤化物，例如氯甲酸酯。因此，使用易于获得的氯甲酸酯与卤代烷进行电还原 XEC 来合成酯仍然是一个尚未解决的挑战。在这项工作中，开发了无催化剂电化学驱动的烷基卤化物的交叉亲电子酯化反应。代表合成和药物化学中一类重要分子的各种 2-苯乙酸酯是在温和的反应条件下从简单且廉价的烷基卤化物和氯甲酸烷基酯获得的。各种官能团均具有良好的耐受性，产率高达 98%。该协议将为电化学驱动的交叉亲电子偶联的进一步发展做出很大贡献。
• Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them
  作者：Hamid Sadeghian、Neda Attaran、Zeinab Jafari、Mohammad Reza Saberi、Mehdi Pordel、Mohammad Mahdi Riazi

  DOI：10.1016/j.bmc.2009.02.009

  日期：2009.3

  A group of 4-methoxyphenylacetic acid esters were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compounds 7d-e showed the best IC50 in SLO inhibition (IC50 = 3.8 and 1.9 mu M, respectively). All compounds were docked in SLO active site and showed that carbonyl group of compounds is oriented toward the Fe-III-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of the synthetic esters in inhibiting of 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques. (C) 2009 Elsevier Ltd. All rights reserved.