butyl 2-(4-methoxyphenyl)acetate | 104548-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: butyl 2-(4-methoxyphenyl)acetate
• CAS: 104548-38-1
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: DACRGZJKNATRGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  正溴丁烷 、 对甲氧基苯乙酸 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 水 、 氯苯 为溶剂， 反应 5.0h， 生成 butyl 2-(4-methoxyphenyl)acetate
  参考文献：
  名称：

  Phase-Transfer-Catalyzed Synthesis of Butyl 4-Methoxyphenylacetate and Its Simultaneous Hydrolysis by Potassium Hydroxide in Oil–Water Biphasic System

  摘要：

  在此，我们首次报告在二相介质中使用氢氧化钾进行丁基4-甲氧基苯乙酸酯的相转移催化合成过程中同时发生水解的情况。本文介绍了操作参数对反应的影响。酯的产率随着搅拌速度的增加而提高，直至500 rpm，超过此速度后，转化率不再受搅拌速度的影响。在较高浓度的碱下，水解产物更为有利。较低的温度和较大的水体积有利于酯化。在催化剂浓度较高时，酯的产率显著下降。在存在高度极性溶剂的情况下，酯的转化率最初增加，随后又出现急剧下降。针对这一现象，基于结果给出了合理的解释。

  DOI：

  10.1246/bcsj.20120055

文献信息

• Rhodium(I) catalyzed carbonylation reactions of halides and ethers
  作者：Caroline Buchan、Nathalie Hamel、James B. Woell、Howard Alper

  DOI：10.1016/s0040-4039(00)98913-5

  日期：——
• 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.
• Phase-Transfer-Catalyzed Synthesis of Butyl 4-Methoxyphenylacetate and Its Simultaneous Hydrolysis by Potassium Hydroxide in Oil–Water Biphasic System
  作者：Maw-Ling Wang、Perumberkandigai Adikesavan Vivekanand、Ming-Chan Yu

  DOI：10.1246/bcsj.20120055

  日期：2012.9.15

  Herein, we report for the first time simultaneous hydrolysis during the phase-transfer-catalyzed synthesis of butyl 4-methoxyphenylacetate using potassium hydroxide in biphasic medium. Effect of operating parameters on the reaction is presented. The yield of ester increases with the increase in the agitation speed up to 500 rpm and above that the conversion is not influenced by the agitation speed. At higher concentration of base, the hydrolysis product is more favored. Lower temperature and larger volume of water favors the esterfication. At high concentration of catalyst, sharp decrease in the yield of the ester is noticed. In the presence of highly polar solvents, the conversion of ester increases initially and then there was a sharp decrease. Rational explanations to account for the phenomena based on the results are made.

  在此，我们首次报告在二相介质中使用氢氧化钾进行丁基4-甲氧基苯乙酸酯的相转移催化合成过程中同时发生水解的情况。本文介绍了操作参数对反应的影响。酯的产率随着搅拌速度的增加而提高，直至500 rpm，超过此速度后，转化率不再受搅拌速度的影响。在较高浓度的碱下，水解产物更为有利。较低的温度和较大的水体积有利于酯化。在催化剂浓度较高时，酯的产率显著下降。在存在高度极性溶剂的情况下，酯的转化率最初增加，随后又出现急剧下降。针对这一现象，基于结果给出了合理的解释。