ethyl 2-(2-phenoxyphenyl)acetate | 1417512-55-0

• 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: ethyl 2-(2-phenoxyphenyl)acetate
• 英文别名: (2-Phenoxy-phenyl)-acetic acid ethyl ester
• CAS: 1417512-55-0
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: QYKUDVPDWPLJIF-UHFFFAOYSA-N

物化性质

• 沸点：
  344.1±25.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-phenoxyphenyl)acetate 在 碳酸氢钠 、 一水合肼 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 30.58h， 生成 5-ethoxy-3-(2-phenoxybenzyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles

  摘要：

  The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4-oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed similar to superior binding affinity to the GABA(A)/benzodiazepine receptor complex, relative to diazepam as the reference drug. Among them, 5-(4-chloro-2-(2-fluorophenoxy) benzyl)-3-benzylthio-4H-1,2,4-triazole (8l) showed the highest affinity (IC50 = 0.892 nM) relative to diazepam (IC50 = 2.857 nM) and also showed the most increase in pentylen-etetrazole-induced seizure threshold relative to diazepam as the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.041
• 作为产物：
  描述：

  邻苯氧基苯甲醇 在 吡啶 、 氯化亚砜 、 potassium hydroxide 作用下， 以 二甲基亚砜 、 正丁醇 、 苯 为溶剂， 反应 34.0h， 生成 ethyl 2-(2-phenoxyphenyl)acetate
  参考文献：
  名称：

  Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles

  摘要：

  The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4-oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed similar to superior binding affinity to the GABA(A)/benzodiazepine receptor complex, relative to diazepam as the reference drug. Among them, 5-(4-chloro-2-(2-fluorophenoxy) benzyl)-3-benzylthio-4H-1,2,4-triazole (8l) showed the highest affinity (IC50 = 0.892 nM) relative to diazepam (IC50 = 2.857 nM) and also showed the most increase in pentylen-etetrazole-induced seizure threshold relative to diazepam as the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.041

文献信息

• Regioselective Arene C−H Alkylation Enabled by Organic Photoredox Catalysis
  作者：Natalie Holmberg‐Douglas、Nicholas P. R. Onuska、David A. Nicewicz

  DOI：10.1002/anie.202000684

  日期：2020.5.4

  metallocarbene species, which is capable of direct insertion into an aromatic C-H bond. However, these high-energy intermediates can often require directing groups or a large excess of substrate to achieve efficient and selective reactivity. Herein, we report that arene cation radicals generated by organic photoredox catalysis engage in formal C-H functionalization reactions with diazoacetate derivatives, furnishing

  扩展适用于复杂分子后期修饰的 CH 官能化反应工具箱是药物化学领域的热点，其中已知药效团的结构变体的制备是药物开发的关键策略。芳香族分子功能化的一种方式是利用重氮化合物和过渡金属催化剂来生成金属卡宾物质，该物质能够直接插入芳香族CH键中。然而，这些高能中间体通常需要导向基团或大量过量的底物才能实现高效和选择性的反应。在此，我们报道有机光氧化还原催化产生的芳烃阳离子自由基与重氮乙酸衍生物进行正式的CH官能化反应，提供具有中等到良好区域选择性的sp2-sp3偶联产物。与之前使用金属卡宾中间体的方法相比，这种转化不通过卡宾中间体进行，也不需要过渡金属催化剂的存在。
• Selective synthesis of arylacetic acid esters from ethyl acetoacetate and aryl halides in the presence of copper(II) on 4Å molecular sieves
  作者：Dávid Zsolczai、János Németh、Zoltán Hell

  DOI：10.1016/j.tetlet.2015.09.136

  日期：2015.11

  A heterogeneous catalyst, copper(II) on 4 Å molecular sieves has successfully been used in the arylation of ethyl acetoacetate, selectively forming arylacetic esters in high yields. The air stable and easily handled catalyst can be simply filtered off during purification thus avoiding significant metal contamination of the product.

  一种多相催化剂，在4Å分子筛上的铜（II）已成功用于乙酰乙酸乙酯的芳基化，可高产率选择性地形成芳基酸酯。空气稳定且易于处理的催化剂可以在纯化过程中简单地滤出，从而避免了产品的重大金属污染。
• A Cu-Catalysed Radical Cross-Dehydrogenative Coupling Approach to Acridanes and Related Heterocycles
  作者：Timothy E. Hurst、Richard J. K. Taylor

  DOI：10.1002/ejoc.201601336

  日期：2017.1.3

  The synthesis of acridanes and related compounds through a Cu‐catalysed radical cross‐dehydrogenative coupling of simple 2‐[2‐(arylamino)aryl]malonates is reported. This method can be further streamlined to a one‐pot protocol involving the in situ fomation of the 2‐[2‐(arylamino)aryl]malonate by α‐arylation of diethyl malonate with 2‐bromodiarylamines under Pd catalysis, followed by Cu‐catalysed cyclisation

  据报道，通过简单的 2-[2-(芳基氨基)芳基]丙二酸酯的铜催化自由基交叉脱氢偶联合成吖啶类和相关化合物。该方法可以进一步简化为一锅法，涉及通过丙二酸二乙酯与 2-溴二芳基胺在 Pd 催化下进行 α-芳基化，然后在 Cu 催化下原位形成 2-[2-(芳基氨基)芳基]丙二酸酯环化。