2-(4-chlorobenzyl)-5-phenyl-1,3,4-oxadiazole | 950272-35-2

• 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: 2-(4-chlorobenzyl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-[(4-Chlorophenyl)methyl]-5-phenyl-1,3,4-oxadiazole
• CAS: 950272-35-2
• 化学式: C₁₅H₁₁ClN₂O
• mdl: MFCD13969240
• 分子量: 270.718
• InChiKey: KCHVVRPBZRNMAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 5-(4-氯苄基)-2H-四唑 在 吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 200.0 ℃ 、1.0 MPa 条件下， 反应 0.13h， 以88%的产率得到2-(4-chlorobenzyl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  High-temperature continuous flow synthesis of 1,3,4-oxadiazoles via N-acylation of 5-substituted tetrazoles

  摘要：

  Applying continuous flow processing in a high-temperature/high-pressure regime (200-220 degrees C, 11-14 bar) 2,5-disubstituted-1,3,4-oxadiazoles are prepared in high yields within 5-10 min residence time by treatment of 5-substituted-1H-tetrazoles with anhydrides or acid chlorides as electrophiles (Huisgen reaction). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.043

文献信息

• Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles
  作者：Alexander V. Aksenov、Vladislav Khamraev、Nicolai A. Aksenov、Nikita K. Kirilov、Dmitriy A. Domenyuk、Vladimir A. Zelensky、Michael Rubin

  DOI：10.1039/c9ra00976k

  日期：——

  A novel methodology for general and chemoselective preparation of non-symmetric 1,3,4-oxadiazoles is developed. This unusual reaction proceeds via polyphosphoric acid-assisted activation of nitroalkanes towards nucleophilic attack with acylhydrazides.

  开发了一种用于非对称 1,3,4-恶二唑的通用和化学选择性制备的新方法。这种不寻常的反应是通过多磷酸辅助的硝基烷烃活化向酰基肼的亲核攻击而进行的。
• A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions
  作者：Kazuyuki Tokumaru、Jeffrey N. Johnston

  DOI：10.1039/c7sc00195a

  日期：——

  aromatic heterocycle valued for its low-lipophilicity in drug development. Substituents at the 2- and/or 5-positions can modulate the heterocycle's electronic and hydrogen bond-accepting capability, while exploiting its use as a carbonyl bioisostere. A new approach to 1,3,4-oxadiazoles is described wherein α-bromo nitroalkanes are coupled to acyl hydrazides to deliver the 2,5-disubstituted oxadiazole directly

  1,3,4-恶二唑是一种芳香杂环，因其低亲脂性而在药物开发中具有重要价值。2-和/或5-位的取代基可以调节杂环的电子和氢键接受能力，同时利用其作为羰基生物等排体的用途。描述了一种制备 1,3,4-恶二唑的新方法，其中 α-溴硝基烷烃与酰肼偶联以直接提供 2,5-二取代恶二唑，避免了 1,2-二酰肼中间体。通过利用手性 α-溴硝基烷或氨基酸酰肼底物，可以改善恶二唑取代仲胺新结构单元的获得。与依赖高亲氧性试剂来实现不对称 1,2-二酰肼环化的替代方案相比，恶二唑合成的非脱水条件尤其值得注意。通过标准水洗直接去除副产物，打破了温和的条件。
• High-temperature continuous flow synthesis of 1,3,4-oxadiazoles via N-acylation of 5-substituted tetrazoles
  作者：Benedikt Reichart、C. Oliver Kappe

  DOI：10.1016/j.tetlet.2011.12.043

  日期：2012.2

  Applying continuous flow processing in a high-temperature/high-pressure regime (200-220 degrees C, 11-14 bar) 2,5-disubstituted-1,3,4-oxadiazoles are prepared in high yields within 5-10 min residence time by treatment of 5-substituted-1H-tetrazoles with anhydrides or acid chlorides as electrophiles (Huisgen reaction). (C) 2011 Elsevier Ltd. All rights reserved.