2-ethyl-5-(phenylmethyl)-1,3,4-oxadiazole | 754235-60-4

• 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-ethyl-5-(phenylmethyl)-1,3,4-oxadiazole
• 英文别名: 2-benzyl-5-ethyl-1,3,4-oxadiazole
• CAS: 754235-60-4
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: AQSURMIDLVBCMP-UHFFFAOYSA-N

物化性质

• 沸点：
  324.2±35.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  苯乙酸肼 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 2-ethyl-5-(phenylmethyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  DDQ促进酰肼和醛合成2,5-二取代1,3,4-恶二唑的研究

  摘要：

  据报道，通过 N-酰基腙的氧化环化，可以轻松逐步合成 2,5-二取代的 1,3,4-恶二唑。2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）可有效促进该反应，以高收率和相对较短的时间提供所需的产物。最终的 1,3,4-恶二唑衍生物也是通过单锅法直接从酰肼和醛合成的。详细讨论了所报告转化的底物范围和局限性。

  DOI：

  10.3998/ark.5550190.p009.668

文献信息

• Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
  作者：Vivek Polshettiwar、Rajender S. Varma

  DOI：10.1016/j.tetlet.2007.11.165

  日期：2008.1

  A novel one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles by condensation of acid hydrazide and triethyl orthoalkanates under microwave irradiations is reported. This green protocol was catalyzed efficiently by solid supported Nafion®NR50 and phosphorus pentasulfide in alumina (P4S10/Al2O3) with excellent yields.

  报道了在微波辐射下通过酰肼与原烷基三乙基酯的缩合反应得到的一种新颖的无锅无溶剂合成1,3,4-恶二唑和1,3,4-噻二唑的方法。此绿色协议是有效地由固体负载的Nafion催化® NR50和五硫化二磷在氧化铝（P 4小号10 /的Al 2 ö 3具有优良的产率）。
• The synthesis of bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides and other related 1,3,4-oxadiazoles from 1,1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters
  作者：Agnieszka Kudelko

  DOI：10.1016/j.tet.2011.09.018

  日期：2011.11

  1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters in the presence of catalytic amount of glacial acetic acid resulted in the formation of three heterocyclic products: the appropriate bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides, 2-benzyl-1,3,4-oxadiazoles and 2-benzoyl-1,3,4-oxadiazoles. The presence of the latter two compounds is connected with carbon–sulfur fission in the molecule

  在催化量的冰醋酸存在下，对称的1,1'-二苯基硫代二乙酸二酰肼与三乙基原酸酯的反应导致形成三种杂环产物：适当的双（1,3,4-恶二唑-2-基-苯甲基）硫化物，2-苄基-1,3,4-恶二唑和2-苯甲酰基-1,3,4-恶二唑。后两种化合物的存在与起始酰肼分子中的碳硫裂变有关。通过由苯基乙酸酰肼和2-羟甲基-1,3,4-恶二唑衍生物并行合成模型1,3,4-恶二唑，证实了未预期的裂变产物的身份。
• Nicotinamide Derivatives
  申请人：Crawforth James Michael

  公开号：US20110306597A1

  公开（公告）日：2011-12-15

  The present invention relates to compounds of the formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are defined herein, to compositions containing such compounds and to the uses of such compounds for the treatment of allergic and respiratory conditions.

  本发明涉及公式(I)的化合物及其药学上可接受的盐和溶剂，其中取代基在此定义，以及包含这种化合物的组合物，以及这种化合物用于治疗过敏和呼吸系统疾病的用途。
• Reactions of α-mercaptocarboxylic acid hydrazides with triethyl orthoesters: synthesis of 1,3,4-thiadiazin-5(6H)-ones and 1,3,4-oxadiazoles
  作者：Agnieszka Kudelko

  DOI：10.1016/j.tet.2012.02.071

  日期：2012.5

  Reactions of alpha-mercapto-beta-phenylpropionic and alpha-mercaptophenylacetic acid hydrazides with triethyl orthoesters were conducted under N-2 in glacial acetic acid and resulted in the formation of two groups of products, derivatives of 1,3,4-thiadiazin-5(6H)-ones and 2-(1-mercaptomethyl)-1,3,4-oxadiazoles. When conducting the same transformations on a-mercaptophenylacetic acid hydrazide in the presence of air, two different products from the 1,3,4-oxadiazole family, the appropriate bis(1,3,4-oxadiazol-2-ylphenylmethyl) disulfides and 2-benzy1-1,3,4-oxadiazoles, were formed with the liberation of free sulfur. The oxygenated bis(1,3,4-oxadiazol-2-yl-phenylmethyl) disulfides were reduced to the corresponding 2-(1-mercaptomethyl)-1,3,4-oxadiazoles with the use of zinc powder under mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.
• Study on DDQ-promoted synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from acid hydrazides and aldehydes
  作者：Karolina Jasiak、Agnieszka Kudelko、Wojciech Zieliński、Nikodem Kuźnik

  DOI：10.3998/ark.5550190.p009.668

  日期：——

  A facile stepwise synthesis of 2,5‐disubstituted 1,3,4‐oxadiazoles proceeding via oxidative cyclization of N‐acylhydrazones is reported. The reaction is efficiently promoted by 2,3‐dichloro‐5,6‐dicyano‐1,4‐ benzoquinone (DDQ) to afford the desired products mostly in high yields and in relatively short times. The final 1,3,4‐oxadiazole derivatives are also synthesized directly from acid hydrazides and

  据报道，通过 N-酰基腙的氧化环化，可以轻松逐步合成 2,5-二取代的 1,3,4-恶二唑。2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）可有效促进该反应，以高收率和相对较短的时间提供所需的产物。最终的 1,3,4-恶二唑衍生物也是通过单锅法直接从酰肼和醛合成的。详细讨论了所报告转化的底物范围和局限性。