3-cyclohexyl-5-phenyl-1,2,4-oxadiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-cyclohexyl-5-phenyl-1,2,4-oxadiazole
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: BOMTUBVUSUAXBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  环己甲腈 在 aluminum oxide 、 氟化铵 、 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.05h， 生成 3-cyclohexyl-5-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  氧化铝负载的氟化铵在无溶剂条件下合成1,2,4-恶二唑的新方法

  摘要：

  发现氧化铝负载的氟化铵是在无溶剂条件下使用微波辐射合成酰胺肟的1,2,4-恶二唑的有效试剂。该方法是一种从pot胺肟和酰氯合成1,2,4-恶二唑衍生物的一锅法，简便，快速，高产。在没有氟化铵的氧化铝存在下，mid胺肟与酰氯的反应仅得到相应的O-酰氨基肟为主要产物。

  DOI：

  10.1002/jhet.5570420434

文献信息

• Copper-Catalyzed Direct Synthesis of 1,2,4-Oxadiazoles from Amides and Organic Nitriles by Oxidative N-O Bond Formation
  作者：Malleswara Rao Kuram、Woo Gyum Kim、Kyungjae Myung、Sung You Hong

  DOI：10.1002/ejoc.201501502

  日期：2016.1

  Cu-catalyzed one-step method for the synthesis of 1,2,4-oxadiazoles from stable, less toxic, and readily available amides and organic nitriles by a rare oxidative N–O bond formation using O2 as sole oxidant. This method has a broad substrate scope and a good tolerance for diverse functional groups. Moreover, the synthetic utility of this method is highlighted by the synthesis of biologically active 3,5-disubstituted

  在此，我们报告了第一个 Cu 催化一步法，通过使用 O2 作为唯一的稀有氧化 N-O 键，从稳定、毒性较低且易于获得的酰胺和有机腈合成 1,2,4-恶二唑。氧化剂。该方法具有广泛的底物范围和对不同官能团的良好耐受性。此外，该方法的合成效用通过具有生物活性的 3,5-二取代衍生物的合成而突出。
• Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones
  作者：Feng-Lian Zhang、Yi-Feng Wang、Shunsuke Chiba

  DOI：10.1039/c3ob41393d

  日期：——

  Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60 °C under an O2 atmosphere via benzylic C–H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs2CO3 in DMSO at 100 °C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.

  通过在60°C下，在O2气氛中使用K3PO4作为催化剂，将N-苄基脒肟在DMF中加热，实现了1,2,4-噁二唑的简洁合成，这一过程涉及苄基C-H氧合作用。另一方面，在100°C下，使用Cs2CO3作为催化剂，在DMSO中对N-苄基脒脟进行需氧处理，可能导致骨架氧化重排，主要产物为喹唑啉酮。这种正交的产品选择性可以通过反应温度、溶剂和无机碱的选择来实现。
• Magnesia-supported hydroxylamine hydrochloride in the presence of sodium carbonate as an efficient reagent for the synthesis of 1,2,4-oxadiazoles from nitriles
  作者：Babak Kaboudin、Fariba Saadati

  DOI：10.1016/j.tetlet.2007.02.105

  日期：2007.4

  An efficient one-pot method has been developed for the synthesis of 1,2,4-oxadiazoles through a one-pot reaction of nitriles with hydroxylamine hydrochloride in the presence of magnesia-supported sodium carbonate followed by reaction with acyl halides under solvent-free conditions using microwave irradiation. This method is easy, rapid and good yielding.

  已开发出一种有效的一锅法，该方法通过在氧化镁负载的碳酸钠存在下，腈与盐酸羟胺一锅反应，然后在无溶剂下与酰卤反应，来合成1,2,4-恶二唑使用微波照射的条件。该方法简便，快速且产率高。
• Manganese oxide nanoparticles supported on graphene oxide as an efficient nanocatalyst for the synthesis of 1,2,4‐oxadiazoles from aldehydes
  作者：Fariba Saadati、Babak Kaboudin、Rana Hasanloei、Zeinab Namazifar、Xavier Marset、Gabriela Guillena

  DOI：10.1002/aoc.5838

  日期：2020.10

  The easy synthesis of graphene oxide (GO)‐supported manganese dioxide (MnO2) nanoparticles as a stable heterogeneous nanocatalyst (MnO2@GO) is described. This catalyst was investigated in the synthesis of 1,2,4‐oxadiazoles from amidoximes and aldehydes via a cyclization and oxidation process. The nanocomposite was prepared and characterized using various techniques. The catalytic application of the

  描述了易于合成的氧化石墨烯（GO）负载的二氧化锰（MnO 2）纳米颗粒，作为稳定的多相纳米催化剂（MnO 2 @GO）。在通过环化和氧化过程从a胺肟和醛合成1,2,4-恶二唑中对这种催化剂进行了研究。使用各种技术制备并表征了纳米复合材料。在多种醛与脂族和芳族a肟的反应中检查了纳米复合材料的催化应用。稳定而坚固的催化剂被循环使用了七次，而催化活性没有明显降低。
• Organic reactions in water: an efficient method for the synthesis of 1,2,4-oxadiazoles in water
  作者：Babak Kaboudin、Leila Malekzadeh

  DOI：10.1016/j.tetlet.2011.09.081

  日期：2011.11

  A simple and efficient process has been developed for the synthesis of 1,2,4-oxadiazoles in good yields through the reaction of amidoximes with anhydrides under catalyst-free conditions in water. (C) 2011 Elsevier Ltd. All rights reserved.