2-tert-butyl-5-(4'-nitrophenyl)-1,3,4-oxadiazole | 75655-57-1

• 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-tert-butyl-5-(4'-nitrophenyl)-1,3,4-oxadiazole
• 英文别名: 2-Tert-butyl-5-(4-nitrophenyl)-1,3,4-oxadiazole
• CAS: 75655-57-1
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: VJMXBOYVKHDVPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-tert-butyl-5-(4'-nitrophenyl)-1,3,4-oxadiazole 在 sodiumsulfide nonahydrate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.75h， 以79%的产率得到5-(4'-aminophenyl)-5-tert-butyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

  摘要：

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.013
• 作为产物：
  描述：

  4-硝基苯酰肼 在 四溴化碳 、 三苯基膦 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 2-tert-butyl-5-(4'-nitrophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  由羧酸和酰肼轻度高效地一锅合成1,3,4-恶二唑

  摘要：

  据报道，一种方便的一锅法从酸和酰基酰肼合成2，5-二取代的1,3,4-恶二唑。用CDI进行酸活化，然后与所需的酰肼偶联，并在同一罐中用Ph 3 P和CBr 4脱水，得到相应的1,3,4-恶二唑，收率很高。给出了酸和酰肼组分的范围。

  DOI：

  10.1016/j.tetlet.2006.05.051

文献信息

• A mild and efficient one pot synthesis of 1,3,4-oxadiazoles from carboxylic acids and acyl hydrazides
  作者：Hemaka A. Rajapakse、Hong Zhu、Mary Beth Young、Bryan T. Mott

  DOI：10.1016/j.tetlet.2006.05.051

  日期：2006.7

  A convenient one pot method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from acids and acyl hydrazides is reported. Acid activation with CDI, followed by coupling with the desired acylhydrazide and dehydration in the same pot with Ph3P and CBr4 affords the corresponding 1,3,4-oxadiazoles in good yield. The scope of the acid and acylhydrazide components is presented.

  据报道，一种方便的一锅法从酸和酰基酰肼合成2，5-二取代的1,3,4-恶二唑。用CDI进行酸活化，然后与所需的酰肼偶联，并在同一罐中用Ph 3 P和CBr 4脱水，得到相应的1,3,4-恶二唑，收率很高。给出了酸和酰肼组分的范围。
• Rigo, Benoit; Cauliez, Pascal, Synthetic Communications, 1988, vol. 18, # 11, p. 1247 - 1252
  作者：Rigo, Benoit、Cauliez, Pascal

  DOI：——

  日期：——
• Rigo, Benoit; Fasseur, Dominique; Cauliez, Pascal, Synthetic Communications, 1989, vol. 19, # 13-14, p. 2321 - 2336
  作者：Rigo, Benoit、Fasseur, Dominique、Cauliez, Pascal、Couturier, Daniel

  DOI：——

  日期：——
• RIGO, BENOLT;CAULIEZ, PASCAL, SYNTH. COMMUN., 18,(1988) N 11, C. 1247-1251
  作者：RIGO, BENOLT、CAULIEZ, PASCAL

  DOI：——

  日期：——
• Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides
  作者：Daniel Conole、Thorsten M. Beck、Morgan Jay-Smith、Malcolm D. Tingle、Charles T. Eason、Margaret A. Brimble、David Rennison

  DOI：10.1016/j.bmc.2014.02.013

  日期：2014.4

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.