5-(4-phenoxyphenyl)-1,3,4-thiadiazol-2-amine | 299442-68-5

• 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: 5-(4-phenoxyphenyl)-1,3,4-thiadiazol-2-amine
• 英文别名: 1,3,4-Thiadiazol-2-amine, 5-(4-phenoxyphenyl)-
• CAS: 299442-68-5
• 化学式: C₁₄H₁₁N₃OS
• 分子量: 269.327
• InChiKey: PAXCUQADIZYNNN-UHFFFAOYSA-N

物化性质

• 沸点：
  452.4±47.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-phenoxyphenyl)-1,3,4-thiadiazol-2-amine 、 肉豆蔻酰氯 在 吡啶 作用下， 反应 4.25h， 生成
  参考文献：
  名称：

  Novel fatty acid‐thiadiazole derivatives as potential antimycobacterial agents

  摘要：

  AbstractThe discovery of antibiotics around the middle twentieth century led to a decrease in the interest in antimycobacterial fatty acids. In order to re‐establish the importance of naturally abundant fatty acid, a series of fatty acid‐thiadiazole derivatives were designed and synthesized based on molecular hybridization approach. In vitro antimycobacterial potential was established by a screening of synthesized compounds against Mycobacterium tuberculosis H37Rv strain. Among them, compounds 5a, 5d, 5h, and 5j were the most active, with compound 5j exhibiting minimum inhibitory concentration of 2.34 μg/ml against M.tb H37Rv. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on enoyl‐acyl carrier protein reductases (InhA), which is involved in the mycobacterium fatty acid biosynthetic pathway.

  DOI：

  10.1111/cbdd.13634
• 作为产物：
  描述：

  苯甲酸苯酯 在 二硫化碳 、 sodium hypobromide 、 一水合肼 、 三氯氧磷 作用下， 以 四氢呋喃 、 二乙二醇 为溶剂， 反应 14.0h， 生成 5-(4-phenoxyphenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis, Insecticidal Evaluation of Novel 1,3,4-Thiadiazole Chrysanthemamide Derivatives formed by an EDCI/HOBt Condensation

  摘要：

  通过 EDCI/HOBt 缩合反应合成了一系列新型杀虫剂，其两种成分分别来自 1,3,4-噻二唑和菊酸。通过红外光谱、1H NMR 和元素分析，确定了这些 1,3,4-噻二唑菊酰胺。同时还对它们的杀虫活性进行了评估。

  DOI：

  10.3184/174751911x13230201951890

文献信息

• Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from <i>N</i>-Tosylhydrazones
  作者：Zeyang Wei、Qi Zhang、Meng Tang、Siyu Zhang、Qian Zhang

  DOI：10.1021/acs.orglett.1c01379

  日期：2021.6.4
• Synthesis and Insecticidal Activities of Novel 1,3,4-Thiadiazole 5-Fluorouracil Acetamides Derivatives: An RNA Interference Insecticide
  作者：Rong Wan、Jian-Qiang Zhang、Fen Han、Peng Wang、Peng Yu、Qiu He

  DOI：10.1080/15257770.2011.580811

  日期：2011.4

  A series of novel 1,3,4-thiadiazole 5-fluorouracil acetamides derivatives were designed and synthesized. Their structures were confirmed by infrared, 1H NMR spectroscopy, and elemental analysis. The insecticidal activities against Tetranychus cinnabarinus and Aphis craccivora of these new compounds were evaluated. The bioassay tests showed that most of these title compounds possessed a good combination of stomach toxicity as well as contact toxicity against Tetranychus cinnabarinus and Aphis craccivora. In particular, the insecticidal activity of the title compound IVe against Aphis craccivora was better than the commercialized thiacloprid and was also comparable to another commercialized product, imidacloprid. The introduction of fluorines to meta and para-position of the benzene ring was essential for high bioactivity.
• US4036826A
  申请人：——

  公开号：US4036826A

  公开（公告）日：1977-07-19
• US4233214A
  申请人：——

  公开号：US4233214A

  公开（公告）日：1980-11-11
• Synthesis, Insecticidal Evaluation of Novel 1,3,4-Thiadiazole Chrysanthemamide Derivatives formed by an EDCI/HOBt Condensation
  作者：Peng Yu、Jun Hu、Tao-Yu Zhou、Peng Wang、Yan-Hua Xu

  DOI：10.3184/174751911x13230201951890

  日期：2011.12

  A series of novel pesticides with two components derived from a 1,3,4-thiadiazole and chrysanthemic acid were synthesised via an EDCI/HOBt condensation. These 1,3,4-thiadiazole chrysanthemamides were identified by IR, ¹H NMR and elemental analyses. Their insecticidal activity was also evaluated.

  通过 EDCI/HOBt 缩合反应合成了一系列新型杀虫剂，其两种成分分别来自 1,3,4-噻二唑和菊酸。通过红外光谱、1H NMR 和元素分析，确定了这些 1,3,4-噻二唑菊酰胺。同时还对它们的杀虫活性进行了评估。