(4-dimethylamino-benzylidene)-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine | 61820-63-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (4-dimethylamino-benzylidene)-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine
• CAS: 61820-63-1
• 化学式: C₁₇H₁₆N₄O
• 分子量: 292.34
• InChiKey: HGYQKQBDPOMWTA-UHFFFAOYSA-N

物化性质

• 熔点：
  183.0-185.5 °C
• 沸点：
  472.0±47.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4-dimethylamino-benzylidene)-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine 、 氯乙酸 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4R)-3-Chloro-4-(4-dimethylamino-phenyl)-1-(5-phenyl-[1,3,4]oxadiazol-2-yl)-azetidin-2-one
  参考文献：
  名称：

  Giri, S.; Kumar, Rakesh; Nizamuddin, Agricultural and Biological Chemistry, 1988, vol. 52, # 3, p. 621 - 624

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酸 以 乙醇 为溶剂， 生成 (4-dimethylamino-benzylidene)-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine
  参考文献：
  名称：

  Expeditious Synthesis, Antimicrobial and Antimalarial Activities of Novel Heterocycles Bearing Imidazole-oxadiazole Based Hybrid Pharmacophores

  摘要：

  A facile synthesis of 2-substituted-5-amino-oxadiazole derivatives has been achieved by refluxing/sonicating a mixture of semicarbazide with various aromatic acids in conc. sulphuric acid alone. The isolated products were further condensed with p-dimethylaminobenzaldehyde/p-hydroxybenzaldehyde to obtain respective imino derivatives. Finally, some potentially biologically active imidazole analogues were obtained by reacting ammonium acetate and 5-bromoisatin with the synthesized imino products. All the newly synthesized compounds were thoroughly characterized by standard analytical techniques. These imidazole-oxadiazole hybrid compounds were also evaluated for their antimicrobial and antimalarial activities. The compounds all exhibited moderate to significant antimicrobial activity (6-10mm, zone of inhibition) and promising antimalarial activity (IC50 0.037-0.100 mu M). This report entails a detailed synthetic procedure, spectroscopic elucidation and activities of the synthesized compounds. Supporting Information for this article is available online at http://www.thieme-connect.de/products

  DOI：

  10.1055/s-0042-112028

文献信息

• Addition reactions of heterocumulenes. II. 1,4-Cycloaddition reactions of diphenylketene with azadienes.
  作者：MASANORI SAKAMOTO、KYOKO MIYAZAWA、YOSHIO TOMIMATSU

  DOI：10.1248/cpb.24.2532

  日期：——

  Reaction of diphenylketene (I) with azadienes (II-IX), having -C=N-C=N- multiple bond system between carbon-nitrogen double bond in heterocycles and their side-chain carbon-nitrogen double bond, gave the 1, 4-cycloadducts (XI-XVIII), respectively. Hydrogenolysis of the 1, 4-cycloadducts (XIb, XIIb, and XVIb), with lithium aluminum hydride in tetrahydrofuran gave the 1-propanol derivatives (XIX, XXI, and XXII), respectively. On the other hand, reaction of I with 3-(p-anisylideneamino)-5-phenylisoxazole (Xb) and 2-benzylideneaminopyridine (XXIV) respectively afforded 1-[3-(5-phenylisoxazolyl)]-3, 3-diphenyl-4-(p-anisyl)-2-azetidinone (XXIII) and 1-(2-pyridyl)-3, 3, 4-triphenyl-2-azetidinone (XXV).

  二苯基酮（I）与具有-C=N-C=N-多重键系统的阿扎二烯（II-IX）反应，生成了1,4-环加成物（XI-XVIII）。1,4-环加成物（XIb、XIIb和XVIb）在四氢呋喃中与铝锂氢化物反应进行氢解，分别生成了1-丙醇衍生物（XIX、XXI和XXII）。另一方面，I与3-(对乙氧基苯亚胺基)-5-苯基异噻唑（Xb）和2-苯甲亚胺基吡啶（XXIV）反应，分别得到1-[3-(5-苯基异噻唑基)]-3,3-二苯基-4-(对乙氧基苯基)-2-氮杂环丁酮（XXIII）和1-(2-吡啶基)-3,3,4-三苯基-2-氮杂环丁酮（XXV）。