2-(4-(2-methoxyphenyl)piperazin-1-yl)benzo[d]oxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(4-(2-methoxyphenyl)piperazin-1-yl)benzo[d]oxazole
• 英文别名: 2-[4-(2-Methoxyphenyl)piperazin-1-yl]-1,3-benzoxazole
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: SDQSWBVZTABORA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯苯并恶唑 、 1-(2-甲氧苯基)哌嗪 反应 12.0h， 以86%的产率得到2-(4-(2-methoxyphenyl)piperazin-1-yl)benzo[d]oxazole
  参考文献：
  名称：

  HFIP Promoted Low-Temperature S_NAr of Chloroheteroarenes Using Thiols and Amines

  摘要：

  A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

  DOI：

  10.1021/acs.joc.9b02371

文献信息

• Synthesis of 2-Piperazinylbenzothiazole and 2-Piperazinylbenzoxazole Derivatives with 5-HT3 Antagonist and 5-HT4 Agonist Properties
  作者：Antonio Monge、Maria del Carmen Pena、Juan Antonio Palop、Jose Maria Caldero、Juan Roca、Elisa Garcia、Gonzalo Romero、Joaquin del Rio、Berta Lasheras

  DOI：10.1021/jm00035a012

  日期：1994.4

  New 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives were prepared and tested as 5-HT3 receptor antagonists. Some of the new compounds antagonized the effect of 5-HT at the longitudinal muscle myenteric plexus (LMMP) preparation of the guinea pig ileum, and two benzothiazole derivatives, compounds 2e and 2f, were more potent than ondansetron in this regard. However, these two compounds were much weaker than the typical 5-HT3 receptor antagonist as displacers of [H-3]BRL-43694 binding to rat cerebral cortex homogenates or as antagonists of the bradycardia response to 5-HT in the anaesthetized rat. Like the prokinetic agent cisapride, some of the new compounds enhanced gastric emptying in rats. Compound 2f not only markedly enhanced gastric emptying but was also a potent agonist at the isolated rat oesophageal tunics muscularis mucosae, a preparation sensitive to 5-HT4 receptor stimulation, and enhanced the twitch response in the LMMP preparation. The latter effect was blocked by a high concentration of tropisetron or by previous desensitization with 6-methoxytryptamine Compound 2f appears to show a promising pharmacological profile as a potential gastrokinetic agent.
• HFIP Promoted Low-Temperature S_NAr of Chloroheteroarenes Using Thiols and Amines
  作者：Yuvraj B. Bhujabal、Kamlesh S. Vadagaonkar、Aniket Gholap、Yogesh S. Sanghvi、Rambabu Dandela、Anant R. Kapdi

  DOI：10.1021/acs.joc.9b02371

  日期：2019.12.6

  A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.