2-[4-(1,3-benzoxazol-2-yl)piperazine-1-yl]ethanol | 159731-49-4

• 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-(1,3-benzoxazol-2-yl)piperazine-1-yl]ethanol
• 英文别名: 2-(4-(benzoxazol-2-yl)piperazin-1-yl)ethanol；2-[4-(2-Hydoxyethyl)-1-piperazinyl]benzoxazole；2-[4-(1,3-benzoxazol-2-yl)piperazin-1-yl]ethanol
• CAS: 159731-49-4
• 化学式: C₁₃H₁₇N₃O₂
• mdl: MFCD02931133
• 分子量: 247.297
• InChiKey: SCVGHKHLYYNGSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-巯基苯并恶唑 在 五氯化磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 2-[4-(1,3-benzoxazol-2-yl)piperazine-1-yl]ethanol
  参考文献：
  名称：

  CsF–Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)-benzoxazolone derivatives

  摘要：

  The synthesis and antimicrobial activity studies of a new series of cyclic amine containing benzoxazoles and benzoxazolone-2(3H)-ones derivatives were described. The alkylation of benzoxazolone was carried out using cesium fluoride-Celite. The newly synthesized compounds with the influence of the induction of the cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to the antibacterial and antifungal activity. The 2-cyclic amine-1,3-benzoxazoles (5a-l), 5-chloro-3-alkyl substituted-1,3-benzoxazol-2(3H)-ones (8a-f), and 3-[3-(cyclic amine)propyl]-1,3-benzoxazol-2(3H)-ones (9a-f) were synthesized. These derivatives were tested for antibacterial and antifungal activity. Among the compounds tested, 8c and 9f showed moderate to good antibacterial and antifungal activity. Compound 8a showed good antifungal activity.

  DOI：

  10.1007/s00044-010-9367-5

文献信息

• A Metal-Free Amination of Benzoxazoles – The First Example of an Iodide-Catalyzed Oxidative Amination of Heteroarenes
  作者：Tanja Froehr、Christian P. Sindlinger、Ulrich Kloeckner、Peter Finkbeiner、Boris J. Nachtsheim

  DOI：10.1021/ol201439t

  日期：2011.7.15

  An efficient transition-metal-free amination of benzoxazoles has been developed. With catalytic amounts of tetrabutylammoniumiodide (TBAI), aqueous solutions of H2O2 or TBHP as co-oxidant and under mild reaction conditions, highly desirable 2-aminobenzoxazoles were isolated in excellent yields of up to 93%. First mechanistic experiments indicate the in situ iodination of the secondary amine as the

  已经开发出有效的无过渡金属苯并恶唑胺化的方法。用催化量的四丁基碘化铵（TBAI），H 2 O 2或TBHP水溶液作为助氧化剂，并在温和的反应条件下，以高达93％的优异收率分离出了非常理想的2-氨基苯并恶唑。最初的机械实验表明，仲胺的原位碘化是假定的活化方式。
• Efficient and Novel Synthesis of Benzoxazole Derivatives in the Presence of Zinc Dust Under Solvent-Free Conditions
  作者：M. S. R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav

  DOI：10.1080/00397910903320621

  日期：2010.8.31

  A mild and efficient method has been developed for the synthesis of 2-cyclic amine-substituted benzoxazole derivatives using zinc dust under microwave irradiation in the absence of solvent is described. A comparative study was performed under conventional and microwave heating conditions. Zinc dust can be reused several times after reactivation. The significant feature of this method is the isolation

  描述了一种温和有效的方法，用于在没有溶剂的情况下在微波辐射下使用锌粉合成 2-环胺取代的苯并恶唑衍生物。在常规和微波加热条件下进行了比较研究。锌粉在重新激活后可以重复使用多次。该方法的显着特点是在较短的反应时间内通过简单的后处理分离出高纯度的纯产品。
• Benzoxazole derivatives
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：US05631257A1

  公开（公告）日：1997-05-20

  A benzoxazole derivative of the formula (1) or (2) which has an alicyclic diamine group at the 2-position: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X.sup.-, m and n are defined herein. The compound shows excellent 5-HT.sub.3 receptor antagonism and is useful as an antiemetic agent, a peristalsis controlling agent, an analgesic agent, an antianxiety agent and a schizophrenia treating agent.

  公式（1）或（2）的苯并噁唑衍生物，在2-位置具有脂环型二胺基团：##STR1## 其中R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，R.sup.6，X.sup.-，m和n在此定义。该化合物表现出优异的5-HT.sub.3受体拮抗作用，可用作止吐剂、控制肠蠕动剂、镇痛剂、抗焦虑剂和治疗精神分裂症的药物。
• Benzoxazole derivatives and their use as serotonin 5-HT3 receptor antagonists
  申请人：MEIJI SEIKA KAISHA LTD.

  公开号：EP0621271A1

  公开（公告）日：1994-10-26

  A benzoxazole derivative of the formula (1) or (2) which has an alicyclic diamine group at the 2-position: wherein R¹, R², R³ and R⁴ may be the same or different and each represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkenyl, halogen, hydroxyl, amino, lower alkoxy, carboxyl, carbamoyl and nitro, or any two of R¹ to R⁴ may be linked together to form a three to seven-membered ring structure comprising carbon atoms alone or carbon atoms and 1 to 2 hetero atoms, which may be substituted; R⁵ and R⁶ may be the same or different and each represents substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkenyl, substituted or unsubstituted aralkyl group or an alkoxycarbonyl group, or R⁵ and R⁶ may be linked together to form a three to seven-membered ring structure comprising carbon atoms and 1 to 2 nitrogen atoms, which may be substituted; X⁻ is a pharmaceutically acceptable anion; and m and n may be the same or different and each is an integer of 1 to 3. The compound shows excellent 5-HT₃ receptor antagonism and is useful as an antiemetic agent and also as a peristalsis controlling agent, an analgesic agent, an antianxiety agent and a schizophrenia treating agent.

  式（1）或（2）的苯并恶唑衍生物，其 2 位上有脂环二胺基团： 其中 R¹、R²、R³ 和 R⁴ 可以相同或不同，各自代表氢、取代或未取代的低级烷基、取代或未取代的低级烯基、卤素、羟基、氨基、低级烷氧基、羧基、氨基甲酰基和硝基，或者 R¹ 至 R⁴ 中的任意两个可以连接在一起，形成由单独的碳原子或碳原子和 1 至 2 个杂原子组成的三至七元环结构，这些杂原子可以被取代；R⁵和R⁶可以相同或不同，并且各自代表取代或未取代的低级烷基、取代或未取代的低级烯基、取代或未取代的芳烷基或烷氧基羰基，或者R⁵和R⁶可以连接在一起形成由碳原子和 1 至 2 个氮原子组成的三至七元环结构，该结构可以被取代；X- 是药学上可接受的阴离子；m 和 n 可以相同或不同，且各自为 1 至 3 的整数。该化合物具有优异的 5-HT₃ 受体拮抗作用，可用作止吐药，也可用作肠蠕动控制剂、镇痛剂、抗焦虑剂和精神分裂症治疗剂。
• US5631257A
  申请人：——

  公开号：US5631257A

  公开（公告）日：1997-05-20