3-benzyl-5-chloro-1,3-benzoxazol-2(3H)-one | 40888-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-benzyl-5-chloro-1,3-benzoxazol-2(3H)-one
• 英文别名: 3-benzyl-5-chlorobenzoxazol-2(3H)-one；3-benzyl-5-chlorobenzoxazolone；3-Benzyl-5-chloro-1,3-benzoxazol-2-one
• CAS: 40888-04-8
• 化学式: C₁₄H₁₀ClNO₂
• mdl: MFCD08278488
• 分子量: 259.692
• InChiKey: JXJYNDKNKPOGPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 在 sodium tetrahydroborate 、 氯化铵 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 3-benzyl-5-chloro-1,3-benzoxazol-2(3H)-one
  参考文献：
  名称：

  Synthesis of 3-Alkylbenzoxazolones from N-Alkyl-N-arylhydroxylamines by Contiguous O-Trichloroacetylation, Trichloroacetoxy ortho-Shift, and Cyclization Sequence

  摘要：

  Benzoxazolone pharmacophore is present in clinical pharmaceuticals, drug candidates, and many compounds having a wide spectrum of biological activities. The methods available for the synthesis of benzoxazolones have limited diversity due to problems in accessibility and air-sensitivity of diversely substituted o-aminophenols from which they are generally prepared by cyclocarbonylation with phosgene or its equivalents. The present paper describes a mild method for the synthesis of 3-alkylbenzoxazolones from easily accessible and air-stable nitroarenes. Nitroarenes were converted to N-alkyl-N-arylhydroxylamines in two steps involving partial reduction to arylhydroxylamines followed by selective N-alkylation. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields through an uninterrupted three-step sequence involving O-trichloroacetylation, N -> C-ortho trichloroacetoxy shift, and cyclization in a single pot at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups like alkyl and aryl esters, amide, cyano, and the carbon-carbon double bond survive the reaction.

  DOI：

  10.1021/jo401985h

文献信息

• 一种N-苄基苯并噁唑酮类化合物及其合成方 法
  申请人：安徽师范大学

  公开号：CN107188864B

  公开（公告）日：2019-06-04

  本发明提供了一种N‑苄基苯并噁唑酮类化合物及其合成方法，密封空气条件下，无金属催化，苯并噁唑类化合物和甲苯类化合物直接反应制备N‑苄基苯并噁唑酮类化合物，与现有技术相比，本发明合成方法十分简单，方便，原料易得，成本低，效率高，适合多种反应底物。制备的产品可用于临床能够有效治疗疾病的药物及药物中间体。
• 一种N-苄基苯并杂环酮化合物的制备方法
  申请人：湖南科技大学

  公开号：CN115043789B

  公开（公告）日：2023-07-14

  本发明公开了一种N‑苄基苯并杂环酮化合物的制备方法，苯甲醇衍生物与苯并杂环化合物在亚磷酸、碘、碱以及溶剂存在的条件下加热反应，制得N‑苄基苯并杂环酮化合物。本发明选用廉价易得的苯甲醇衍生物为苄基化试剂，以亚磷酸和单质碘为促进剂，在碱存在下，通过与苯并杂环化合物直接反应一锅一步高效实现了N‑苄基苯并杂环酮化合物的制备，具有无需过渡金属，原料廉价易得，底物范围广，绿色环保等优点，避免了使用危险试剂、过渡金属催化剂及多步反应的局限，有利于工业化生产。
• H3PO3/I2 mediated formation of N-benzyl benzo heterocyclic ketones from aromatic aldehydes and benzyl alcohol derivatives
  作者：Xiaoyi Wang、Junchun Xiang、Jie Wang、Zhilan Yu、Zi-Long Tang、Jing Xiao

  DOI：10.1016/j.tet.2022.133094

  日期：2022.11

  We report a H3PO3/I2 mediated formation of N-benzyl benzo heterocyclic ketones from the reaction of benzo heterocyclic compounds with aromatic aldehydes or benzyl alcohol derivatives under metal-free conditions in one-pot. For the first time, aromatic aldehydes were used as benzylated reagents to synthesize benzo heterocyclic ketones in the presence of K2CO3. Control experiments indicated that the

  我们报告了 H 3 PO 3 /I 2介导的N-苄基苯并杂环酮的形成，该反应由苯并杂环化合物与芳香醛或苯甲醇衍生物在无金属条件下在一锅中反应。首次以芳香醛为苄基化试剂在K 2 CO 3存在下合成苯并杂环酮。对照实验表明羰基氧最有可能来源于K 2 CO 3。H 3 PO 3还起到促进剂和氢源的双重作用。这种新方法具有底物范围广、成本低、条件简单等特点。
• CsF–Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)-benzoxazolone derivatives
  作者：M. S. R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav、U. S. N. Murty、K. Pranay Kumar

  DOI：10.1007/s00044-010-9367-5

  日期：2011.6

  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.