(E)-ethyl 3-oxo-7-phenyl-2,3-dihydrobenzo[b]oxepine-4-carboxylate | 1513925-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-ethyl 3-oxo-7-phenyl-2,3-dihydrobenzo[b]oxepine-4-carboxylate
• CAS: 1513925-17-1
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: QCXUSWNUROWMMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-oxo-7-phenyl-2,3-dihydrobenzo[b]oxepine-4-carboxylate 在 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到6-phenyl-3H,10H-benzo[6,7]oxepino[3,4-c]isoxazol-3-one
  参考文献：
  名称：

  Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones

  摘要：

  Series of new benzoxepinoisoxazolones 4a-d and pyrazolones 6a-t were prepared by the cyclocondensation of substituted (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3a-d with hydroxylamine hydrochloride and phenylhydrazine hydrochlorides 5a-k. Synthesized compounds were screened for their in vitro anti-mycobacterial activity and anticancer activity. Ten compounds displayed good anti-mycobacterial activity, among these; compound 4d and 6b found to be potent when compared to standard drug isoniazid. Eleven compounds displayed good anticancer activity and compounds 4b-d displayed equipotent activity on HeLa cell lines when compared to standard drug doxorubicin. Activation of caspase-3 and caspase-9 has been measured for compounds 4b-d on HeLa cell lines (apoptosis). This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of benzoxepinoisoxazolones and pyrazolones. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.042
• 作为产物：
  描述：

  2-hydroxy-5-phenylbenzaldehyde 在 哌啶 、 乙氧甲酰基亚乙基三苯基 作用下， 以 二氯甲烷 为溶剂， 反应 14.25h， 生成 (E)-ethyl 3-oxo-7-phenyl-2,3-dihydrobenzo[b]oxepine-4-carboxylate
  参考文献：
  名称：

  Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones

  摘要：

  Series of new benzoxepinoisoxazolones 4a-d and pyrazolones 6a-t were prepared by the cyclocondensation of substituted (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3a-d with hydroxylamine hydrochloride and phenylhydrazine hydrochlorides 5a-k. Synthesized compounds were screened for their in vitro anti-mycobacterial activity and anticancer activity. Ten compounds displayed good anti-mycobacterial activity, among these; compound 4d and 6b found to be potent when compared to standard drug isoniazid. Eleven compounds displayed good anticancer activity and compounds 4b-d displayed equipotent activity on HeLa cell lines when compared to standard drug doxorubicin. Activation of caspase-3 and caspase-9 has been measured for compounds 4b-d on HeLa cell lines (apoptosis). This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of benzoxepinoisoxazolones and pyrazolones. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.042

文献信息

• A Novel Approach for C–C, C–N, and C–O Bond Formation Reactions: A Facile Synthesis of Benzophenazine, Quinoxaline, and Phenoxazine Derivatives via Ring Opening of Benzoxepines
  作者：Bhimapaka China Raju、Kasagani Veera Prasad、Gannerla Saidachary、Balasubramanian Sridhar

  DOI：10.1021/ol4033122

  日期：2014.1.17

  synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives by the reaction of benzoxepine-4-carboxylates with benzene-1,2-diamines, ethane-1,2-diamine, and 2-aminophenols in the presence of Bi(OTf)3 (5 mol %) under mild conditions in very good yields. The present protocol opens a new way for C–C, C–N, and C–O bond-formation reactions in a single-step process. The structural assignment was

  已开发出一种新的一锅操作规程，用于通过苯并氧杂庚酸酯-4-羧酸盐与苯-1,2-二胺，乙烷-1,2-二胺和2-氨基苯酚的反应来合成苯并吩嗪，喹喔啉和苯恶嗪衍生物在温和的条件下在Bi（OTf）3（5 mol％）存在下以非常好的收率。本协议为单步过程中C–C，C–N和C–O键形成反应开辟了一条新途径。通过X射线分析确认了结构分配。
• A facile construction of oxygen heterocycles by the reaction of benzoxepine-4-carboxylates with dihaloalkanes and activated alkynes
  作者：Veera Prasad Kasagani、Siva Hariprasad Kurma、China Raju Bhimapaka

  DOI：10.1039/c9ob00769e

  日期：——

  This manuscript describes the preparation of heterocyclic compounds such as naphtho[1,3]-dioxoles (3a-h), [1,4]-dioxines (4a-h), [1,4]-dioxepines (5a-c), [1,4]-dioxocines (6a-c) and diethyl 2-(2-ethoxy-2-oxoethyl)naphtho[1,3]dioxoles (8a-f). These heterocyclic compounds have been achieved by the reaction of benzoxepine-4-carboxylates (1a-h) with dihaloalkanes (2a-e) and activated alkyne (7a) for the

  该手稿描述了杂环化合物的制备，例如萘并[1,3]-二恶唑（3a-h），[1,4]-二恶英（4a-h），[1,4]-二氧杂庚环（5a-c）， [1，4]-二氧杂环酮（6a-c）和2-（2-乙氧基-2-氧代乙基）萘二乙基[1，3]二恶唑（8a-f）。这些杂环化合物是通过苯并xepine-4-羧酸盐（1a-h）与二卤代烷烃（2a-e）和活化炔烃（7a）的首次反应获得的。这项工作代表了通过一步法形成CC和CO键来构建实用氧杂环的第一个例子。