7-methoxy-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one | 712-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-methoxy-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one
• 英文别名: 7-methoxy-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one；7-Methoxy-2,3-dihydro-4H-<1,4>-benzoxazepin-5-on；7-Methoxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one；7-methoxy-3,4-dihydro-2H-1,4-benzoxazepin-5-one
• CAS: 712-26-5
• 化学式: C₁₀H₁₁NO₃
• mdl: MFCD14281862
• 分子量: 193.202
• InChiKey: JYJKFOYXMJBNJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  7-methoxy-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one 在 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 7-(hexyloxy)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one
  参考文献：
  名称：

  Synthesis and evaluation of 7-substituted-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones as anticonvulsant and hypnotic agents

  摘要：

  A series of 7-substituted-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones was synthesized. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock (MES) test and a rotated test in mice, respectively. Most of the compounds prepared exhibited anticonvulsant activities in the MES test, 7-(heptyloxy)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (10) was the most active. In the anti-MES potency test, it showed a median effective dose (ED50) of 19.0 mg/kg. The hypnotic effect of the compound 10 was initially investigated by using a pentobarbital-induced-sleep test. Middle (30 mg/kg) and high doses (60 mg/kg) of the compound 10 both significantly increased the pentobarbital-induced sleep from 20.9 +/- A 5.28 to 26.9 +/- A 6.14 and 45.67 +/- A 7.94 min, respectively.

  DOI：

  10.1007/s00044-010-9434-y
• 作为产物：
  描述：

  6-methoxychroman-4-one oxime 在 polyphosphoric acid 作用下， 反应 4.0h， 以62%的产率得到7-methoxy-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one
  参考文献：
  名称：

  Synthesis and evaluation of 7-substituted-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones as anticonvulsant and hypnotic agents

  摘要：

  A series of 7-substituted-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones was synthesized. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock (MES) test and a rotated test in mice, respectively. Most of the compounds prepared exhibited anticonvulsant activities in the MES test, 7-(heptyloxy)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (10) was the most active. In the anti-MES potency test, it showed a median effective dose (ED50) of 19.0 mg/kg. The hypnotic effect of the compound 10 was initially investigated by using a pentobarbital-induced-sleep test. Middle (30 mg/kg) and high doses (60 mg/kg) of the compound 10 both significantly increased the pentobarbital-induced sleep from 20.9 +/- A 5.28 to 26.9 +/- A 6.14 and 45.67 +/- A 7.94 min, respectively.

  DOI：

  10.1007/s00044-010-9434-y

文献信息

• The synthesis and proton magnetic resonance spectra of 2,3-dihydro-1,4-benzoxazepin-5(4H)-ones
  作者：G. S. Sidhu、G. Thyagarajan、U. T. Bhalerao

  DOI：10.1039/j39660000969

  日期：——

  4-benzoxazepin-5(4H)-ones carrying substituents in the aromatic ring have been synthesised. The parent compound has also been prepared in considerably better yields than reported by earlier workers. P.m.r. spectra have been used to distinguish between the isomeric 1,4- and 1,5-benzoxazepin-ones.

  合成了在芳族环中带有取代基的八个2，3-二氢-1，4-苯并恶唑啉-5（4 H）-1 。母体化合物的制备也比早期工人报告的产率要好得多。Pmr光谱已用于区分异构体1,4-和1,5-苯并恶嗪-酮。
• Design and synthesis of 10-alkoxy-5, 6-dihydro-triazolo[4,3-d]benzo[f][1,4]oxazepine derivatives with anticonvulsant activity
  作者：Xian-Qing Deng、Cheng-Xi Wei、Fu-Nan Li、Zhi-Gang Sun、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2010.03.041

  日期：2010.7

  A series of novel 10-alkoxy-5, 6-dihydro-triazolo[4,3-d]enzo[f][1,4]oxazepine derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). In the MES test, compound 10-Heptyloxy-5, 6-dihydro-triazolo[4,3-d]benzo[f][1,4]oxazepine (8f) was found to possess better anticonvulsant activity and higher safety than marketed drugs carbamazepine and phenytoin with an ED50 value of 6.9 mg/kg a PI value of 9.5. To explain the possible mechanism of anticonvulsant activity, compound 8f was tested in pentylenetetrazole, isoniazid, thiosemicarbazide, 3-mercaptopropionic acid and Bicuculline induced seizures tests. The results suggest that compound 8f exerts anticonvulsant activity through GABA-mediated mechanism. (c) 2010 Elsevier Masson SAS. All rights reserved.
• 200. The preparation of some 2,3-dihydro-1,4-benzoxazepin-5(4H)-ones and related compounds
  作者：D. Huckle、I. M. Lockhart、M. Wright

  DOI：10.1039/jr9650001137

  日期：——
• Synthesis and evaluation of 7-substituted-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones as anticonvulsant and hypnotic agents
  作者：Xian-Qing Deng、Ming-Xia Song、Cheng-Xi Wei、Zhi-Gang Sun、Zhe-Shan Quan

  DOI：10.1007/s00044-010-9434-y

  日期：2011.9

  A series of 7-substituted-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones was synthesized. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock (MES) test and a rotated test in mice, respectively. Most of the compounds prepared exhibited anticonvulsant activities in the MES test, 7-(heptyloxy)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (10) was the most active. In the anti-MES potency test, it showed a median effective dose (ED50) of 19.0 mg/kg. The hypnotic effect of the compound 10 was initially investigated by using a pentobarbital-induced-sleep test. Middle (30 mg/kg) and high doses (60 mg/kg) of the compound 10 both significantly increased the pentobarbital-induced sleep from 20.9 +/- A 5.28 to 26.9 +/- A 6.14 and 45.67 +/- A 7.94 min, respectively.