9-Azapentacyclo[15.2.2.02,16.03,8.010,15]henicosa-2(16),3,5,7,10,12,14,18-octaene | 134310-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 9-Azapentacyclo[15.2.2.02,16.03,8.010,15]henicosa-2(16),3,5,7,10,12,14,18-octaene
• CAS: 134310-86-4
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: VHJYEXONFVQWNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-acetyl-10-bromo-5H-dibenz[b,f]azepine 在 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 9-Azapentacyclo[15.2.2.02,16.03,8.010,15]henicosa-2(16),3,5,7,10,12,14,18-octaene
  参考文献：
  名称：

  Preparation of 9H-tribenz[b,d,f]azepine and its 1-methoxy derivative

  摘要：

  Two convenient routes to 9H-tribenz[b,d,f]azepine (2) have been developed. The first method involves the deoxygenation and hydrolysis of 1,4-dihydro-1,4-epoxy-9-acetyl-9H-tribenz[b,d,f]azepine (8) employing low-valent titanium. The second method employs the reactive intermediate 10,11-didehydro-5-acetyl-5H-dibenz[b,f]azepine (7) in a Diels-Alder reaction with 1,3-cyclohexadiene. The resulting cycloadduct 13 upon undergoing a retro-Diels-Alder reaction and hydrolysis yields 2. 1-Methoxy-9H-tribenz[b,d,f]azepine (11) was prepared from ring opening of 8 to 1-hydroxy-9-acetyl-9H-tribenz[b,d,f]azepine (10) followed by methylation with dimethyl sulfate and hydrolysis.

  DOI：

  10.1021/jo00012a023

文献信息

• AXTELL, HOLLY C.;, HOWELL WILLIAM M.;SCHMID, LAWRENCE G.;CANN, MICHAEL C., J. ORG. CHEM., 56,(1991) N2, C. 3906-3908
  作者：AXTELL, HOLLY C.、, HOWELL WILLIAM M.、SCHMID, LAWRENCE G.、CANN, MICHAEL C.

  DOI：——

  日期：——
• Preparation of 9H-tribenz[b,d,f]azepine and its 1-methoxy derivative
  作者：Holly C. Axtell、William M. Howell、Lawrence G. Schmid、Michael C. Cann

  DOI：10.1021/jo00012a023

  日期：1991.6

  Two convenient routes to 9H-tribenz[b,d,f]azepine (2) have been developed. The first method involves the deoxygenation and hydrolysis of 1,4-dihydro-1,4-epoxy-9-acetyl-9H-tribenz[b,d,f]azepine (8) employing low-valent titanium. The second method employs the reactive intermediate 10,11-didehydro-5-acetyl-5H-dibenz[b,f]azepine (7) in a Diels-Alder reaction with 1,3-cyclohexadiene. The resulting cycloadduct 13 upon undergoing a retro-Diels-Alder reaction and hydrolysis yields 2. 1-Methoxy-9H-tribenz[b,d,f]azepine (11) was prepared from ring opening of 8 to 1-hydroxy-9-acetyl-9H-tribenz[b,d,f]azepine (10) followed by methylation with dimethyl sulfate and hydrolysis.