1-cyano-5,6-(methylenedioxy)tetralin | 102035-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-cyano-5,6-(methylenedioxy)tetralin
• 英文别名: 1-Cyano-5,6-methylenedioxy-(1,2,3,4-tetrahydronaphthalene)；6,7,8,9-Tetrahydrobenzo[g][1,3]benzodioxole-6-carbonitrile
• CAS: 102035-30-3
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: WIBFBQHDVFCSHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyano-5,6-(methylenedioxy)tetralin 在 盐酸 、 lithium diisopropyl amide 作用下， 反应 1.5h， 生成 1-(2-imidazolinyl)-1-methyl-5,6-(methylenedioxy)tetralin
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of .alpha.1 and .alpha.2 adrenergic activities

  摘要：

  A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.

  DOI：

  10.1021/jm00158a016
• 作为产物：
  描述：

  5,6-亚甲基二氧基-1-四酮 在 sodium tetrahydroborate 、 三氯化铝 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 、 苯 为溶剂， 反应 3.25h， 生成 1-cyano-5,6-(methylenedioxy)tetralin
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of .alpha.1 and .alpha.2 adrenergic activities

  摘要：

  A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.

  DOI：

  10.1021/jm00158a016

文献信息

• Adrenergic compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0166937B1

  公开（公告）日：1991-08-28
• DEBERNARDIS J. F.; WINN M.; ARENDSEN D. L.; KERKMAN D. J.; KYNCL J. J., J. MED. CHEM., 29,(1986) N 8, 1413-1417
  作者：DEBERNARDIS J. F.、 WINN M.、 ARENDSEN D. L.、 KERKMAN D. J.、 KYNCL J. J.

  DOI：——

  日期：——
• US4634705A
  申请人：——

  公开号：US4634705A

  公开（公告）日：1987-01-06
• Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of .alpha.1 and .alpha.2 adrenergic activities
  作者：John F. DeBernardis、Martin Winn、David L. Arendsen、Daniel J. Kerkman、John J. Kyncl

  DOI：10.1021/jm00158a016

  日期：1986.8

  A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.