(2R,11bS)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane] | 83917-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (2R,11bS)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane]
• CAS: 83917-83-3；83917-84-4
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: GYKMHOQTBMONGT-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  34.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,11bS)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane] 、 氨 、 甲醇 、 N,N'-羰基二咪唑 、 potassium tert-butylate 生成 (2R,11bS)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,5'-1,3-oxazolidine]-2'-one
  参考文献：
  名称：

  DAVIS, R.;KLUGE, A. F.;MADDOX, M. L.;SPARACINO, M. L., J. ORG. CHEM., 1983, 48, N 2, 255-259

  摘要：

  DOI：
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉盐酸盐 反应 1.5h， 生成 (2R,11bS)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane]
  参考文献：
  名称：

  Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s

  摘要：

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.

  DOI：

  10.1021/jm00364a013

文献信息

• Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s
  作者：Joan M. Caroon、Robin D. Clark、Arthur F. Kluge、Chi Ho Lee、Arthur M. Strosberg

  DOI：10.1021/jm00364a013

  日期：1983.10

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.
• DAVIS, R.;KLUGE, A. F.;MADDOX, M. L.;SPARACINO, M. L., J. ORG. CHEM., 1983, 48, N 2, 255-259
  作者：DAVIS, R.、KLUGE, A. F.、MADDOX, M. L.、SPARACINO, M. L.

  DOI：——

  日期：——