12-trans-3-ethyl-3,4,6,7-tetrahydro-1H-[1,3]dioxolo[4,5-g]pyrido[2,1-a]isoquinolin-2(12bH)-one | 86457-19-4

• 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: 12-trans-3-ethyl-3,4,6,7-tetrahydro-1H-[1,3]dioxolo[4,5-g]pyrido[2,1-a]isoquinolin-2(12bH)-one
• CAS: 86457-19-4
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: RMOXKLVTNUZPKF-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  12-trans-3-ethyl-3,4,6,7-tetrahydro-1H-[1,3]dioxolo[4,5-g]pyrido[2,1-a]isoquinolin-2(12bH)-one 在 potassium tert-butylate 、 氨 作用下， 以 乙醇 为溶剂， 生成 (2R,3S,12bS)-3-ethylspiro[1,3,4,6,7,12b-hexahydro-[1,3]benzodioxolo[6,5-a]quinolizine-2,5'-1,3-oxazolidine]-2'-one
  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
• 作为产物：
  描述：

  3-亚甲基-2-戊酮 、 7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride 反应 1.5h， 生成 12-trans-3-ethyl-3,4,6,7-tetrahydro-1H-[1,3]dioxolo[4,5-g]pyrido[2,1-a]isoquinolin-2(12bH)-one
  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

• Redox-Annulation of Cyclic Amines and β-Ketoaldehydes
  作者：Weijie Chen、Daniel Seidel

  DOI：10.1021/acs.orglett.6b00151

  日期：2016.3.4

  Benzo[a]quinolizine-2-one derivatives are readily assembled from 1,2,3,4-tetrahydroisoquinoline and β-ketoaldehydes by means of a new intramolecular redox-Mannich process. These reactions are promoted by simple acetic acid and are thought to involve azomethine ylides as reactive intermediates.

  通过新的分子内氧化还原-曼尼希方法，可以容易地将1,2,3,4-四氢异喹啉和β-酮醛组装成苯并[ a ]喹啉嗪-2-酮衍生物。这些反应通过简单的乙酸促进，并被认为涉及偶氮甲亚胺作为反应性中间体。