(3β,11bβ)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizin-2-one | 2609-33-8

• 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: (3β,11bβ)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizin-2-one
• 英文别名: (3β,11bβ)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one；(3R,11bR)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
• CAS: 2609-33-8
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: BOBCQOOZINHVMK-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

反应信息

• 作为反应物：
  描述：

  (3β,11bβ)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizin-2-one 在 氨 作用下， 以 乙醇 为溶剂， 生成
  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：

  在 吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二甲基亚砜 、 苯 为溶剂， 以69%的产率得到(3β,11bβ)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizin-2-one
  参考文献：
  名称：

  Ninomiya, Ichiya; Tada, Yukiko; Kiguchi, Toshiko, Journal of the Chemical Society. Perkin transactions I, 1984, p. 2035 - 2038

  摘要：

  DOI：

文献信息

• Asymmetric synthesis of benzoquinolizidines: a formal synthesis of (-)-emetine
  作者：Joseph W. Guiles、A. I. Meyers

  DOI：10.1021/jo00024a032

  日期：1991.11

  Chiral formamidines affixed to tetrahydroisoquinoline derivatives affords the appropriate precursor 9 to various benzo[a]quinolizidines 2 and 3 and dibenzo[a,g]quinolizidines 4 in modest to high optical purity. Both 3 and 4 have been utilized in total syntheses of natural emetine 1, thus the route herein constitutes a formal total synthesis of 1. Furthermore, Mannich cyclizations of 1-alkylisoquinolines 18a-c proceeded with or without loss of absolute stereochemistry at the C-1 position. Explanation for this behavior is based upon whether a [3,3] rearrangement or a Mannich reaction takes place. The former results in virtually complete racemization of 18, whereas the latter totally conserves the chirality in 18. Finally, 1-alkynylisoquinolines of high optical purity were transformed, via the Overman protocol, to alkylidine benzo[a]quinolizidines 24 in good yield and to our knowledge, high enantiomeric excess.
• 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：——
• RUBIRALTA, MARIO;DIEZ, ANNA;BALET, ANTONIA;BOSCH, JOAN, TETRAHEDRON, 43,(1987) N 13, 3021-3030
  作者：RUBIRALTA, MARIO、DIEZ, ANNA、BALET, ANTONIA、BOSCH, JOAN

  DOI：——

  日期：——
• BALL, JONACHAN B.;BREEER, JOHN B.;BROWNE, ELAINE J., HETEROCYCLES, 26,(1987) N 6, C. 1573-1580
  作者：BALL, JONACHAN B.、BREEER, JOHN B.、BROWNE, ELAINE J.

  DOI：——

  日期：——
• 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.