11-trans-3-butyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one | 86457-13-8

• 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: 11-trans-3-butyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one
• 英文别名: (+/-)-3c-butyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one；(+/-)-3c-Butyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isochinolin-2-on；(3S,11bS)-3-butyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
• CAS: 86457-13-8
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: CXDIPZOEHIFPBF-HOCLYGCPSA-N

物化性质

• 沸点：
  454.1±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  11-trans-3-butyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one 在 potassium tert-butylate 、 氨 作用下， 以 乙醇 为溶剂， 生成 (2R,3S,11bS)-3-butyl-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：

  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：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium ethanolate 、 甲苯 作用下， 生成 11-trans-3-butyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one
  参考文献：
  名称：

  Brossi et al., Helvetica Chimica Acta, 1958, vol. 41, p. 119,129

  摘要：

  DOI：

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。
• Syntheseversuche in der Emetin-Reihe. 4. Mitteilung. Racemisches 2-Dehydro-emetin
  作者：A. Brossi、M. Baumann、L. H. Chopard-dit-Jean、J. Würsch、F. Schneider、O. Schnider

  DOI：10.1002/hlca.19590420319

  日期：——

  Rac. 2-dehydro-emetine (XV) and rac. 2-dehydro-isoemetine (XVI) have been synthesized in five steps and in good yield from 2-oxo-3-ethyl-9,10-dimethoxy-l, 2,3, 4,6,7-hexahydro-11bH-benzo [a]chinolizine (VII). Homologues and analogues of XV and XVI with other substituents have been obtained in the same way.

  Rac。2-脱氢-依替丁（XV）和rac。由2-氧代-3-乙基-9,10-二甲氧基-1,2,3,4,6,7-六氢-11bH-苯并五步合成2-脱氢异异丁胺（XVI），收率高[a]喹诺酮（VII）。XV和XVI与其他替代物的同系物和类似物已经以相同的方式获得。
• Syntheseversuche in der Emetin-Reihe. 3. Mitteilung. 2-Hydroxy-hydrobenzo[a]chinolizine
  作者：A. Brossi、L. H. Chopard-dit-Jean、O. Schnider

  DOI：10.1002/hlca.19580410634

  日期：——

  The reduction of various 2-oxo-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizines substituted in 3-position is described. Depending upon the method of reduction and the experimental conditions applied, either a sterically homogeneous carbinol or a mixture of two epimeric carbinols is obtained. Their stereochemistry is discussed. Various derivatives of these alcohols are described.

  描述了在3-位上取代的各种2-氧代-1,2,3,4,6,7-六氢-11b H-苯并[a]喹喔啉的还原。取决于还原方法和所应用的实验条件，可获得空间均一的甲醇或两种差向异构的甲醇的混合物。他们的立体化学进行了讨论。描述了这些醇的各种衍生物。
• US2877226
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