cis-(+/-)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido<4,3b>indole | 103383-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: cis-(+/-)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido<4,3b>indole
• 英文别名: cis-(+/-)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3b]indole；(4aR,9bS)-5-phenyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole
• CAS: 103383-85-3
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: CJWPRFAPIUPOSX-NVXWUHKLSA-N

物化性质

• 沸点：
  391.0±41.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-(+/-)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido<4,3b>indole 在 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 cis-(+/-)-5-(4-fluorophenyl)-2-<4-hydroxy-4-(4-fluorophenyl)butyl>-2,3,4,4a,5,9b-hexahydro-1H-pyrido<4,3b>indole
  参考文献：
  名称：

  Neuroleptics from the 4a,9b-cis- and 4a,9b-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole series. 2

  摘要：

  Compounds derived from 4a,9b-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4, 3-b]indole are consistently efficacious in displacing [3H]spiroperidol from striatal dopamine receptors in vitro. Derivatives bearing substituents at position 2, particularly those derived from butyrophenone moieties, are exceptionally potent in vivo. Compounds from the corresponding 4a,9b-cis series are substantially less potent in both in vivo and in vitro assays of neuroleptic activity. Although the cis and trans derivatives have, in some conformations, similar basic nitrogen atom to aromatic ring separations of about 5.1 A, the distance at which the basic nitrogen atom lies above or below the plane of the aromatic ring differs substantially between the two series. Consideration of these results in terms of this and earlier work indicates that the out-of-plane distance for the basic nitrogen in neuroleptic molecules may range from about 0 to about 0.90 A but may be optimized at about 0.55 A.

  DOI：

  10.1021/jm00160a050
• 作为产物：
  描述：

  cis-(+/-)-2-benzyl-5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido<4,3b>indole 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 55.0 ℃ 、379.21 kPa 条件下， 反应 6.0h， 以71%的产率得到cis-(+/-)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido<4,3b>indole
  参考文献：
  名称：

  Neuroleptics from the 4a,9b-cis- and 4a,9b-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole series. 2

  摘要：

  Compounds derived from 4a,9b-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4, 3-b]indole are consistently efficacious in displacing [3H]spiroperidol from striatal dopamine receptors in vitro. Derivatives bearing substituents at position 2, particularly those derived from butyrophenone moieties, are exceptionally potent in vivo. Compounds from the corresponding 4a,9b-cis series are substantially less potent in both in vivo and in vitro assays of neuroleptic activity. Although the cis and trans derivatives have, in some conformations, similar basic nitrogen atom to aromatic ring separations of about 5.1 A, the distance at which the basic nitrogen atom lies above or below the plane of the aromatic ring differs substantially between the two series. Consideration of these results in terms of this and earlier work indicates that the out-of-plane distance for the basic nitrogen in neuroleptic molecules may range from about 0 to about 0.90 A but may be optimized at about 0.55 A.

  DOI：

  10.1021/jm00160a050