(Z)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one | 654645-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
• 英文别名: (Z)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one；(2Z)-2-[[1-(benzenesulfonyl)indol-3-yl]methylidene]-1-azabicyclo[2.2.2]octan-3-one
• CAS: 654645-01-9
• 化学式: C₂₂H₂₀N₂O₃S
• 分子量: 392.478
• InChiKey: CUUOJXHVTOJHCZ-STZFKDTASA-N

物化性质

• 沸点：
  652.5±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol
  参考文献：
  名称：

  (Z)-2-(1-Phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one and (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol

  摘要：

  The title compounds, C22H20N2O3S, ( I), and C22H22N2O3S, (II), crystallize in space groups P(1) over bar and P2(1)2(1)2(1), respectively. The indole rings are planar and the benzene ring of the phenylsulfonyl group makes a dihedral angle with the mean plane of the indole ring of 90.2 (2)degrees in (I) and 94.0 (2)degrees in (II). In both molecules, the double bond connecting the azabicyclic and indole moieties has a Z geometry. Compound (II) was obtained as an enantiomerically pure crystal and has the 3S configuration.

  DOI：

  10.1107/s0108270104015847
• 作为产物：
  描述：

  1-(苯磺酰)-3-吲哚甲醛 、 3-奎宁环酮盐酸盐 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (Z)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  (Z)-2-(1-Phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one and (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol

  摘要：

  The title compounds, C22H20N2O3S, ( I), and C22H22N2O3S, (II), crystallize in space groups P(1) over bar and P2(1)2(1)2(1), respectively. The indole rings are planar and the benzene ring of the phenylsulfonyl group makes a dihedral angle with the mean plane of the indole ring of 90.2 (2)degrees in (I) and 94.0 (2)degrees in (II). In both molecules, the double bond connecting the azabicyclic and indole moieties has a Z geometry. Compound (II) was obtained as an enantiomerically pure crystal and has the 3S configuration.

  DOI：

  10.1107/s0108270104015847

文献信息

• (<i>Z</i>)-2-[(1-Phenylsulfonyl-1<i>H</i>-indol-3-yl)methylene]-1-azabicyclo[2.2.2]octan-3-one semicarbazone
  作者：Vijayakumar N. Sonar、M. Venkatraj、Sean Parkin、Peter A. Crooks

  DOI：10.1107/s0108270107006129

  日期：2007.5.15

  In crystals of the title compound, C23H23N5O3S, the indole system is planar and the phenyl ring of the phenylsulfonyl group makes a dihedral angle with the best plane of the indole system of 77.18 (4)degrees. The olefinic bond connecting the azabicyclic and indole systems has Z geometry. The geometry adopted by the C = O bond with respect to the N-N bond is trans. The O atom of the carbonyl group of each molecule is hydrogen bonded to the hydrazidic H atom of an adjacent molecule to form an eight-membered-ring dimeric structure.