(+/-)-3,3a,4,5-tetrahydro-6-methoxy-3-methyl-2H-benz[e]indol-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-3,3a,4,5-tetrahydro-6-methoxy-3-methyl-2H-benz[e]indol-2-one
• 英文别名: 6-methoxy-3-methyl-4,5-dihydro-3aH-benzo[e]indol-2-one
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: CTNIMMAFNSIICK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 四氢吡咯 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 (+/-)-3,3a,4,5-tetrahydro-6-methoxy-3-methyl-2H-benz[e]indol-2-one
  参考文献：
  名称：

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles: synthesis and evaluation of dopamine D2 and D3 receptor binding affinity

  摘要：

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles were synthesized as conformationally rigid analogues of 3-phenylpyrrolidine and evaluated for dopamine (DA) D-2S and D-3 receptor binding affinity. The tricyclic benz[e]indole nucleus was constructed by a previously reported reductive amination-cyclization procedure. Several unexpected side products were isolated and characterized using the general method. The trans-diastereoisomers exhibited greater affinities for the DA D-3 receptor than the corresponding cis-isomers. In both the cis- and trans- series the greatest affinity for DA D-3 receptors was shown by compounds substituted with N-n propyl or N-allyl groups. The cis-(+/-)-N-allyl derivative 21e demonstrated a D-2S /D-3 selectivity of 290. Resolution of cis-(+/-)-5 and trans-(+/-)-21c into individual enantiomers showed that in both series the more active isomer had 3aR absolute configuration. These novel Ligands may be useful tools for gaining additional information about the DA D-3 receptor. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80098-1

文献信息

• cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles: synthesis and evaluation of dopamine D2 and D3 receptor binding affinity
  作者：Xiaodong Song、A.Michael Crider、Sharon F. Cruse、Debasis Ghosh、Cheryl Klein-Stevens、Li Liang、Mark A. Scheideler、Annemarie Varming、Inger Søtofte

  DOI：10.1016/s0223-5234(99)80098-1

  日期：1999.6

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles were synthesized as conformationally rigid analogues of 3-phenylpyrrolidine and evaluated for dopamine (DA) D-2S and D-3 receptor binding affinity. The tricyclic benz[e]indole nucleus was constructed by a previously reported reductive amination-cyclization procedure. Several unexpected side products were isolated and characterized using the general method. The trans-diastereoisomers exhibited greater affinities for the DA D-3 receptor than the corresponding cis-isomers. In both the cis- and trans- series the greatest affinity for DA D-3 receptors was shown by compounds substituted with N-n propyl or N-allyl groups. The cis-(+/-)-N-allyl derivative 21e demonstrated a D-2S /D-3 selectivity of 290. Resolution of cis-(+/-)-5 and trans-(+/-)-21c into individual enantiomers showed that in both series the more active isomer had 3aR absolute configuration. These novel Ligands may be useful tools for gaining additional information about the DA D-3 receptor. (C) Elsevier, Paris.