(8RS)-7,8-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine | 1336919-42-6

• 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: (8RS)-7,8-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine
• 英文别名: 11,12-dimethyl-11,21-diazatetracyclo[12.7.0.03,8.015,20]henicosa-1(14),3,5,7,15,17,19-heptaene
• CAS: 1336919-42-6
• 化学式: C₂₁H₂₄N₂
• 分子量: 304.435
• InChiKey: WQPRXYGVHKQNOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (8RS)-7,8-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine 在 Chiracel OD column 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 (8S)-7,8-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine 、 (8R)-7,8-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine
  参考文献：
  名称：

  Chiral Indolo[3,2-f][3]benzazecine-Type Dopamine Receptor Antagonists: Synthesis and Activity of Racemic and Enantiopure Derivatives

  摘要：

  Racemic and enantiopure 8-substituted derivatives of the lead dopamine receptor antagonist LE 300 (1) were prepared, and their affinities for the dopamine receptors (D(1)-D(5)) were tested. The separate enantiomers showed significantly different affinities; the (8S)-methyl and (8R)-hyroxymethyl derivatives where the substituents point below the reference plane of the indolo[3,2-f][3]benzazecine scaffold were markedly more active than their enantiomeric counterparts. The racemic 8-carboxy derivative was shown to be selective for the D(5)-receptor, even against D(1).

  DOI：

  10.1021/jm200676f
• 作为产物：
  描述：

  3-(2-nitroprop-1-en-1-yl)-1H-indole 在 lithium aluminium tetrahydride 、 氨 、 sodium 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 反应 36.17h， 生成 (8RS)-7,8-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f][3]benzazecine
  参考文献：
  名称：

  Chiral Indolo[3,2-f][3]benzazecine-Type Dopamine Receptor Antagonists: Synthesis and Activity of Racemic and Enantiopure Derivatives

  摘要：

  Racemic and enantiopure 8-substituted derivatives of the lead dopamine receptor antagonist LE 300 (1) were prepared, and their affinities for the dopamine receptors (D(1)-D(5)) were tested. The separate enantiomers showed significantly different affinities; the (8S)-methyl and (8R)-hyroxymethyl derivatives where the substituents point below the reference plane of the indolo[3,2-f][3]benzazecine scaffold were markedly more active than their enantiomeric counterparts. The racemic 8-carboxy derivative was shown to be selective for the D(5)-receptor, even against D(1).

  DOI：

  10.1021/jm200676f