(6aR,9S)-7-methyl-4-tosyl-9-vinyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline | 1228274-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (6aR,9S)-7-methyl-4-tosyl-9-vinyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline
• 英文别名: (6aR,9S)-9-ethenyl-7-methyl-4-(4-methylphenyl)sulfonyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline
• CAS: 1228274-09-6
• 化学式: C₂₄H₂₄N₂O₂S
• 分子量: 404.533
• InChiKey: HDGOCZWQVZENLI-GAJHUEQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6aR,9S)-7-methyl-4-tosyl-9-vinyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline 在 四氧化锇 、 四甲基乙二胺 、 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 以72%的产率得到1-((6aR,9S)-7-methyl-4-tosyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)ethane-1,2-diol
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis

  摘要：

  The first enantioselective synthesis of (+)-isolysergol was completed in 12 steps from commercially available materials by a novel approach that features a late stage microwave-mediated, diastereomeric ring-closing metathesis catalyzed by a chiral molybdenum catalyst to simultaneously form the D ring and set the stereocenter at C(8).

  DOI：

  10.1021/ol100819f
• 作为产物：
  描述：

  (R)-2,6,7,8-tetrahydro-N-methyl-6-methylene-2-tosyl-N-(2-vinylbut-3-enyl)benzo[cd]indol-7-amine 在 Schrock catalyst 作用下， 以 苯 为溶剂， 反应 0.5h， 以54%的产率得到(6aR,9S)-7-methyl-4-tosyl-9-vinyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis

  摘要：

  The first enantioselective synthesis of (+)-isolysergol was completed in 12 steps from commercially available materials by a novel approach that features a late stage microwave-mediated, diastereomeric ring-closing metathesis catalyzed by a chiral molybdenum catalyst to simultaneously form the D ring and set the stereocenter at C(8).

  DOI：

  10.1021/ol100819f

文献信息

• Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis
  作者：Jason A. Deck、Stephen F. Martin

  DOI：10.1021/ol100819f

  日期：2010.6.4

  The first enantioselective synthesis of (+)-isolysergol was completed in 12 steps from commercially available materials by a novel approach that features a late stage microwave-mediated, diastereomeric ring-closing metathesis catalyzed by a chiral molybdenum catalyst to simultaneously form the D ring and set the stereocenter at C(8).