(+)-(S)-6,8-bis-(4-methoxybenzyloxy)-1-ethenyl-2-trifluoroacetyl-3,4-dihydro-1H-isoquinoline | 1314093-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (+)-(S)-6,8-bis-(4-methoxybenzyloxy)-1-ethenyl-2-trifluoroacetyl-3,4-dihydro-1H-isoquinoline
• 英文别名: 1-[(1S)-1-ethenyl-6,8-bis[(4-methoxyphenyl)methoxy]-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoroethanone
• CAS: 1314093-80-5
• 化学式: C₂₉H₂₈F₃NO₅
• 分子量: 527.54
• InChiKey: JGPPJYARKOSKOG-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+)-(S)-6,8-bis-(4-methoxybenzyloxy)-1-ethenyl-2-trifluoroacetyl-3,4-dihydro-1H-isoquinoline 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以98%的产率得到(+)-(S)-6,8-bis(4-methoxybenzyloxy)-3,4-dihydro-1-ethenyl-1H-isoquinoline
  参考文献：
  名称：

  Formal Enantioselective Total Synthesis of Schulzeines A–C via Pd–Catalyzed Intramolecular Asymmetric Allylic Amination

  摘要：

  Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.

  DOI：

  10.1021/jo2009615
• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 四甲基乙二胺 、 C₆₂H₆₄O₂P₂ 、 ammonium acetate 、 氢气 、 nickel diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 96.83h， 生成 (+)-(S)-6,8-bis-(4-methoxybenzyloxy)-1-ethenyl-2-trifluoroacetyl-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  Formal Enantioselective Total Synthesis of Schulzeines A–C via Pd–Catalyzed Intramolecular Asymmetric Allylic Amination

  摘要：

  Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.

  DOI：

  10.1021/jo2009615

文献信息

• Formal Enantioselective Total Synthesis of Schulzeines A–C via Pd–Catalyzed Intramolecular Asymmetric Allylic Amination
  作者：Chi-Feng Lin、Iwao Ojima

  DOI：10.1021/jo2009615

  日期：2011.8.5

  Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.