1-(4-(benzyloxy)benzyl)-6,7-dimethoxyisoquinoline 2-oxide | 1151986-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(4-(benzyloxy)benzyl)-6,7-dimethoxyisoquinoline 2-oxide
• CAS: 1151986-09-2
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: QBXOSBUXHYIFPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  54.63
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-(benzyloxy)benzyl)-6,7-dimethoxyisoquinoline 2-oxide 在 10% palladium on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 24.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以87%的产率得到crykonisine
  参考文献：
  名称：

  Catalyst and base controlled site-selective sp2 and sp3 direct arylation of azine N-oxides

  摘要：

  Site-selective direct arylation of both sp(2) and sp(3) sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner The sp arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and. rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement of the base in the mechanism of these reactions. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.12.004
• 作为产物：
  描述：

  4-苄氧基溴苯 、 6,7-二甲氧基-1-甲基异喹啉 2-氧化物 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以55%的产率得到1-(4-(benzyloxy)benzyl)-6,7-dimethoxyisoquinoline 2-oxide
  参考文献：
  名称：

  Catalyst and base controlled site-selective sp2 and sp3 direct arylation of azine N-oxides

  摘要：

  Site-selective direct arylation of both sp(2) and sp(3) sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner The sp arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and. rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement of the base in the mechanism of these reactions. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.12.004