N-formyl-1,2,3,4-tetrahydro-6-methoxy-1-(3,4-dimethoxy-benzyl)-7-phenylmethoxyisoquinoline | 263360-59-4

• 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: N-formyl-1,2,3,4-tetrahydro-6-methoxy-1-(3,4-dimethoxy-benzyl)-7-phenylmethoxyisoquinoline
• 英文别名: 1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
• CAS: 263360-59-4
• 化学式: C₂₇H₂₉NO₅
• 分子量: 447.531
• InChiKey: KZRYJQMTDOJGDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-formyl-1,2,3,4-tetrahydro-6-methoxy-1-(3,4-dimethoxy-benzyl)-7-phenylmethoxyisoquinoline 在 甲烷 、 palladium dichloride 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.5h， 生成 6-acetoxy-N-formyl-1,2,3,4,6,7-hexahydro-6-methoxy-1-(3,4-dimethoxy-benzyl)-7-oxoisoquinoline
  参考文献：
  名称：

  Formation and Reaction of o-Quinol Acetates of N-Acyl- and N-Methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols

  摘要：

  Oxidation of N-formyl-, N-acetyl-, N-ethoxycarbonyl-, and N-methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols (1b-e) with lead tetraacetate in dichloromethane (CH2Cl2) produced quantitatively corresponding o-quinol acetates (2b-e), treatment of which with trifluoroacetic acid in CH2Cl2 at 0 degrees C for a few minutes afforded corresponding N-acyl- and N-methanesulfonyl-wilsonirines (4b-e) and N-acyl- and N-methanesulfonylnorsebiferines (5b-e). When the reaction was carried out at room temperature, o-quinol acetates (2d,e) of N-ethoxycarbonyl and N-methanesulfonyl congeners (Id,e) gave 1-[2(ethoxycarbonylamino)ethyl]- and 1-[2-(methanesulfonylamino)ethyl]-4-hydroxy-3,6,7-trimethoxyphenanthrenes (8d,e).

  DOI：

  10.3987/com-99-s84
• 作为产物：
  描述：

  (+/-)-7-benzyloxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 、 甲酸乙酯 反应 2.0h， 以98%的产率得到N-formyl-1,2,3,4-tetrahydro-6-methoxy-1-(3,4-dimethoxy-benzyl)-7-phenylmethoxyisoquinoline
  参考文献：
  名称：

  Formation and Reaction of o-Quinol Acetates of N-Acyl- and N-Methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols

  摘要：

  Oxidation of N-formyl-, N-acetyl-, N-ethoxycarbonyl-, and N-methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols (1b-e) with lead tetraacetate in dichloromethane (CH2Cl2) produced quantitatively corresponding o-quinol acetates (2b-e), treatment of which with trifluoroacetic acid in CH2Cl2 at 0 degrees C for a few minutes afforded corresponding N-acyl- and N-methanesulfonyl-wilsonirines (4b-e) and N-acyl- and N-methanesulfonylnorsebiferines (5b-e). When the reaction was carried out at room temperature, o-quinol acetates (2d,e) of N-ethoxycarbonyl and N-methanesulfonyl congeners (Id,e) gave 1-[2(ethoxycarbonylamino)ethyl]- and 1-[2-(methanesulfonylamino)ethyl]-4-hydroxy-3,6,7-trimethoxyphenanthrenes (8d,e).

  DOI：

  10.3987/com-99-s84