5-Benzyloxy-1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline | 919082-27-2

• 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: 5-Benzyloxy-1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline
• 英文别名: 1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-5-phenylmethoxy-3,4-dihydroisoquinoline
• CAS: 919082-27-2
• 化学式: C₂₇H₂₉NO₅
• 分子量: 447.531
• InChiKey: HEQJBIUZQDFMQM-UHFFFAOYSA-N

物化性质

• 沸点：
  599.7±50.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Benzyloxy-1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、517.11 kPa 条件下， 反应 18.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 在 sodium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-Benzyloxy-1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h