3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 1363394-60-8

• 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: 3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 1363394-60-8
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: GUVWTRINPPFWAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6-(4-isopropoxyphenethyl)-2,3-dimethoxybenzaldehyde 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 C₃₂H₁₉N₂O₈P 、 正丁基锂 、 双氧水 、 三氯化硼 、 sodium hydride 、 sodium hydroxide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.58h， 生成 3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine

  摘要：

  An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (+/-)-tetrahydropalmatine was achieved by exploiting this new transformation.

  DOI：

  10.1021/ol300180w

文献信息

• Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine
  作者：Keiji Mori、Taro Kawasaki、Takahiko Akiyama

  DOI：10.1021/ol300180w

  日期：2012.3.16

  An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (+/-)-tetrahydropalmatine was achieved by exploiting this new transformation.