N-[(3-methyl-2-butenyl)oxycarbonyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 648910-20-7

• 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: N-[(3-methyl-2-butenyl)oxycarbonyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 3-methylbut-2-enyl 6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 648910-20-7
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: LOZGVLYIHFPKAP-UHFFFAOYSA-N

物化性质

• 熔点：
  74-75 °C(Solv: ligroine (8032-32-4))
• 沸点：
  427.7±45.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(3-methyl-2-butenyl)oxycarbonyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 碘 、 锌 作用下， 以 甲醇 为溶剂， 反应 7.5h， 以78%的产率得到6,7-二甲氧基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc

  摘要：

  The prenyloxycarbonyl (Preoc) moiety was efficiently removed from carbamates to provide the corresponding amines in good to excellent yields (63-88%) by using iodine in methanol followed by treatment of the resulting beta-methoxyiodides by zinc powder. The reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic methyl ethers. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.058
• 作为产物：
  描述：

  异戊烯醇 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 N-[(3-methyl-2-butenyl)oxycarbonyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Prenyl carbamates: preparation and deprotection

  摘要：

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.028