(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline | 765253-06-3

• 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: (1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1R,3R)-2-benzyl-6-methoxy-1,3-dimethyl-8-propan-2-yloxy-3,4-dihydro-1H-isoquinoline
• CAS: 765253-06-3
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: ZJMWUXYBBNEULY-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 在 4-二甲氨基吡啶 、 sodium thioisopropylate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (1R,3R)-(N-benzyl-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-yl) 1'-bromo-5'-isopropoxy-4'-methoxy-2'-naphthoate
  参考文献：
  名称：

  First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C

  摘要：

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10301-5
• 作为产物：
  描述：

  (1R,3R)-2-Benzyl-6-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol 、 2-溴丙烷 在 sodium hydroxide 、 三丁基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以87%的产率得到(1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C

  摘要：

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10301-5

文献信息

• First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C
  作者：Gerhard Bringmann、Jörg Holenz、Ralf Weirich、Martin Rübenacker、Christian Funke、Michael R. Boyd、Robert J. Gulakowski、Guido François

  DOI：10.1016/s0040-4020(97)10301-5

  日期：1998.1

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.