1-bromo-2-hydroxymethyl-5-isopropoxy-4-methoxynaphthalene | 202215-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-2-hydroxymethyl-5-isopropoxy-4-methoxynaphthalene
• 英文别名: (1-Bromo-4-methoxy-5-propan-2-yloxynaphthalen-2-yl)methanol
• CAS: 202215-66-5
• 化学式: C₁₅H₁₇BrO₃
• 分子量: 325.202
• InChiKey: XVSKKCONRPUDFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-2-hydroxymethyl-5-isopropoxy-4-methoxynaphthalene 在 bis-triphenylphosphine-palladium(II) chloride 4-二甲氨基吡啶 、 manganese(IV) oxide 、 sodium chlorite 、 草酰氯 、 氨基磺酸 、 sodium acetate 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 (1R,3R,4bM,4bP)-[1,2-d]-8-isopropoxy-9-methoxy-naphtho-[5,6-b]-N-benzyl-14-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolino-11H-pyran-11-one
  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：

  8-溴-4-甲氧基-5-(1-甲基乙氧基)-2-萘羧酸乙酯 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 sodium acetate 、 tetra-N-butylammonium tribromide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 1-bromo-2-hydroxymethyl-5-isopropoxy-4-methoxynaphthalene
  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.