1-bromo-5-isopropoxy-4-methoxy-2-naphthoic acid | 202215-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-5-isopropoxy-4-methoxy-2-naphthoic acid
• 英文别名: 2-Naphthalenecarboxylic acid, 1-bromo-5-isopropoxy-4-methoxy-；1-bromo-4-methoxy-5-propan-2-yloxynaphthalene-2-carboxylic acid
• CAS: 202215-69-8
• 化学式: C₁₅H₁₅BrO₄
• 分子量: 339.186
• InChiKey: JCPGCILDKKLEGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-bromo-5-isopropoxy-4-methoxy-2-naphthoic acid 在 bis-triphenylphosphine-palladium(II) chloride 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 甲酸 、 草酰氯 、 三正丁胺 、 1,2-二溴四氯乙烷 、 1,3-双(二苯基膦)丙烷 、 sodium acetate 、 thallium (I) ethoxide 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-benzyl-8,5'-di-O-isopropyldioncophylline C
  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 manganese(IV) oxide 、 sodium chlorite 、 lithium aluminium tetrahydride 、 氨基磺酸 、 氢气 、 sodium acetate 、 tetra-N-butylammonium tribromide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 20.0 ℃ 、500.0 kPa 条件下， 反应 23.0h， 生成 1-bromo-5-isopropoxy-4-methoxy-2-naphthoic acid
  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

• Directed joint total synthesis of the three naphthylisoquinoline alkaloids dioncolactone A, dioncopeltine A, and 5′-O-demethyldioncophylline A
  作者：Gerhard Bringmann、Wael Saeb、Martin Rübenacker

  DOI：10.1016/s0040-4020(98)01040-0

  日期：1999.1

  described. The regio- and stereo-selective construction of the biaryl axes was achieved through the ‘lactone methodology’, by ester-type prefixation of the two molecular moieties, intramolecular coupling, and atropo-diastereoselective cleavage of the lactone auxiliary bridge. As a novel alternative, the configuration at the axis may be installed by atroposelective hydroxy aldehyde reduction through dynamic

  的第一全合成三个抗疟疾naphthylisoquinoline生物碱dioncolactone A（4），dioncopeltine A（5），和5'- Ô -demethyldioncophylline A（6）进行说明。通过“内酯法”，通过两个分子部分的酯型前缀，分子内偶联和内酯辅助桥的对苯二酸-非对映选择性裂解，实现了芳基轴的区域和立体选择性构建。作为一种新颖的替代方案，可以通过动态动力学拆分通过对映选择性羟基醛还原来安装在轴上的构型。
• 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.