1-Bromo-4-isopropoxy-5-methoxy-7-methylnaphthalene | 162147-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Bromo-4-isopropoxy-5-methoxy-7-methylnaphthalene
• 英文别名: 5-Bromo-8-isopropoxy-1-methoxy-3-methylnaphthalene；5-bromo-1-methoxy-3-methyl-8-propan-2-yloxynaphthalene
• CAS: 162147-14-0
• 化学式: C₁₅H₁₇BrO₂
• 分子量: 309.203
• InChiKey: XOPPNVODXSAHCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Bromo-4-isopropoxy-5-methoxy-7-methylnaphthalene 在 四(三苯基膦)钯 potassium phosphate 、 正丁基锂 、 三氯化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 83.79h， 生成 4-(6,8-Dimethoxy-trans-1,3-dimethylisochroman-5-yl)-8-methoxy-6-methyl-1-naphthol
  参考文献：
  名称：

  Syntheses of isochromane analogues of the michellamines and korupensamines

  摘要：

  本文介绍了氧类似物 6、7 和 8 的合成过程。外消旋 5-碘-6,8-二甲氧基-反式-1,3-二甲基异色胺 10 是由 2,4-二甲氧基苯甲醛经 11 个步骤合成的，总收率为 51%。异丙氧基类似物 11 的合成方法与此类似。用铃木法将异铬烷 10 与 4-异丙氧基-5-甲氧基-7-甲基萘-1-硼酸 9 结合，制得 7，收率为 96%。通过氧化二聚化，然后还原交叉共轭的烯二酮中间体 45，以良好的收率将其转化为所需的产品 6。

  DOI：

  10.1039/a908367g
• 作为产物：
  描述：

  3-(1-甲基乙氧基)-苯甲醛 在 lithium aluminium tetrahydride 、 1,2-二溴四氯乙烷 、 水 、 溴 、 sodium ethanolate 、 sodium acetate 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 46.5h， 生成 1-Bromo-4-isopropoxy-5-methoxy-7-methylnaphthalene
  参考文献：
  名称：

  First Total Synthesis of Korupensamines A and B

  摘要：

  The first total synthesis of korupensamines A (1a) and B (1b), highly polar naphthylisoquinoline alkaloids and, simultaneously, 'monomeric building blocks' of the michellamines, is described. Key step is the Pd-II catalyzed intermolecular biaryl coupling of the two appropriately protected naphthalene and isoquinoline moieties (10) and (11), with the coupling positions activated by bromine and trialkylstannane substituents respectively.

  DOI：

  10.3987/com-94-s(b)79

文献信息

• Syntheses of isochromane analogues of the michellamines and korupensamines
  作者：Charles B. de Koning、Joseph P. Michael、Willem A. L. van Otterlo

  DOI：10.1039/a908367g

  日期：——

  Syntheses of the oxygen analogues 6, 7 and 8 of the michellamines 1 and korupensamines 2 are described. Racemic 5-iodo-6,8-dimethoxy-trans-1,3-dimethylisochromane 10 was synthesised in eleven steps from 2,4-dimethoxybenzaldehyde in an overall yield of 51%. The isopropoxy analogue 11 was synthesised in a similar manner. Isochromane 10 was coupled using Suzuki methodology with 4-isopropoxy-5-methoxy-7-methylnaphthalene-1-boronic acid 9 to produce 7 in 96% yield. This was converted in good yield into the desired product 6 by oxidative dimerisation followed by reduction of the cross-conjugated ene-dione intermediate 45.

  本文介绍了氧类似物 6、7 和 8 的合成过程。外消旋 5-碘-6,8-二甲氧基-反式-1,3-二甲基异色胺 10 是由 2,4-二甲氧基苯甲醛经 11 个步骤合成的，总收率为 51%。异丙氧基类似物 11 的合成方法与此类似。用铃木法将异铬烷 10 与 4-异丙氧基-5-甲氧基-7-甲基萘-1-硼酸 9 结合，制得 7，收率为 96%。通过氧化二聚化，然后还原交叉共轭的烯二酮中间体 45，以良好的收率将其转化为所需的产品 6。
• Monomeric Naphthylisoquinoline alkaloids and synthesis methods thereof
  申请人：The United States of America, as represented by the Department of Health

  公开号：US05552550A1

  公开（公告）日：1996-09-03

  The present invention provides methods of preparing monomeric naphthylisoquinoline alkaloids, including the antiparasitic korupensamines and related compounds, as well as non-korupensamines and other monomeric naphthylisoquinoline alkaloids. The invention also provides new, medically useful naphthylisoquinoline compounds and derivatives thereof.

  本发明提供了制备单体萘异喹啉生物碱的方法，包括抗寄生虫的科鲁彭萘异喹啉生物碱和相关化合物，以及非科鲁彭萘异喹啉生物碱和其他单体萘异喹啉生物碱。本发明还提供了新的、具有医学用途的萘异喹啉化合物及其衍生物。
• Monomeric naphthylisoquinoline alkaloids and synthesis methods thereof
  申请人：The United States of America as represented by the Secretary, Department

  公开号：US05763613A1

  公开（公告）日：1998-06-09

  The present invention provides methods of preparing monomeric naphthylisoquinoline alkaloids, including the antiparasitic korupensamines and related compounds, as well as non-korupensamines and other monomeric naphthylisoquinoline alkaloids. The invention also provides new, medically useful naphthylisoquinoline compounds and derivatives thereof.

  本发明提供了制备单体萘异喹啉生物碱的方法，包括抗寄生虫的科鲁彭萘异喹啉生物碱及相关化合物，以及非科鲁彭萘异喹啉生物碱和其他单体萘异喹啉生物碱。本发明还提供了新的、具有医学用途的萘异喹啉化合物及其衍生物。
• Unprecedented Direct Asymmetric Total Syntheses of 5,8’‐Naphthylisoquinoline Alkaloids from their Fully Substituted Precursors Employing a Novel Nickel/N,N‐ligand‐Catalyzed Atroposelective Cross‐Coupling Reaction
  作者：Dino Berthold、Willem A. L. van Otterlo

  DOI：10.1002/chem.202302070

  日期：2023.11.2

  Four different 5,8’-coupled naphthylisoquinoline alkaloids have been prepared via a general and concise synthetic pathway directly from the corresponding cross-coupling reaction precursors. For the cross-coupling key step, a new Negishi cross-coupling reaction, employing a Ni/N,N-ligand-based catalyst providing the natural products in good yields and high enantiomeric purities, has been developed.

  四种不同的 5,8'-偶联萘基异喹啉生物碱已通过通用且简洁的合成途径直接从相应的交叉偶联反应前体制备。对于交叉偶联的关键步骤，开发了一种新的根岸交叉偶联反应，采用基于 Ni/N,N-配体的催化剂，以良好的收率和高对映体纯度提供天然产物。此外，我们还报告了一种在萘基异喹啉天然产物中发现的北部 1,8-二氧基萘结构单元的新方法，利用 Hartwig 的硼化/甲基化策略，可以有效安装正交保护基团。
• Monomeric and dimeric naphtylisoquinoline alkaloids and synthesis methods thereof
  申请人：THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, Department of Health and Human Services

  公开号：EP1325915A1

  公开（公告）日：2003-07-09

  The present invention provides methods of preparing monomeric naphthylisoquinoline alkaloids, including the antiparasitic korupensamines and related compounds, as well as non-korupensamines and other monomeric naphthylisoquinoline alkaloids. The present invention also provides methods of preparing dimeric naphthylisoquinoline alkaloids by coupling together two monomeric naphthylisoquinoline alkaloids, each of which may be the same or different, and one, both, or neither of which may possess a C-8' to C-5 naphthalene/isoquinoline linkage, to form homodimers or heterodimers, including the antiviral michellamines. The present invention further provides new, medically useful monomeric naphthylisoquinoline compounds and homodimeric and heterodimeric naphthylisoquinoline compounds and derivatives thereof.

  本发明提供了制备单体萘基异喹啉生物碱的方法，包括抗寄生虫的korupensamines和相关化合物，以及非korupensamines和其他单体萘基异喹啉生物碱。本发明还提供了通过将两种单体萘基异喹啉生物碱偶联在一起制备二聚体萘基异喹啉生物碱的方法，每种单体萘基异喹啉生物碱可以是相同的或不同的，其中一种、两种或两种都不具有 C-8' 至 C-5 萘/异喹啉连接，形成同二聚体或异二聚体，包括抗病毒的小檗胺。本发明进一步提供了新的、在医学上有用的单体萘异喹啉化合物和同源二聚体和异源二聚体萘异喹啉化合物及其衍生物。