8-溴-4-羟基-5-(1-甲基乙氧基)-2-萘羧酸乙酯 | 162147-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 8-溴-4-羟基-5-(1-甲基乙氧基)-2-萘羧酸乙酯
• 英文名称: Ethyl 8-bromo-4-hydroxy-5-isopropoxy-2-naphthoate
• 英文别名: 2-Naphthalenecarboxylic acid, 8-bromo-4-hydroxy-5-(1-methylethoxy)-, ethyl ester；ethyl 8-bromo-4-hydroxy-5-propan-2-yloxynaphthalene-2-carboxylate
• CAS: 162147-17-3
• 化学式: C₁₆H₁₇BrO₄
• 分子量: 353.213
• InChiKey: LLQBMOCNAQNASG-UHFFFAOYSA-N

物化性质

• 沸点：
  492.4±40.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  8-溴-4-羟基-5-(1-甲基乙氧基)-2-萘羧酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 1,2-二溴四氯乙烷 、 三丁基氯化锡 、 叔丁基锂 、 potassium carbonate 、 三苯基膦 、 lithium chloride 、 copper(I) bromide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 60.5h， 生成 N-Benzyl-6,8-di-O-benzyl-5'-O-isopropylkorupensamine A/B
  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
• 作为产物：
  描述：

  3-(1-甲基乙氧基)-苯甲醛 在 水 、 溴 、 sodium ethanolate 、 sodium acetate 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 8-溴-4-羟基-5-(1-甲基乙氧基)-2-萘羧酸乙酯
  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

• 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。
• 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。
• MONOMERIC AND DIMERIC NAPHTHYLISOQUINOLINE ALKALOIDS AND SYNTHESIS METHODS THEREOF
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary of the Department of Health and Human Services

  公开号：EP0772595A1

  公开（公告）日：1997-05-14
• US5552550A
  申请人：——

  公开号：US5552550A

  公开（公告）日：1996-09-03