4-羟基-7,8-二甲氧基-5-(苯基甲氧基)-2-萘羧酸乙酯 | 828940-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-羟基-7,8-二甲氧基-5-(苯基甲氧基)-2-萘羧酸乙酯
• 英文名称: 5-Benzyloxy-4-hydroxy-7,8-dimethoxy-naphthalene-2-carboxylic acid ethyl ester
• 英文别名: 2-Naphthalenecarboxylic acid, 4-hydroxy-7,8-dimethoxy-5-(phenylmethoxy)-, ethyl ester；ethyl 4-hydroxy-7,8-dimethoxy-5-phenylmethoxynaphthalene-2-carboxylate
• CAS: 828940-38-1
• 化学式: C₂₂H₂₂O₆
• 分子量: 382.413
• InChiKey: FQBYVFPAPIUZOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-羟基-7,8-二甲氧基-5-(苯基甲氧基)-2-萘羧酸乙酯 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 pyridinium hydrobromide perbromide 、 pyridine-SO3 complex 、 四丁基氟化铵 、 水 、 三溴化硼 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 56.5h， 生成 Acetic acid (E)-4-[4-hydroxy-3-(1-hydroxy-pentyl)-7-methylamino-5,8-dioxo-5,8-dihydro-naphthalen-2-yl]-but-2-enyl ester
  参考文献：
  名称：

  The Synthesis and Biological Activity of Pyranonaphthoquione Derivatives fromStreptomycessp. and Their Related Substances

  摘要：

  具有Cdc25A磷酸酶抑制活性的新型吡喃并萘醌（2）的合成得以实现。该合成途径的关键步骤是分子内迈克尔加成反应，用于构建吡喃环系统。对从2的合成中间体中容易获得的几种衍生物的抑制活性进行了评估。结果数据表明，吡喃环部分不是活性关键因素。

  DOI：

  10.1246/bcsj.77.1925
• 作为产物：
  描述：

  5-(benzyloxy)-2,3-dimethoxybenzaldehyde 在 potassium acetate 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 4-羟基-7,8-二甲氧基-5-(苯基甲氧基)-2-萘羧酸乙酯
  参考文献：
  名称：

  Synthesis of (±)-pyranonaphthoquinone derivatives, a Cdc25A phosphatase inhibitor

  摘要：

  The novel pyranonaphthoquinone 2, carrying Cdc25A phosphatase inhibitory activity, has been successfully synthesized through tricyclic compound 16, which was obtained from 15 by using the intramolecular Michael addition. The precursor 9 was derived from 5-bromoveratraldehyde. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.120

文献信息

• Synthesis of the naphthalene-derived inhibitors against Cdc25A dual-specificity protein phosphatase and their biological activity
  作者：Akiko Shimbashi、Ayako Tsuchiya、Masaya Imoto、Shigeru Nishiyama

  DOI：10.1016/j.bmcl.2004.10.034

  日期：2005.1

  The novel naphthalene-type analogues 14 and 18 and the naphthoquinone-type analogues, 8, 9, 15, 16, 19, 21, 22, and 2328 have been synthesized, and their in vitro Cdc25A phosphatase-inhibitory activity was examined. In assessment of the inhibitory activity, it was revealed that the naphthoquinone core is contributed to the activity, rather than the alkyl side chain. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of (±)-pyranonaphthoquinone derivatives, a Cdc25A phosphatase inhibitor
  作者：Akiko Shimbashi、Yuichi Ishikawa、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2003.11.120

  日期：2004.1

  The novel pyranonaphthoquinone 2, carrying Cdc25A phosphatase inhibitory activity, has been successfully synthesized through tricyclic compound 16, which was obtained from 15 by using the intramolecular Michael addition. The precursor 9 was derived from 5-bromoveratraldehyde. (C) 2003 Elsevier Ltd. All rights reserved.
• The Synthesis and Biological Activity of Pyranonaphthoquione Derivatives from<i>Streptomyces</i>sp. and Their Related Substances
  作者：Akiko Shimbashi、Ayako Tsuchiya、Masaya Imoto、Shigeru Nishiyama

  DOI：10.1246/bcsj.77.1925

  日期：2004.10

  The total synthesis of a novel pyranonaphthoquinone (2) having Cdc25A phosphatase inhibitory activity is achieved. The key step in this synthetic pathway is the intramolecular Michael addition for construction of the pyran ring system. The inhibitory activity of several derivatives, readily obtained from synthetic intermediates of 2, is assessed. The resulting data indicates that the pyran ring moiety is not a crucial factor for the activity.

  具有Cdc25A磷酸酶抑制活性的新型吡喃并萘醌（2）的合成得以实现。该合成途径的关键步骤是分子内迈克尔加成反应，用于构建吡喃环系统。对从2的合成中间体中容易获得的几种衍生物的抑制活性进行了评估。结果数据表明，吡喃环部分不是活性关键因素。