2-butyl-4-methoxynaphthalen-1-ol | 99107-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-butyl-4-methoxynaphthalen-1-ol
• 英文别名: 2-n-butyl-4-methoxynaphthol；1-Naphthalenol, 2-butyl-4-methoxy-
• CAS: 99107-70-7
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: AXXSITVSEZLWHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-butyl-4-methoxynaphthalen-1-ol 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以92%的产率得到2-butyl-1,4-naphthoquinone
  参考文献：
  名称：

  1,4-Dihydronaphthoquinones, hydroindoloquinones, benzofurans, and benzothiophenes as inhibitors of 5-lipoxygenase. Synthesis and structure-activity studies

  摘要：

  A series of substituted 1,4-dihydronaphthoquinones, hydroindoloquinones, benzofuran-4,7-dihydroquinones, and benzothiophene-4,7-dihydroquinones were synthesized and evaluated for inhibitory activity against 5-lipoxygenase. These compounds were found to be active in vitro for LTC4/D4 inhibition with the potencies (IC50's) ranging from 0.2 to 85 microM. Active 1,4-dihydronaphthoquinone acetates (IC50 less than 20 microM) were evaluated in an ex vivo LTB4 inhibition assay. The acetates of 1,4-dihydronaphthoquinones containing the alkyl substituent(s) (2-n-butyl, 11, and 2,3-diethyl, 15) exhibited the best activity in LTC4/D4 inhibition (IC50 = 0.2-0.4 microM, in vitro) as well as in LTB4 inhibition (60-75% inhibition).

  DOI：

  10.1021/jm00164a050
• 作为产物：
  描述：

  2-butyl-3-trimethylsilyl-4-methoxynaphthalen-1-ol 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 以46%的产率得到2-butyl-4-methoxynaphthalen-1-ol
  参考文献：
  名称：

  费歇尔卡宾配合物与三烷基甲硅烷基取代的炔烃的热和光化学反应

  摘要：

  Fischer卡宾配合物与三异丙基甲硅烷基（TIPS）取代的炔烃在苯中的热反应提供了以TIPS取代的乙烯基烯酮或2-TIPS取代的环丁烯酮为主要产品，而Fischer卡宾配合物与三甲基甲硅烷基（TMS）取代的炔烃在乙腈中的光化学反应提供了3-TMS取代的环丁烯酮。

  DOI：

  10.1016/j.jorganchem.2007.11.007

文献信息

• A novel and highly regioselective Cr-mediated route to functionalised quinone boronic ester derivatives
  作者：Mark W. Davies、Joseph P. A. Harrity、Christopher N. Johnson

  DOI：10.1039/a906643h

  日期：——

  A novel and highly regioselective route to quinone boronic ester derivatives has been developed using a Fischer carbene mediated benzannulation process.

  利用费舍尔碳烯介导的苯并环化工艺，开发出了一种新型的高区域选择性醌硼酸酯衍生物制备方法。
• Substituted naphthalenes, indoles, benzofurans and benzothiophenes as lipoxygenase inhibitors
  申请人：THE UPJOHN COMPANY

  公开号：EP0146348B1

  公开（公告）日：1991-07-31
• YAMASHITA, A.;TIMKO, J. M.;WATT, W., TETRAHEDRON LETT., 29,(1988) N 21, C. 2513-2516
  作者：YAMASHITA, A.、TIMKO, J. M.、WATT, W.

  DOI：——

  日期：——
• US4737519A
  申请人：——

  公开号：US4737519A

  公开（公告）日：1988-04-12
• 1,4-Dihydronaphthoquinones, hydroindoloquinones, benzofurans, and benzothiophenes as inhibitors of 5-lipoxygenase. Synthesis and structure-activity studies
  作者：Ayako Yamashita、Robert G. Schaub、Michael K. Bach、Gordon J. White、Arthur Toy、Nabil B. Ghazal、Michael D. Burdick、John R. Brashler、Marilyn S. Holm

  DOI：10.1021/jm00164a050

  日期：1990.2

  A series of substituted 1,4-dihydronaphthoquinones, hydroindoloquinones, benzofuran-4,7-dihydroquinones, and benzothiophene-4,7-dihydroquinones were synthesized and evaluated for inhibitory activity against 5-lipoxygenase. These compounds were found to be active in vitro for LTC4/D4 inhibition with the potencies (IC50's) ranging from 0.2 to 85 microM. Active 1,4-dihydronaphthoquinone acetates (IC50 less than 20 microM) were evaluated in an ex vivo LTB4 inhibition assay. The acetates of 1,4-dihydronaphthoquinones containing the alkyl substituent(s) (2-n-butyl, 11, and 2,3-diethyl, 15) exhibited the best activity in LTC4/D4 inhibition (IC50 = 0.2-0.4 microM, in vitro) as well as in LTB4 inhibition (60-75% inhibition).