1,4-Naphthalenedione, 2-hydroxy-7-(4-methylpentyl)- | 500217-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Naphthalenedione, 2-hydroxy-7-(4-methylpentyl)-
• 英文别名: 2-hydroxy-7-(4-methylpentyl)-1,4-naphthoquinone
• CAS: 500217-64-1
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: ZJJDMVYVFMSZQL-UHFFFAOYSA-N

物化性质

• 沸点：
  419.7±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,4-Naphthalenedione, 2-hydroxy-7-(4-methylpentyl)- 在 硫酸 作用下， 反应 1.0h， 以150 mg的产率得到2-acetoxy-7-(4-methylpentyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones

  摘要：

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.

  DOI：

  10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m
• 作为产物：
  描述：

  6-(2-(3,3-dimethylpropoxycarbonyl-2-yl)ethyl)naphthalene-1,4-dione 在 Lindlar's catalyst 氢氧化钾 、 氢气 、 溴 、 碳酸氢钠 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 28.5h， 生成 1,4-Naphthalenedione, 2-hydroxy-7-(4-methylpentyl)-
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones

  摘要：

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.

  DOI：

  10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m

文献信息

• New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones
  作者：José M. Miguel del Corral、M. Angeles Castro、Alaide B. Oliveira、Simone A. Gualberto、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1016/j.bmc.2006.06.053

  日期：2006.11

  A series of new furoterpenyl-1,4-naphtho(anthra)quinones have been prepared via oxidative cyclization of the corresponding 2-hydroxy-3-butenyl-1,4-naphtho(anthra)quinones. Depending on the reaction conditions the 1,2-quinones or the 1,4-quinones were obtained. Several new furo-1,4-anthraquinones were also obtained by condensation of 2,3-dichloroquinones with 1,3-dicarbonyls. The compounds synthesized have been evaluated for their cytotoxicity against neoplastic cell lines, some of them being effective below the micromolar level. (c) 2006 Elsevier Ltd. All rights reserved.