1,4-Naphthalenedione, 5,8-dihydro-6-(4-methyl-3-pentenyl)- | 177327-04-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,4-Naphthalenedione, 5,8-dihydro-6-(4-methyl-3-pentenyl)-
• 英文别名: 6-(4-methylpent-3-enyl)-5,8-dihydronaphthalene-1,4-dione
• CAS: 177327-04-7
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: ZSZWLHLIALYGGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  367.0±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-Naphthalenedione, 5,8-dihydro-6-(4-methyl-3-pentenyl)- 在 Lindlar's catalyst manganese(IV) oxide 、 氢氧化钾 、 氢气 、 溴 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 乙醇 、 溶剂黄146 、 乙酸乙酯 、 苯 为溶剂， 反应 102.5h， 生成 2-Methoxy-7-(4-methyl-pentyl)-[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：

  月桂烯 、 对苯醌 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以67%的产率得到1,4-萘二醇,5,8-二氢-6-(4-甲基-3-戊烯基)-
  参考文献：
  名称：

  Further antineoplastic terpenylquinones and terpenylhydroquinones

  摘要：

  Influences of the quinone/hydroquinone fragment and other structural features are considered in relation with the antineoplastic activity and selectivity of terpenylquinones/hydroquinones. Several compounds have shown IC50 values under the mu M level. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10007-4

文献信息

• Synthesis and bioactivity of new antineoplastic terpenylquinones
  作者：Marina Gordaliza、JoséMa Miguel del Corral、Ma Angeles Castro、Ma Mar Mahiques、MaDolores García-Grávalos、Arturo San Feliciano

  DOI：10.1016/0960-894x(96)00326-5

  日期：1996.8

  Several monoterpenylquinones have been prepared and evaluated for their cytotoxic activity against four cell lines cultures. The size of the quinone fragment is important for the activity, being the naphtalene derivatives the most potent compounds tested. The presence of substituents on the quinone ring decreases the potency but increases the selectivity. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones
  作者：José M. Miguel del Corral、Maria Angeles Castro、Marina Gordaliza、Maria Luz Martin、Alaide B. Oliveira、Simone A. Gualberto、Maria Dolores García-Grávalos、Arturo San Feliciano

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

  日期：2002.12

  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.
• Further antineoplastic terpenylquinones and terpenylhydroquinones
  作者：JoséM. Miguel del Corral、Marina Gordaliza、M. Angeles Castro、M.Mar Mahiques、Arturo San Feliciano、M.Dolores García-Grávalos

  DOI：10.1016/s0968-0896(97)10007-4

  日期：1998.1

  Influences of the quinone/hydroquinone fragment and other structural features are considered in relation with the antineoplastic activity and selectivity of terpenylquinones/hydroquinones. Several compounds have shown IC50 values under the mu M level. (C) 1998 Elsevier Science Ltd. All rights reserved.