6-(4-methyl-pentyl)-[1,4]naphthoquinone | 443888-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(4-methyl-pentyl)-[1,4]naphthoquinone
• 英文别名: 6-(4-Methylpentyl)naphthalene-1,4-dione
• CAS: 443888-97-9
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: IQSOIJVOZDIZMW-UHFFFAOYSA-N

物化性质

• 沸点：
  389.8±42.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 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：

  6-(4-methyl-pentyl)-[1,4]naphthoquinone 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-(p-acetoxyanilino)-6-(4-methylpentyl)-[1,4]-naphthoquinone
  参考文献：
  名称：

  新的氨基萜烯醌的合成和细胞毒性。

  摘要：

  通过单萜α-月桂烯和对苯醌之间的环加成反应，已经制备了几种6（7）-烷基-1,4-萘醌（NQ），并且在C-2位引入了卤素和含氮官能团。萘醌环通过亲核加成或取代反应。NQ位置2/3处的这些取代基明显影响此类化合物的细胞毒性。特别令人感兴趣的是被芳基氨基，特别是对-氧芳基氨基，基团取代，其大大增强了它们的生物活性和选择性。

  DOI：

  10.1016/j.bmc.2004.10.059
• 作为产物：
  描述：

  月桂烯 在 Lindlar's catalyst 、 三氟化硼乙醚 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 36.0h， 生成 6-(4-methyl-pentyl)-[1,4]naphthoquinone
  参考文献：
  名称：

  萜烯-1,4-萘醌和1,4-蒽二酮衍生物的合成及抗真菌活性

  摘要：

  进行的27简单和杂环稠合的异戊烯基-1,4-萘醌和1,4-蒽二酮类抗真菌评价体外针对人病原性酵母菌（念珠菌属）和丝状真菌（曲霉属，镰孢属，和毛癣菌属）。最初用于获得醌衍生物的合成策略是基于月桂烯和几种对映体之间的Diels-Alder环加成反应-苯醌衍生物，在蒽-1,4-二酮的情况下，异戊二烯侧链的环化。MIC值在低μg/ mL范围内的最有希望的化合物是那些带有一个或两个氯原子连接在醌环上的化合物。确定的最有效化合物的时间杀灭曲线显示出其抑菌作用模式与伊曲康唑相似。

  DOI：

  10.1016/j.ejmech.2013.06.018

文献信息

• 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.
• 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.
• Synthesis and cytotoxicity of new heterocyclic terpenylnaphthoquinones
  作者：José M. Miguel del Corral、M Angeles Castro、Marina Gordaliza、M Luz Martín、Ana M Gamito、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1016/j.bmc.2005.12.002

  日期：2006.4

  Several 2-arylamino-, 2-aryloxy- and 2-arylsulfinyl-6(7)-alkyl-1.4-naphthoquinones (NQ) have been prepared and further transformed into the corresponding heterocyclic-fused naphthoquinones by palladium (II)-catalyzed oxidative cyclization. The Compounds synthesized have been evaluated against neoplastic cell lines. The extension of the polycyclic system clearly decreased the cytotoxic potency of the 2-substituted terpenylnaphthoquinones. (c) 2005 Elsevier Ltd. All rights reserved.
• COMPOUND FOR ORGANIC THIN FILM TRANSISTOR AND ORGANIC THIN FILM TRANSISTOR USING THE SAME
  申请人：Nakano Yuki

  公开号：US20110210319A1

  公开（公告）日：2011-09-01

  A compound for an organic thin film transistor represented by the following formula ( 1 ): wherein at least one pair of adjacent two groups of R 1 , R 3 , R 5 and R 7 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 3 to 60 carbon atoms, the ring being fused to the ring to which the groups are bonded; and at least one pair of adjacent two groups of R 2 , R 4 , R 6 and R 8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 3 to 60 carbon atoms, the ring being fused to the ring to which the groups are bonded.
• US8785915B2
  申请人：——

  公开号：US8785915B2

  公开（公告）日：2014-07-22