2-chloro-3-cyclohexylnaphthalene-1,4-dione | 83570-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-cyclohexylnaphthalene-1,4-dione
• 英文别名: 2-chloro-3-cyclohexyl-[1,4]naphthoquinone；2-Chlor-3-cyclohexyl-[1,4]naphthochinon；2-cyclohexyl-3-chloro-1,4-naphthoquinone；2-cyclohexyl-3-chloronaphthoquinone；Cyclohexyl-chloro-naphthoquinone
• CAS: 83570-32-5
• 化学式: C₁₆H₁₅ClO₂
• 分子量: 274.747
• InChiKey: OYFJINWSAOBOQX-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  400.9±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  2-chloro-3-cyclohexylnaphthalene-1,4-dione 生成 帕伐醌
  参考文献：
  名称：

  Hudson; Pether; Randall, European Journal of Medicinal Chemistry, 1986, vol. 21, # 4, p. 271 - 275

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 环己甲酸 在 ammonium peroxydisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 以13%的产率得到2-chloro-3-cyclohexylnaphthalene-1,4-dione
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v

文献信息

• Preparation of 2-alkyl-1,4-naphthoquinones
  作者：William G. Peet、Wilson Tam

  DOI：10.1039/c39830000853

  日期：——

  The reaction of 2,3-dichloro-1,4-naphthoquinone with organo aluminium, zinc, zirconium, or tin reagents yields 2-alkyl-3-chloro-1,4-naphthoquinones; with Zr or Sn reagents, palladium or nickel catalyst is needed.

  2,3-二氯-1,4-萘醌与有机铝，锌，锆或锡试剂的反应生成2-烷基-3-氯-1,4-萘醌；使用Zr或Sn试剂时，需要钯或镍催化剂。
• PREPARATION OF NAPHTHOQUINONE COMPOUNDS USING 2,3-DIHALONAPHTHOQUINONE
  申请人：Saralya Sanjay Sukumar

  公开号：US20110004024A1

  公开（公告）日：2011-01-06

  The present invention relates the use of 2,3-dihalonaphthoquinone compounds of Formula I wherein R 1 and R 2 are leaving groups like halogens selected from the group comprising Cl, Br, I and F and the R 1 and R 2 may be the same halogen or may contain different halogen groups, or sulphonyl groups, for making napthoquinone compounds of Formula IA wherein X is any aryl, heteroaryl, alkyl, cyclohexyl, substituted cylohexyl groups and the like.

  本发明涉及使用式I中的2,3-二卤代萘醌化合物，其中R1和R2是离去基团，如从包括Cl、Br、I和F的卤族中选择的卤素，且R1和R2可以是相同的卤素或含有不同的卤素基团或磺酰基团，以制备式IA中的萘醌化合物，其中X是任何芳基、杂环芳基、烷基、环己基、取代环己基等。
• Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177
  作者：Fieser et al.

  DOI：——

  日期：——
• Synthesis of atovaquone
  作者：David R. Williams、Michael P. Clark

  DOI：10.1016/s0040-4039(98)01691-8

  日期：1998.10

  A short synthesis of atovaquone 1 is achieved via the radical coupling of the trans-1,4-sbustituted cyclohexyl mono-oxalate 2 and 2-chloronapthoquinone under phase transfer conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.
• [EN] PREPARATION OF NAPHTHOQUINONE COMPOUNDS USING 2, 3-DIHALONAPTHOQUINONE<br/>[FR] PRÉPARATION DE COMPOSÉS NAPHTOQUINONE EN UTILISANT DE LA 2,3-DIHALONAPHTOQUINONE
  申请人：ALKEM LAB LTD

  公开号：WO2009122432A3

  公开（公告）日：2010-08-26