2-(4'-chlorobenzoyl)-1,4-naphthoquinone | 854486-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4'-chlorobenzoyl)-1,4-naphthoquinone
• 英文别名: 2-(4-Chlorobenzoyl)naphthalene-1,4-dione；2-(4-chlorobenzoyl)naphthalene-1,4-dione
• CAS: 854486-31-0
• 化学式: C₁₇H₉ClO₃
• 分子量: 296.71
• InChiKey: CCEURSGWRKIMNI-UHFFFAOYSA-N

物化性质

• 沸点：
  468.5±45.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-chlorobenzoyl)-1,4-naphthoquinone 在 manganese triacetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 15.17h， 生成 3-chloro-12-hydroxy-6,11-dioxo-6,11-dihydronaphthacene-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  2-(乙氧羰基甲基)-1,4-萘醌衍生物的氧化自由基环化

  摘要：

  描述了锰 (III) 介导的 2-(乙氧基羰基甲基)-1,4-萘醌衍生物的氧化自由基环化。这些起始的2-(乙氧基羰基甲基)-1,4-萘醌可以通过相应的1,4-萘醌与硝基乙酸乙酯的反应有效合成。以2-苄基-3-(乙氧基羰基甲基)-1,4-萘醌为原料，高效生产并高选择性的5,12-并四苯。使用乙基 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones，除了预期的 6-hydroxynaphthacene-5,12-diones，新型萘并[2,3-c]furan-4,9-diones也形成了主打产品。

  DOI：

  10.1055/s-2005-861850
• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 在 ammonium cerium (IV) nitrate 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 19.0h， 生成 2-(4'-chlorobenzoyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells

  摘要：

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.048

文献信息

• A novel manganese(iii) acetate mediated reaction between 2-benzoyl-1,4-naphthoquinones and 1,3-dicarbonyl compounds
  作者：Chien-Yu Lin、Yu-Chih Cheng、An.-I. Tsai、Che-Ping Chuang

  DOI：10.1039/b516285h

  日期：——

  A manganese(III)-mediated reaction between 2-benzoyl-1,4-naphthoquinones and 1,3-dicarbonyl compounds is described. This reaction provides an effective method for the synthesis of naphtho[2,3-c]furan-4,9-diones and naphthacene-5,12-diones, and it shows fair to high chemoselectivity depending on the electronic effect of the benzoyl group substituent on the reactants. With ethyl benzoylacetate and 1

  描述了2-苯甲酰基-1,4-萘醌与1,3-二羰基化合物之间的锰（III）介导的反应。该反应提供了一种合成萘并[2,3-c]呋喃-4,9-二酮和萘并5,12-二酮的有效方法，并且根据苯甲酰基的电子效应，其显示出中等至高的化学选择性。反应物上的取代基。用苯甲酰乙酸乙酯和1，3-二酮，可以高效，高选择性地生产新型萘并[2,3-c]呋喃-4,9-二酮。
• 1,4-NAPHTHOQUINONE DERIVATIVES AND THERAPEUTIC USE THEREOF
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2257515B1

  公开（公告）日：2017-05-17
• US9090549B2
  申请人：——

  公开号：US9090549B2

  公开（公告）日：2015-07-28
• Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells
  作者：Suthananda N. Sunassee、Clinton G.L. Veale、Nelusha Shunmoogam-Gounden、Omalaja Osoniyi、Denver T. Hendricks、Mino R. Caira、Jo-Anne de la Mare、Adrienne L. Edkins、Antônio V. Pinto、Eufrânio N. da Silva Júnior、Michael T. Davies-Coleman

  DOI：10.1016/j.ejmech.2012.12.048

  日期：2013.4

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Oxidative Free Radical Cyclization of 2-(Ethoxycarbonylmethyl)-1,4-naphthoquinone Derivatives
  作者：Che-Ping Chuang、Hui-Li Chen、Chien-Yu Lin、Yu-Chih Cheng、An-I Tsai

  DOI：10.1055/s-2005-861850

  日期：——

  A manganese(III)-mediated oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4-naphthoquinone derivatives is described. These starting 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones can be synthesized effectively from the reaction of corresponding 1,4-naphthoquinones with ethyl nitroacetate. With 2-benzyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, naphthacene-5,12-diones were produced

  描述了锰 (III) 介导的 2-(乙氧基羰基甲基)-1,4-萘醌衍生物的氧化自由基环化。这些起始的2-(乙氧基羰基甲基)-1,4-萘醌可以通过相应的1,4-萘醌与硝基乙酸乙酯的反应有效合成。以2-苄基-3-(乙氧基羰基甲基)-1,4-萘醌为原料，高效生产并高选择性的5,12-并四苯。使用乙基 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones，除了预期的 6-hydroxynaphthacene-5,12-diones，新型萘并[2,3-c]furan-4,9-diones也形成了主打产品。