2-diethylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione | 1217482-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-diethylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione
• 英文别名: 2-diethylaminopentafluoro-1,4-naphthoquinone；2-diethylamino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone；2-(Diethylamino)-3,5,6,7,8-pentafluoronaphthalene-1,4-dione
• CAS: 1217482-68-2
• 化学式: C₁₄H₁₀F₅NO₂
• 分子量: 319.231
• InChiKey: FCTPTKUASMUBKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-diethylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione 以 1,4-二氧六环 、 水 为溶剂， 反应 552.0h， 以39%的产率得到2-ethylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of 2-aminopentafluoro-1,4-naphthoquinone derivatives

  摘要：

  Potential biologically active derivatives of 2-aminopentafluoro-1,4-naphthoquinone modified at the amino group were synthesized in 32-96% yield by reactions of hexafluoro-1,4-naphthoquinone with nitrogen-centered nucleophiles.

  DOI：

  10.1134/s1070428009060050
• 作为产物：
  描述：

  hexafluoro-1,4-naphthoquinone 、 二乙胺 以 二甲基亚砜 为溶剂， 生成 2-diethylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione
  参考文献：
  名称：

  Aminodefluorination of 2-X-pentafluoro-1,4-naphthoquinones (X = NH Bu, NEt2, and OMe)

  摘要：

  Aminodefluorination of 2-n-butylamino- and 2-diethylaminopentafluoro-1,4-naphthoquinone by alkylamines (HNRR2)-R-1 ((NRR2)-R-1 = NHEt, (NHBu)-Bu-n and NEt2) occurs at the 6- or 8-position and further, accordingly, at the 8- or at one of the 5- and 6-sites. The isomer ratio changes significantly in favor of a beta-replacement product with solvent variation in the sequence: toluene < 1,4-dioxane < DMSO. n-Butylaminodefluorination of 2-methoxypentafluoro-1,4-naphthoquinone gives mixtures of fluorine substitution products both on the benzene and quinone rings. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.10.007

文献信息

• 2-DIETHYLAMINOVINYL DERIVATIVES OF HALOGENATED 1,4-QUINONES: SYNTHETIC AND STRUCTURAL ASPECTS
  作者：S. I. Zhivetyeva、I. A. Zayakin、I. Yu. Bagryanskaya、E. V. Tretyakov

  DOI：10.1134/s0022476620080107

  日期：2020.8

  Diethylaminovinyl derivatives of halogenated 1,4-quinones (enaminoquinones) are produced by the interaction of halogenated 1,4-quinones with N,N-diethyl-N-vinylamine obtained in situ from Et2NH and MeCHO. Molecular and crystal structures of enaminoquinones halogenated in the quinone fragment are determined. It is shown that in the solid phase, atoms of the entire push-pull system of enaminoquinones

  卤化 1,4-醌（烯氨基醌）的二乙基氨基乙烯基衍生物是通过卤化 1,4-醌与从 Et2NH 和 MeCHO 原位获得的 N,N-二乙基-N-乙烯基胺相互作用产生的。确定了醌片段中卤化的烯氨基醌的分子和晶体结构。结果表明，在固相中，烯氨基醌的整个推拉系统的原子实际上位于一个平面内。
• Aminodefluorination of 2-X-pentafluoro-1,4-naphthoquinones (X = NH Bu, NEt2, and OMe)
  作者：Nadezhda M. Troshkova、Leonid I. Goryunov、Yurij V. Gatilov、Georgy A. Nevinsky、Vitalij D. Shteingarts

  DOI：10.1016/j.jfluchem.2009.10.007

  日期：2010.1

  Aminodefluorination of 2-n-butylamino- and 2-diethylaminopentafluoro-1,4-naphthoquinone by alkylamines (HNRR2)-R-1 ((NRR2)-R-1 = NHEt, (NHBu)-Bu-n and NEt2) occurs at the 6- or 8-position and further, accordingly, at the 8- or at one of the 5- and 6-sites. The isomer ratio changes significantly in favor of a beta-replacement product with solvent variation in the sequence: toluene < 1,4-dioxane < DMSO. n-Butylaminodefluorination of 2-methoxypentafluoro-1,4-naphthoquinone gives mixtures of fluorine substitution products both on the benzene and quinone rings. (C) 2009 Elsevier B.V. All rights reserved.
• Synthesis of 2-aminopentafluoro-1,4-naphthoquinone derivatives
  作者：L. I. Goryunov、N. M. Troshkova、G. A. Nevinskii、V. D. Shteingarts

  DOI：10.1134/s1070428009060050

  日期：2009.6

  Potential biologically active derivatives of 2-aminopentafluoro-1,4-naphthoquinone modified at the amino group were synthesized in 32-96% yield by reactions of hexafluoro-1,4-naphthoquinone with nitrogen-centered nucleophiles.
• Cytotoxicity of new alkylamino- and phenylamino-containing polyfluorinated derivatives of 1,4-naphthoquinone
  作者：Ol'ga D. Zakharova、Ludmila P. Ovchinnikova、Leonid I. Goryunov、Nadezhda M. Troshkova、Vitalij D. Shteingarts、Georgy A. Nevinsky

  DOI：10.1016/j.ejmech.2010.02.009

  日期：2010.6

  Fluorinated derivatives of 1,4-naphthoquinone are highly potent inhibitors of Cdc25A and Cdc25 phosphatases and growth of tumor cells. Five new N-substituted polyfluorinated derivatives of 2-amino-1,4-naphthoquinone were synthesized and their mutagenic and antioxidant properties in Salmonella cells, as well as cytotoxicity in human myeloma (RPMI 8226), human mammary adenocarcinoma (MCF-7), mouse fibroblasts (LMTK) and primary mouse fibroblast cells (PMF) were studied 2-tert-Butylamino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (1) inhibited the growth of normal control and tumor cells at the same concentration. Three compounds: 2-diethylamino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (2), 2-ethylamino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (3), 2-phenylamino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (4) exhibited a 50% decrease in the growth of cancer cells at low and comparable concentrations (2 4-8 6 mu M) while being remarkably less cytotoxic toward normal LMTK and PMF cells. Quinones (1)-(4), but not 2-phenylamino-3-methyl-5,6,7,8-tetrafluoro-1,4-naphthoquinone (5), efficiently suppressed spontaneous mutagenesis in Salmonella cells, while all compounds 1-5 decreased the mutagenic effect of H2O2 on bacterial cells. Their possible perspectives as anticancer drugs are shortly discussed.