2-butylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione | 1213299-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-butylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione
• 英文别名: 2-(n-butylamino)-3,5,6,7,8-pentafluoro-1,4-naphthoquinone；2-n-butylaminopentafluoro-1,4-naphthoquinone；2-(Butylamino)pentafluoro-1,4-naphthoquinone；2-(butylamino)-3,5,6,7,8-pentafluoronaphthalene-1,4-dione
• CAS: 1213299-21-8
• 化学式: C₁₄H₁₀F₅NO₂
• 分子量: 319.231
• InChiKey: ZJCVRTKTDXWTAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-butylamino-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione 、 乙胺氢溴酸盐 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以63%的产率得到2-n-butylamino-6-ethylaminotetrafluoro-1,4-naphthoquinone
  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
• 作为产物：
  描述：

  hexafluoro-1,4-naphthoquinone 、 正丁胺 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以63%的产率得到2-butylamino-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

文献信息

• 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.
• 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.
• Cytotoxicity of new n-butylamino and sulfur-containing derivatives of polyfluorinated 1,4-naphthoquinone
  作者：Ol'ga A. Zakharova、Leonid I. Goryunov、Nadezhda M. Troshkova、Ludmila P. Ovchinnikova、Vitalij D. Shteingarts、Georgy A. Nevinsky

  DOI：10.1016/j.ejmech.2009.10.006

  日期：2010.1

  Four new n-butylamino and two sulfur-containing derivatives of polyfluoro-1,4-naphthoquinone were synthesized and their mutagenic and antioxidant properties in Salmonella cells, as well as the cytotoxicity in human myeloma (RPMI 8226), human mammary adenocarcinoma (MCF-7), mouse fibroblasts (LMTK) and primary mouse fibroblast cells (PMF) were studied. 2-n-Butylamino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (1) showed efficient inhibition of the growth of the tumor cells. 2,8-Di-(n-butylamino )-3,5,6,7-tetrafluoro-1,4-naphthoquinone (2) had significantly less growth-inhibiting properties, while 2,6-di-(n-butylamino)-3,5,7,8-tetrafluoro-1,4-naphthoquinone (3) and 2,6,8-tri-(n-butylamino)-3,5,7-tetrafluoro-1,4-naphthoquinone (4), demonstrated very low cytotoxicity. Compounds 1 and 2 were remarkably less cytotoxic while compound 3 and 4 were not cytotoxic toward LMTK and PMF cells as compared with tumor human cell lines. Cytotoxicity of 2-(2'-methylthioethyl)amino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (5) and (2,2'-dithiodi-2)-3,5,6,7,8-pentafluoro-1,4-naphthoquinone-2-ylamino)ethan (6) toward mammalian cells was compared with that for compounds 1 and 2. (C) 2009 Elsevier Masson SAS. All rights reserved.