2-methoxypentafluoro-1,4-naphthoquinone | 20927-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxypentafluoro-1,4-naphthoquinone
• 英文别名: 2-Methoxy-3,5,6,7,8-pentafluor-naphtochinon-(1,4)；2-methoxy-3,5,6,7,8-pentafluoro-1,4-dihydronaphthalene-1,4-dione；2-methoxy-3,5,6,7,8-pentafluoro-1,4-naphthoquinone；3,5,6,7,8-pentafluoro-2-methoxy-1,4-naphthoquinone；2,5,6,7,8-pentafluoro-3-methoxynaphthalene-1,4-dione
• CAS: 20927-19-9
• 化学式: C₁₁H₃F₅O₃
• 分子量: 278.135
• InChiKey: CNYZGMWVWZKLQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethylimidazolin-1-oxyl-3-oxide 、 2-methoxypentafluoro-1,4-naphthoquinone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到2-(3,5,6,7,8-pentafluoro-1-hydroxy-2-methoxy-4-oxo-1,4-dihydronaphthalen-1-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl
  参考文献：
  名称：

  锂化硝酰基硝基氮氧化物与多氟1,4-萘醌的相互作用

  摘要：

  发现4,4,5,5-四甲基-4,5-二氢-1 H-咪唑-3-氧化物-1-氧基锂衍生物与2-甲氧基五氟-1,4-萘醌反应生成羰基官能团上的加成：2-（3,5,6,7,8-五氟-1-羟基-2-甲氧基-4-氧代-1,4-二氢萘-1-基）-4,4,5 ，5-四甲基-4，5-二氢-1 H-咪唑-3-氧化物-1-氧基。加成产物的产率随温度增加而在0℃达到84％。锂衍生物与六氟-1,4-萘醌的反应在两个羰基上产生加成产物，即亚硝酰基硝基氧双自由基2,3,5,6,7,8-六氟-1,4-双（4,4,5,5-四甲基-3-氧化物-1-氧基-4,5-二氢-1 H-咪唑-2-基）-1,4-二氢萘-1,4-二醇的产率为16％。通过X射线衍射分析来解析单自由基和双自由基的结构，这揭示了在OH基团和一氧化氮之间形成分子内的H键。根据电子顺磁共振（EPR）光谱，所获得的一氧化氮和二氧化氮在甲苯溶液中易于自发脱氧，从而得到相

  DOI：

  10.1016/j.tet.2018.05.075
• 作为产物：
  描述：

  甲醇 、 hexafluoro-1,4-naphthoquinone 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 216.0h， 以65%的产率得到2-methoxypentafluoro-1,4-naphthoquinone
  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

• Cytotoxicity of new polyfluorinated 1,4-naphtoquinones with diverse substituents in the quinone moiety
  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.bmc.2010.11.027

  日期：2011.1

  Fluorinated derivatives of 1,4-naphthoquinones are highly potent inhibitors of Cdc25A and Cdc25B phosphatases and growth of tumor cells. Eight new derivatives of polyfluoro-1,4-naphthoquinone were synthesized and their cytotoxicity in human myeloma, human mammary adenocarcinoma, mouse fibroblasts and primary mouse fibroblast cells as well as their mutagenic and antioxidant properties in a Salmonella

  1,4-萘醌的氟化衍生物是Cdc25A和Cdc25B磷酸酶和肿瘤细胞生长的高效抑制剂。合成了八种新的多氟-1,4-萘醌衍生物，研究了它们在人骨髓瘤，人乳腺腺癌，小鼠成纤维细胞和原代小鼠成纤维细胞中的细胞毒性，以及它们在沙门氏菌测试菌株中的诱变和抗氧化特性。抑制两株肿瘤细胞生长的效率依次降低：2-（2-羟基-乙基氨基）-3,5,6,7,8-五氟-1,4-萘醌（1），2， 3-二甲氧基-5,6,7,8-四氟-1,4-萘醌（2），2- [2-羟乙基（甲基）氨基] -3,5,6,7,8-五氟-1,4 -萘醌（3），2-吗啉代-3,5,6,7,8-五氟-1,4-萘醌（4），2- [双-（2-羟乙基）氨基] -3,5,6,7,8-五氟-1,4-萘醌（5），2-[（（2-羟基）乙基硫基）]-5,6,7,8-四氟-1,4-萘醌（6），2-甲氧基-3,5， 6,7,8-五氟-1,4-萘醌（7）和1,4-二氧-3-（1-吡啶基）-1
• 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.
• Interaction of a lithiated nitronyl nitroxide with polyfluorinated 1,4-naphthoquinones
  作者：S.I. Zhivetyeva、I.A. Zayakin、I.Yu. Bagryanskaya、E.V. Zaytseva、E.G. Bagryanskaya、E.V. Tretyakov

  DOI：10.1016/j.tet.2018.05.075

  日期：2018.7

  and reached 84% at 0 °C. The reaction of the lithium derivative with hexafluoro-1,4-naphthoquinone gave rise to a product of addition at both carbonyl groups, namely, nitronyl nitroxide diradical 2,3,5,6,7,8-hexafluoro-1,4-bis(4,4,5,5-tetramethyl-3-oxide-1-oxyl-4,5-dihydro-1H-imidazole-2-yl)-1,4-dihydronaphthalene-1,4-diol in a 16% yield. The structures of both mono- and diradical were solved by X-ray

  发现4,4,5,5-四甲基-4,5-二氢-1 H-咪唑-3-氧化物-1-氧基锂衍生物与2-甲氧基五氟-1,4-萘醌反应生成羰基官能团上的加成：2-（3,5,6,7,8-五氟-1-羟基-2-甲氧基-4-氧代-1,4-二氢萘-1-基）-4,4,5 ，5-四甲基-4，5-二氢-1 H-咪唑-3-氧化物-1-氧基。加成产物的产率随温度增加而在0℃达到84％。锂衍生物与六氟-1,4-萘醌的反应在两个羰基上产生加成产物，即亚硝酰基硝基氧双自由基2,3,5,6,7,8-六氟-1,4-双（4,4,5,5-四甲基-3-氧化物-1-氧基-4,5-二氢-1 H-咪唑-2-基）-1,4-二氢萘-1,4-二醇的产率为16％。通过X射线衍射分析来解析单自由基和双自由基的结构，这揭示了在OH基团和一氧化氮之间形成分子内的H键。根据电子顺磁共振（EPR）光谱，所获得的一氧化氮和二氧化氮在甲苯溶液中易于自发脱氧，从而得到相