3-[[1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]-5-methoxy-1,2-dimethylindole-4,7-dione | 1192744-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[[1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]-5-methoxy-1,2-dimethylindole-4,7-dione
• 英文别名: 3-[[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]-5-methoxy-1,2-dimethylindole-4,7-dione
• CAS: 1192744-27-6
• 化学式: C₁₆H₁₂F₉NO₄
• 分子量: 453.261
• InChiKey: ZRVGPXMPWDGUOS-UHFFFAOYSA-N

物化性质

• 熔点：
  207-210 °C
• 沸点：
  450.3±45.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-[[1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]-5-methoxy-1,2-dimethylindole-4,7-dione 在 NADPH:cytochrome P₄₅₀ reductase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 water-d2 、 水 、 乙腈 为溶剂， 反应 0.25h， 生成 高氟叔丁醇
  参考文献：
  名称：

  Monitoring of Biological One-Electron Reduction by ¹⁹F NMR Using Hypoxia Selective Activation of an ¹⁹F-Labeled Indolequinone Derivative

  摘要：

  Biological reduction of fluorine-labeled indolequinone derivative (IQ-F) was characterized by F-19 NMR for quantitative molecular understanding. The chemical shift change in F-19 NMR allowed monitoring of the enzymatic reduction of IQ-F. Upon hypoxic treatment of IQ-F with NADPH:cytochrome P450 reductase, IQ-F was activated via catalytic one-electron reduction to release nonafluoro-tert-butyl alcohol (F-OH), while the formation of F-OH was significantly suppressed under aerobic conditions. Similar hypoxia-selective reduction of IQ-F occurred within A549 cells, which expresses NADPH:cytochrome P450 reductase. The kinetic analysis was also performed to propose a reaction mechanism. The molecular oxygen slightly prevents the binding of IQ-F to reductase, while the rate of net reaction was decreased due to oxidation of a semiquinone anion radical intermediate generated by one-electron reduction of IQ-F. The disappearance of IQ-F and appearance of F-OH were imaged by F-19 fast spin echo, thus visualizing the hypoxia-selective reduction of IQ-F by means of MR imaging.

  DOI：

  10.1021/ja904953b
• 作为产物：
  描述：

  高氟叔丁醇 、 3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 以15%的产率得到3-[[1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]-5-methoxy-1,2-dimethylindole-4,7-dione
  参考文献：
  名称：

  Monitoring of Biological One-Electron Reduction by ¹⁹F NMR Using Hypoxia Selective Activation of an ¹⁹F-Labeled Indolequinone Derivative

  摘要：

  Biological reduction of fluorine-labeled indolequinone derivative (IQ-F) was characterized by F-19 NMR for quantitative molecular understanding. The chemical shift change in F-19 NMR allowed monitoring of the enzymatic reduction of IQ-F. Upon hypoxic treatment of IQ-F with NADPH:cytochrome P450 reductase, IQ-F was activated via catalytic one-electron reduction to release nonafluoro-tert-butyl alcohol (F-OH), while the formation of F-OH was significantly suppressed under aerobic conditions. Similar hypoxia-selective reduction of IQ-F occurred within A549 cells, which expresses NADPH:cytochrome P450 reductase. The kinetic analysis was also performed to propose a reaction mechanism. The molecular oxygen slightly prevents the binding of IQ-F to reductase, while the rate of net reaction was decreased due to oxidation of a semiquinone anion radical intermediate generated by one-electron reduction of IQ-F. The disappearance of IQ-F and appearance of F-OH were imaged by F-19 fast spin echo, thus visualizing the hypoxia-selective reduction of IQ-F by means of MR imaging.

  DOI：

  10.1021/ja904953b

文献信息

• Monitoring of Biological One-Electron Reduction by ¹⁹F NMR Using Hypoxia Selective Activation of an ¹⁹F-Labeled Indolequinone Derivative
  作者：Kazuhito Tanabe、Hiroshi Harada、Michiko Narazaki、Kazuo Tanaka、Kenichi Inafuku、Hirokazu Komatsu、Takeo Ito、Hisatsugu Yamada、Yoshiki Chujo、Tetsuya Matsuda、Masahiro Hiraoka、Sei-ichi Nishimoto

  DOI：10.1021/ja904953b

  日期：2009.11.11

  Biological reduction of fluorine-labeled indolequinone derivative (IQ-F) was characterized by F-19 NMR for quantitative molecular understanding. The chemical shift change in F-19 NMR allowed monitoring of the enzymatic reduction of IQ-F. Upon hypoxic treatment of IQ-F with NADPH:cytochrome P450 reductase, IQ-F was activated via catalytic one-electron reduction to release nonafluoro-tert-butyl alcohol (F-OH), while the formation of F-OH was significantly suppressed under aerobic conditions. Similar hypoxia-selective reduction of IQ-F occurred within A549 cells, which expresses NADPH:cytochrome P450 reductase. The kinetic analysis was also performed to propose a reaction mechanism. The molecular oxygen slightly prevents the binding of IQ-F to reductase, while the rate of net reaction was decreased due to oxidation of a semiquinone anion radical intermediate generated by one-electron reduction of IQ-F. The disappearance of IQ-F and appearance of F-OH were imaged by F-19 fast spin echo, thus visualizing the hypoxia-selective reduction of IQ-F by means of MR imaging.