8,9,10,11-tetrafluoro-6,13-bis[(tripropan-2-ylsilyl)ethynyl]-5,14-dihydroquinoxalino[2,3-b]phenazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8,9,10,11-tetrafluoro-6,13-bis[(tripropan-2-ylsilyl)ethynyl]-5,14-dihydroquinoxalino[2,3-b]phenazine
• 化学式: C₄₀H₄₈F₄N₄Si₂
• 分子量: 717.013
• InChiKey: KBSLXZOHLJOXGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.28
• 重原子数：
  50.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.84
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8,9,10,11-tetrafluoro-6,13-bis[(tripropan-2-ylsilyl)ethynyl]-5,14-dihydroquinoxalino[2,3-b]phenazine 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以92%的产率得到1,2,3,4-tetrafluoro-6,13-bis[(tripropan-2-ylsilyl)ethynyl]quinoxalino[2,3-b]phenazine
  参考文献：
  名称：

  Partially Fluorinated Tetraazaacenes by Nucleophilic Aromatic Substitution

  摘要：

  We report the sodium hydride-mediated reactions of a diethynylated diaminophenazine with perfluorobenzene, perfluoronaphthalene, and two octafluoroanthracene derivatives. In all of the cases, an N,N-dihydropyrazine ring is formed, and partially fluorinated tetraazapentacenes, tetraazahexacenes, and tetraazaheptacenes (in their respective N,N-dihydro forms) are easily prepared. In the case of the dihydrotetraazapentacenes and -hexacenes, oxidation with manganese dioxide is possible to give the desired, fully unsaturated tetraazaacenes; two molecules of the azahexacene undergo a Diels-Alder reaction in which an alkyne substituent in the conserved hexacene unit works as the dienophile while the tetraazahexacene participates as the diene to give an unsymmetrical dimer. All of the coupling targets were investigated by NMR and UV-vis spectroscopies, and several single-crystal structures of the N,N-dihydrotetraazaacenes and also that of the tetrafluorotetraazaacene were obtained.

  DOI：

  10.1021/jo401824g
• 作为产物：
  描述：

  六氟苯 、 1,4-bis((triisopropylsilyl)ethynyl)phenazine-2,3-diamine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以31%的产率得到8,9,10,11-tetrafluoro-6,13-bis[(tripropan-2-ylsilyl)ethynyl]-5,14-dihydroquinoxalino[2,3-b]phenazine
  参考文献：
  名称：

  Partially Fluorinated Tetraazaacenes by Nucleophilic Aromatic Substitution

  摘要：

  We report the sodium hydride-mediated reactions of a diethynylated diaminophenazine with perfluorobenzene, perfluoronaphthalene, and two octafluoroanthracene derivatives. In all of the cases, an N,N-dihydropyrazine ring is formed, and partially fluorinated tetraazapentacenes, tetraazahexacenes, and tetraazaheptacenes (in their respective N,N-dihydro forms) are easily prepared. In the case of the dihydrotetraazapentacenes and -hexacenes, oxidation with manganese dioxide is possible to give the desired, fully unsaturated tetraazaacenes; two molecules of the azahexacene undergo a Diels-Alder reaction in which an alkyne substituent in the conserved hexacene unit works as the dienophile while the tetraazahexacene participates as the diene to give an unsymmetrical dimer. All of the coupling targets were investigated by NMR and UV-vis spectroscopies, and several single-crystal structures of the N,N-dihydrotetraazaacenes and also that of the tetrafluorotetraazaacene were obtained.

  DOI：

  10.1021/jo401824g

文献信息

• Partially Fluorinated Tetraazaacenes by Nucleophilic Aromatic Substitution
  作者：Jens U. Engelhart、Benjamin D. Lindner、Olena Tverskoy、Frank Rominger、Uwe H. F. Bunz

  DOI：10.1021/jo401824g

  日期：2013.11.1

  We report the sodium hydride-mediated reactions of a diethynylated diaminophenazine with perfluorobenzene, perfluoronaphthalene, and two octafluoroanthracene derivatives. In all of the cases, an N,N-dihydropyrazine ring is formed, and partially fluorinated tetraazapentacenes, tetraazahexacenes, and tetraazaheptacenes (in their respective N,N-dihydro forms) are easily prepared. In the case of the dihydrotetraazapentacenes and -hexacenes, oxidation with manganese dioxide is possible to give the desired, fully unsaturated tetraazaacenes; two molecules of the azahexacene undergo a Diels-Alder reaction in which an alkyne substituent in the conserved hexacene unit works as the dienophile while the tetraazahexacene participates as the diene to give an unsymmetrical dimer. All of the coupling targets were investigated by NMR and UV-vis spectroscopies, and several single-crystal structures of the N,N-dihydrotetraazaacenes and also that of the tetrafluorotetraazaacene were obtained.