(2E,6E)-2-[(Z)-3-(dimethylamino)-2-fluoroprop-2-enylidene]-6-[(E)-3-(dimethylamino)prop-2-enylidene]cyclohexan-1-one | 121722-86-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2E,6E)-2-[(Z)-3-(dimethylamino)-2-fluoroprop-2-enylidene]-6-[(E)-3-(dimethylamino)prop-2-enylidene]cyclohexan-1-one
• CAS: 121722-86-9
• 化学式: C₁₆H₂₃FN₂O
• 分子量: 278.37
• InChiKey: ACRUQUVXYNUOIB-DEDZWUKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2E,6E)-2-[(Z)-3-(dimethylamino)-2-fluoroprop-2-enylidene]-6-[(E)-3-(dimethylamino)prop-2-enylidene]cyclohexan-1-one 以 异丙醇 为溶剂， 生成 {8-[(E)-3-Dimethylamino-prop-2-en-(E)-ylidene]-3-fluoro-6,7,8,8a-tetrahydro-5H-chromen-2-yl}-dimethyl-amine
  参考文献：
  名称：

  Photochemistry of ketocyanin dye ? polyenic bis-?,??-amino ketones substituted in the polyene chain

  摘要：

  The photochemistry of ketocyanin dyes, 15 polyenic bis-omega,omega'-amino ketones (PBAK), was studied by the methods of pulsed and laser photolysis. During the photoexcitation of the PBAK solutions, the formation of their cis-photoisomers is observed, whose relaxation kinetics into the initial trans-isomers is dependent on the intensity of the probing light. The energy of activation of the cis --> trans-isomerization process in the dark increases with decrease in the polarity of the solvent. During the photoexcitation of fluorine-substituted PBAK with a six-membered central ring, their cyclization takes place with the formation of pyran forms (PF) absorbing in the UV region; the PF then convert into the initial dye. The formation of PF partially proceeds via the intermediate formation of a cis-isomer of the dye. During the photoexcitation of deoxygenated solutions of PBK, the formation of their triplet states is also observed; the decay kinetics of the triplet states becomes accelerated with decrease in the solvating power of the solvent. This is explained by the decrease in the T-S0 splitting due to increase in the energy barrier of the cis-trans isomerization process. A scheme has been proposed for the potential surfaces of PBAK to explain this phenomenon. For some PBAK, the formation is observed of cis-photoisomers not only from the S1, but also from the T-state.

  DOI：

  10.1007/bf00957840
• 作为产物：
  描述：

  {8-[(E)-3-Dimethylamino-prop-2-en-(E)-ylidene]-3-fluoro-6,7,8,8a-tetrahydro-5H-chromen-2-yl}-dimethyl-amine 以 异丙醇 为溶剂， 生成 (2E,6E)-2-[(Z)-3-(dimethylamino)-2-fluoroprop-2-enylidene]-6-[(E)-3-(dimethylamino)prop-2-enylidene]cyclohexan-1-one
  参考文献：
  名称：

  Photochemistry of ketocyanin dye ? polyenic bis-?,??-amino ketones substituted in the polyene chain

  摘要：

  The photochemistry of ketocyanin dyes, 15 polyenic bis-omega,omega'-amino ketones (PBAK), was studied by the methods of pulsed and laser photolysis. During the photoexcitation of the PBAK solutions, the formation of their cis-photoisomers is observed, whose relaxation kinetics into the initial trans-isomers is dependent on the intensity of the probing light. The energy of activation of the cis --> trans-isomerization process in the dark increases with decrease in the polarity of the solvent. During the photoexcitation of fluorine-substituted PBAK with a six-membered central ring, their cyclization takes place with the formation of pyran forms (PF) absorbing in the UV region; the PF then convert into the initial dye. The formation of PF partially proceeds via the intermediate formation of a cis-isomer of the dye. During the photoexcitation of deoxygenated solutions of PBK, the formation of their triplet states is also observed; the decay kinetics of the triplet states becomes accelerated with decrease in the solvating power of the solvent. This is explained by the decrease in the T-S0 splitting due to increase in the energy barrier of the cis-trans isomerization process. A scheme has been proposed for the potential surfaces of PBAK to explain this phenomenon. For some PBAK, the formation is observed of cis-photoisomers not only from the S1, but also from the T-state.

  DOI：

  10.1007/bf00957840

文献信息

• Synthesis of dyes containing fluorine atoms in the polymethine chain
  作者：Zh. A. Krasnaya、T. S. Stytsenko、V. S. Bogdanov、N. V. Monich、M. M. Kul'chitskii、S. V. Pazenok、L. M. Yagupol'skii

  DOI：10.1007/bf00958049

  日期：1989.3