5-amino-6,8-dimethylquinolin-4(1H)-one | 1401094-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-amino-6,8-dimethylquinolin-4(1H)-one
• 英文别名: 5-amino-6,8-dimethyl-1H-quinolin-4-one
• CAS: 1401094-95-8
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: XJQJHAISTZNJJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二叔丁基苯醌 、 5-amino-6,8-dimethylquinolin-4(1H)-one 以 丙醇 为溶剂， 以0.2407 g的产率得到5-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dienylideneamino)-6,8-dimethylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and Structural Investigation of an “Oxazinoquinolinespirohexadienone” That Only Exists as Its Long-Wavelength Ring-Opened Quinonimine Isomer

  摘要：

  The spirocyclic oxazinoquinolinespirohexadienone (OSHD) "photochromes" are computationally predicted to be an attractive target as electron deficient analogues of the perimidinespirohexadienone (PSHD) photochromes, for eventual application as photochromic photooxidants. We have found the literature method for their preparation unsuitable and present an alternative synthesis. Unfortunately the product of this synthesis is the long wavelength (LW) ring-opened quinonimine isomer of the OSHD. We have found this isomer does not close to the spirocyclic short wavelength isomer (SW) upon prolonged standing in the dark, unlike other PSHD photochromes. The structure of this long wavelength isomer was found by NMR and X-ray crystallography to be exclusively the quinolinone (keto) tautomer, though experimental cyclic voltammetry supported by our computational methodology indicates that the quinolinol (enol) tautomer (not detected by other means) may be accessible through a fast equilibrium lying far toward the keto tautomer. Computations also support the relative stability order of keto LW over enol LW over SW.

  DOI：

  10.1021/jo3016083
• 作为产物：
  描述：

  5-Amino-4-chloro-6,8-dimethylquinoline 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 22.0h， 以63%的产率得到5-amino-6,8-dimethylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and Structural Investigation of an “Oxazinoquinolinespirohexadienone” That Only Exists as Its Long-Wavelength Ring-Opened Quinonimine Isomer

  摘要：

  The spirocyclic oxazinoquinolinespirohexadienone (OSHD) "photochromes" are computationally predicted to be an attractive target as electron deficient analogues of the perimidinespirohexadienone (PSHD) photochromes, for eventual application as photochromic photooxidants. We have found the literature method for their preparation unsuitable and present an alternative synthesis. Unfortunately the product of this synthesis is the long wavelength (LW) ring-opened quinonimine isomer of the OSHD. We have found this isomer does not close to the spirocyclic short wavelength isomer (SW) upon prolonged standing in the dark, unlike other PSHD photochromes. The structure of this long wavelength isomer was found by NMR and X-ray crystallography to be exclusively the quinolinone (keto) tautomer, though experimental cyclic voltammetry supported by our computational methodology indicates that the quinolinol (enol) tautomer (not detected by other means) may be accessible through a fast equilibrium lying far toward the keto tautomer. Computations also support the relative stability order of keto LW over enol LW over SW.

  DOI：

  10.1021/jo3016083

文献信息

• Synthesis and Structural Investigation of an “Oxazinoquinolinespirohexadienone” That Only Exists as Its Long-Wavelength Ring-Opened Quinonimine Isomer
  作者：Benjamin J. Pollock、Christos A. Sikes、Ryan P. Ter Louw、Scott R. Hawken、Amy L. Speelman、Eugene J. Lynch、Daniel J. Stanford、Kraig A. Wheeler、Jason G. Gillmore

  DOI：10.1021/jo3016083

  日期：2012.10.5

  The spirocyclic oxazinoquinolinespirohexadienone (OSHD) "photochromes" are computationally predicted to be an attractive target as electron deficient analogues of the perimidinespirohexadienone (PSHD) photochromes, for eventual application as photochromic photooxidants. We have found the literature method for their preparation unsuitable and present an alternative synthesis. Unfortunately the product of this synthesis is the long wavelength (LW) ring-opened quinonimine isomer of the OSHD. We have found this isomer does not close to the spirocyclic short wavelength isomer (SW) upon prolonged standing in the dark, unlike other PSHD photochromes. The structure of this long wavelength isomer was found by NMR and X-ray crystallography to be exclusively the quinolinone (keto) tautomer, though experimental cyclic voltammetry supported by our computational methodology indicates that the quinolinol (enol) tautomer (not detected by other means) may be accessible through a fast equilibrium lying far toward the keto tautomer. Computations also support the relative stability order of keto LW over enol LW over SW.