5-methoxy-1,3,3-trimethyl-1,3-dihydrospiro<2H-indole-2,2'-<2H>-bipyrido<3,2-f><2,3-h><1,4>benzoxazine> | 151329-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 5-methoxy-1,3,3-trimethyl-1,3-dihydrospiro<2H-indole-2,2'-<2H>-bipyrido<3,2-f><2,3-h><1,4>benzoxazine>
• 英文别名: 5-methoxy-1,3,3-trimethylspiro[indole-2,2'-[2H]bipyrido[3,2-f][2,3-h][1,4]benzoxazine]；5-methoxy-1,3,3-trimethyl-1,3-dihydrospiro(2H-indole-2,2'-[2H]-bipyrido[3,2-f][2,3-h][1,4]benzoxazine)；5'-Methoxy-1',3',3'-trimethylspiro[[1,4]oxazino[2,3-f][1,10]phenanthroline-2,2'-indole]
• CAS: 151329-45-2
• 化学式: C₂₅H₂₂N₄O₂
• 分子量: 410.475
• InChiKey: KLUDJKAUBKRYFF-UHFFFAOYSA-N

物化性质

• 沸点：
  669.8±55.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methoxy-1,3,3-trimethyl-1,3-dihydrospiro<2H-indole-2,2'-<2H>-bipyrido<3,2-f><2,3-h><1,4>benzoxazine> 以 甲苯 为溶剂， 生成 6-[(Z)-5-Methoxy-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-6H-[1,10]phenanthrolin-5-one
  参考文献：
  名称：

  Solvatochromic and photochromic characteristics of new 1,3-dihydrospiro[2H-indole-2,2′-[2H]-bipyrido[3,2-f][2,3-h][1,4]benzoxazines]

  摘要：

  The mono-oxime of 1,10-phenanthroline-5,6-quinone reacts with 1,3,3-trimethyl-2-methyleneindoline derivatives to give the corresponding spirooxazines, i.e. 1,3-dihydrospiro[2H-indole-2,2'-[2H]-bipyrido[3,2-f][2,3-h][1,4)benzoxazines]. These compounds exhibit particular solvatochromic behaviour, strongly dependent on the substitution pattern. At room temperature and without any light excitation, an equilibrium is established between closed and opened forms. The photochromic characteristics have been determined using flash photolysis coupled to a fast scanning spectrometer allowing the determination of rate constants for thermal bleaching, visible absorption and photocoloration. The coloured opened forms, either photoinduced or arising from the solvation effect, appear to be spectroscopically identical. Structural parameters of the short-lived photomerocyanines have also been obtained.

  DOI：

  10.1039/p29930001327
• 作为产物：
  描述：

  5-methoxy-1,10-phenanthroline 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 5.5h， 生成 5-methoxy-1,3,3-trimethyl-1,3-dihydrospiro<2H-indole-2,2'-<2H>-bipyrido<3,2-f><2,3-h><1,4>benzoxazine>
  参考文献：
  名称：

  Solvatochromic and photochromic characteristics of new 1,3-dihydrospiro[2H-indole-2,2′-[2H]-bipyrido[3,2-f][2,3-h][1,4]benzoxazines]

  摘要：

  The mono-oxime of 1,10-phenanthroline-5,6-quinone reacts with 1,3,3-trimethyl-2-methyleneindoline derivatives to give the corresponding spirooxazines, i.e. 1,3-dihydrospiro[2H-indole-2,2'-[2H]-bipyrido[3,2-f][2,3-h][1,4)benzoxazines]. These compounds exhibit particular solvatochromic behaviour, strongly dependent on the substitution pattern. At room temperature and without any light excitation, an equilibrium is established between closed and opened forms. The photochromic characteristics have been determined using flash photolysis coupled to a fast scanning spectrometer allowing the determination of rate constants for thermal bleaching, visible absorption and photocoloration. The coloured opened forms, either photoinduced or arising from the solvation effect, appear to be spectroscopically identical. Structural parameters of the short-lived photomerocyanines have also been obtained.

  DOI：

  10.1039/p29930001327

文献信息

• Solvation effects on spirooxazine to merocyanine thermal reversion kinetics in acetonitrile-water binary mixtures
  作者：Elena B. Gaeva、V. Pimienta、A. V. Metelitsa、N. A. Voloshin、V. I. Minkin、J. C. Micheau

  DOI：10.1002/poc.847

  日期：2005.4

  irradiation is switched off, a slow thermal reversion of the closed spirooxazine to the open merocyanine takes place until the initial equilibrium position is reached. Kinetic analysis of a whole set of relaxation curves recorded at various water contents was used to establish a model involving multiple equilibria between three merocyanines in different solvation states (solvated by acetonitrile, solvated

  在溶液中，光致变色分子5-甲氧基螺并[吲哚-菲咯啉恶嗪]（SPO）及其相应的花菁开口异构体处于平衡状态。在纯乙腈中，大约有22.5％的开放形式，而在乙腈-水二元溶剂中，当水的摩尔分数χ（H 2O）约为0.80。在可见光范围内的照射导致光漂白的稳态，其中花菁开放异构体的比例显着降低。当关闭辐照时，封闭的螺恶嗪缓慢地热转化为开放的花菁，直至达到初始平衡位置。对在不同含水量下记录的整套弛豫曲线进行动力学分析，以建立一个模型，该模型涉及处于不同溶剂化状态（由乙腈溶解，由乙腈-水络合物溶解并水合）的三个部花菁之间的多重平衡。除了其相应的可见光谱外，还确定了它们的相对比例，该比例取决于二元混合物的组成。版权所有©2004 John Wiley＆Sons，Ltd.
• Solvatochromic and photochromic characteristics of new 1,3-dihydrospiro[2H-indole-2,2′-[2H]-bipyrido[3,2-f][2,3-h][1,4]benzoxazines]
  作者：Jean-Luc Pozzo、André Samat、Robert Guglielmetti、Denis De Keukeleire

  DOI：10.1039/p29930001327

  日期：——

  The mono-oxime of 1,10-phenanthroline-5,6-quinone reacts with 1,3,3-trimethyl-2-methyleneindoline derivatives to give the corresponding spirooxazines, i.e. 1,3-dihydrospiro[2H-indole-2,2'-[2H]-bipyrido[3,2-f][2,3-h][1,4)benzoxazines]. These compounds exhibit particular solvatochromic behaviour, strongly dependent on the substitution pattern. At room temperature and without any light excitation, an equilibrium is established between closed and opened forms. The photochromic characteristics have been determined using flash photolysis coupled to a fast scanning spectrometer allowing the determination of rate constants for thermal bleaching, visible absorption and photocoloration. The coloured opened forms, either photoinduced or arising from the solvation effect, appear to be spectroscopically identical. Structural parameters of the short-lived photomerocyanines have also been obtained.