1,3,3-trimethyl-5-nitrospiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine] | 128171-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1,3,3-trimethyl-5-nitrospiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]
• 英文别名: 1-methyl-5-nitrospiro(indoline-2,3'-naphthoxazine)；1',3',3'-Trimethyl-5'-nitrospiro[benzo[f][1,4]benzoxazine-3,2'-indole]
• CAS: 128171-73-3
• 化学式: C₂₂H₁₉N₃O₃
• 分子量: 373.411
• InChiKey: UQSKYJFCTIZVKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3,3-trimethyl-5-nitrospiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine] 以 甲苯 为溶剂， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Gautron, Rene; Eloy, Dominique; Escaffre, Pascale, Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 4, p. 315 - 328

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 sodium nitrate 、 硫酸 、 三乙胺 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 15.0h， 生成 1,3,3-trimethyl-5-nitrospiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]
  参考文献：
  名称：

  Pottier, E.; Sergent, M.; Luu, R. Phan Tan, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 8, p. 719 - 740

  摘要：

  DOI：

文献信息

• Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
  作者：Edward I. Balmond、Brandon K. Tautges、Andrea L. Faulkner、Victor W. Or、Blanka M. Hodur、Jared T. Shaw、Angelique Y. Louie

  DOI：10.1021/acs.joc.6b01193

  日期：2016.10.7

  have the greatest effect on C–O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends

  螺吡喃和螺恶嗪代表一类重要的光致变色化合物，具有广泛的应用。为了有效地利用和设计这些光开关，需要了解取代基如何影响光致变色特性，以及在相同条件下如何比较不同的结构基序。在这项工作中，合成了一个小的光电开关库，以比较评估取代基修饰和结构对光致变色的影响。该文库旨在修饰据认为对C-O键不稳定性以及因此对光致变色性质影响最大的位置。本文中，我们报告了30种螺吡喃，螺吲哚并萘并螺恶嗪的紫外线和可见光响应的比较分析。还研究了ado（III）结合对化合物库的影响，以确定其对光开关的影响。两种测定均显示出取代基和最佳光致变色结构要求的不同趋势。
• Photochromism and solvatochromism of push–pull or pull–push spiroindolinenaphthoxazines
  作者：A. V. Metelitsa、V. Lokshin、J. C. Micheau、A. Samat、R. Guglielmetti、V. I. Minkin

  DOI：10.1039/b204603b

  日期：——

  The photochromic and solvatochromic behaviour of 17 variously substituted spiroindoline naphthoxazines has been investigated in cyclohexane, toluene, acetonitrile and methanol in fluid solution. Specific parameters such as the wavelengths and the molar absorption coefficients of the closed spiro- and open merocyanine forms, together with the photocoloration and photobleaching quantum yields, rate constants and activation energies of thermal fading have been determined under continuous monochromatic irradiation. It has been shown that most of these parameters are closely related to the electron distribution on the highly conjugated photomerocyanines and on their quinoidal or zwitterionic character. Depending on the acceptor or donor properties and on the position of their substituents, three classes of compounds have been detected.

  研究了 17 种不同取代形式的螺吲哚啉萘噁嗪在环己烷、甲苯、乙腈和甲醇的流体溶液中的光致变色和溶致变色行为。在连续单色辐照条件下，确定了封闭螺吲哚菁和开放美拉德菁形式的波长和摩尔吸收系数等具体参数，以及光变色和光漂白量子产率、热褪色速率常数和活化能。结果表明，这些参数大多与高度共轭的光致花青素上的电子分布以及它们的类醌或齐聚物特性密切相关。根据受体或供体的特性及其取代基的位置，可以检测到三类化合物。
• Eloy, D.; Escaffre, P.; Gautron, R., Journal de Chimie Physique et de Physico-Chimie Biologique, 1992, vol. 89, # 4, p. 897 - 914
  作者：Eloy, D.、Escaffre, P.、Gautron, R.、Jardon, P.

  DOI：——

  日期：——
• Microwave-Assisted Solvent-Free Synthesis of the Substituted Spiroindolinonaphth[2,1-b][1,4]oxazines
  作者：A. V. Koshkin、O. A. Fedorova、V. Lokshin、R. Guglielmetti、J. Hamelin、F. Texier-Boullet、S. P. Gromov

  DOI：10.1081/scc-120027269

  日期：2004.1

  The synthesis of the substituted spiroindolinonaphth[2,1-b][1,4]oxazines 3a-e is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-nitroso-2-naphthol under microwave irradiation. In the same conditions, in presence of morpholine the 6'-morpholinosubstituted compounds 4a, b, d, e are formed. The main advantages of the method are the short reaction time, solvent-free reaction condition, cleaner reaction products and the higher product yields in comparison with known methods of synthesis.
• Structures and photochromic properties of substituted spiroindolinonaphthoxazines
  作者：S. M. Aldoshin、I. I. Chuev、O. S. Filipenko、A. N. Utenyshev、V. Lokshin、P. Laregenie、A. Samat、R. Guglielmetti

  DOI：10.1007/bf02503477

  日期：1998.6

  Six indolinospironaphthoxazines were studied by X-ray diffraction analysis. demonstrated that the electronic nature of the substituents in the naphthoxazine and indoline fragments has no substantial effect on the C-spiro-O and C-spiro-N bond lengths. Photocolorability of the compounds under study depends only slightly on the above-mentioned bond lengths and correlates mainly with the energy of steric strain of the oxazine ring. The stability of the open forms of spiroindolinonaphthoxazines that formed upon photoirradiation is determined to a large extent by the electronic and steric nature of the substituents. The exception is the compound that contains the NO2 group in the indoline fragment. In the last-mentioned case, the cleavage of the ring occurs through a substantially different pathway.