1,3,3-trimethyl-5'-hydroxy-3'H-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]naphthoxazine | 132036-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3,3-trimethyl-5'-hydroxy-3'H-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]naphthoxazine
• 英文别名: 1,3,3-trimethyl-5'-hydroxyspiro-(indoline-2,3'-[3H]naphth[2,1-b][1,4]oxazine)；1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazin]-5'-ol；5'-hydroxy-1,3,3-trimethylspiroindolinonaphthooxazine；1',3',3'-Trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]-5-ol
• CAS: 132036-04-5
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: PRZBBEQYTHELGL-UHFFFAOYSA-N

物化性质

• 沸点：
  576.4±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 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：
  45.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3,3-trimethyl-5'-hydroxy-3'H-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]naphthoxazine 以 甲苯 为溶剂， 生成 3-Hydroxy-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one
  参考文献：
  名称：

  Structure-visible absorption relationship in the photochromic spiro[indoline-naphthoxazine] series

  摘要：

  DOI：

  10.1002/(sici)1099-1395(199605)9:5<262::aid-poc781>3.0.co;2-a
• 作为产物：
  描述：

  3-Hydroxy-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one 以 环己烷 为溶剂， 生成 1,3,3-trimethyl-5'-hydroxy-3'H-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]naphthoxazine
  参考文献：
  名称：

  Photochromism and solvatochromism of push–pull or pull–push spiroindolinenaphthoxazines

  摘要：

  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。

  DOI：

  10.1039/b204603b

文献信息

• Crown-containing spirooxazines and spiropyrans
  作者：O. A. Fedorova、S. P. Gromov、Yu. P. Strokach、Yu. V. Pershina、S. A. Sergeev、V. A. Barachevskii、G. Pepe、A. Samat、R. Guglielmetti、M. A. Alfimov

  DOI：10.1007/bf02494754

  日期：1999.10

  Methods for the synthesis of new spironaphthooxazines containing an aza-15-crown-5 fragment in two different positions (5′ and 9′) were developed. The spectral and photochemical properties of these compounds suggest that two competitive complexation processes occur with alkaline-earth or rare-earth metal cations differing in efficiency and selectivity. A metal cation occupies the optimum position in

  开发了在两个不同位置（5' 和 9'）包含 aza-15-crown-5 片段的新型螺萘并恶嗪的合成方法。这些化合物的光谱和光化学性质表明，两种竞争性络合过程与碱土金属或稀土金属阳离子的效率和选择性不同。金属阳离子相对于染料的部花青形式的供体氧原子占据冠醚腔中的最佳位置，因此与分子间相互作用的情况相比，可以更强烈地影响其光谱和光化学性质。
• Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst
  作者：Shailesh N. Vajekar、Ganapati S. Shankarling

  DOI：10.1080/00397911.2019.1694690

  日期：2020.2.1

  Abstract A greener route for the synthesis of the photochromic spironaphthoxazines employing a highly efficient, biodegradable and recyclable choline hydroxide catalyst in an aqueous medium has been described. This methodology offers diverse advantages such as mild reaction conditions, short reaction time (1 h), excellent yields (up to 91%), and operational simplicity that make it a useful and attractive

  摘要描述了一种在水性介质中使用高效、可生物降解和可回收的氢氧化胆碱催化剂合成光致变色螺萘恶嗪的绿色途径。该方法具有多种优势，例如反应条件温和、反应时间短（1 小时）、优异的产率（高达 91%）和操作简单，使其成为合成螺萘恶嗪的有用且有吸引力的选择。氢氧化胆碱显示出优异的催化性能，直至五次循环均未显着降低活性。通过1H NMR谱和熔点推断合成的螺萘恶嗪的结构。图形概要
• Fedorova, Olga A.; Gromov, Sergey P.; Pershina, Yulia V., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 3, p. 563 - 570
  作者：Fedorova, Olga A.、Gromov, Sergey P.、Pershina, Yulia V.、Sergeev, Sergey S.、Strokach, Yuri P.、Barachevsky, Valeri A.、Alfimov, Michael V.、Pepe, Gerard、Samat, Andre、Guglielmetti, Robert

  DOI：——

  日期：——
• The molecular design, synthesis and photochromic properties of spirooxazines containing a permanent azo (hydrazone) chromophore
  作者：Robert M. Christie、Keith M. Morgan、Ayesha Rasheed、Mohanad Aldib、Georgina Rosair

  DOI：10.1016/j.dyepig.2013.02.017

  日期：2013.8

  A range of molecular modelling techniques has been applied to predict optimized geometrical conformations and energies of the ring-closed oxazine form and ring-opened merocyanine forms of three azospirooxazines. A comparison of the relative stabilities of the possible isomers of the merocyanines was carried out by applying molecular mechanics (augmented MM2), while the prediction of the potential for photochromic behaviour was made by comparison of the heats of formation calculated by AMI. Synthetic routes were explored and as a result two azospirooxazines were isolated, one of which showed interesting and unusual photochromic behaviour. The instability of this compound towards purification by chromatography was investigated. The decomposition product was isolated and characterized with the aid of single crystal x-ray crystallography. The correlation between predicted and observed photochromic behaviour is discussed. (C) 2013 Elsevier Ltd. All rights reserved.
• Thermally activated and light-induced metal ion complexation of 5′-(hydroxy)spiroindolinonaphthooxazines in polar solvents
  作者：Stela Minkovska、Monika Fedieva、Bojana Jeliazkova、Todor Deligeorgiev

  DOI：10.1016/j.poly.2004.09.022

  日期：2004.12

  Chelation with Al(III), Fe(II) or Cu(II) of the open photomerocyanine form obtained under steady irradiation of spiroindolinonaphthooxazines, with a hydroxyl group at the 5' position in the naphthooxazine moiety, induces a slight hypsochromic shift of its visible absorption band and increases the lifetime of this form, slowing down its thermal bleaching in the dark (rate constant similar to10(-3) s(-1)). Complexation with Al(III), Fe(II) or Cu(II) allows the spiroindolinonaphthooxazines to isomerize to their open coloured form even under dark conditions giving a complex spectroscopically identical to the photoinduced product. The activation energy of thermal complexation is independent of the metal ion which implies the ring opening as the rate determining step. (C) 2004 Elsevier Ltd. All rights reserved.