1,3,3-trimethyl-9'-hydroxyspiro[indoline-2,3'-[3H]naphtho[2,1-b](1,4)oxazine] | 104989-11-9

• 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-9'-hydroxyspiro[indoline-2,3'-[3H]naphtho[2,1-b](1,4)oxazine]
• 英文别名: 1,3,3-trimethyl-9'-hydroxy-3'H-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]；9'-hydroxy-1,3,3-trimethylspiroindolinonaphthooxazine；9'-hydroxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine]；9'-hydroxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtha[2,1-b][1,4]oxazine]；3',3'-dimethyl-1'-methylspiro(2H-naphtho[2,1-b]-1,4-oxazine-2,2'-indoline)；1,3,3-trimethyl-9'-hydroxy-3'H-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]naphthoxazine；1,3,3-trimethylspiro[indolin-2,3'[3H]-naphtho[2,1-b][1,4]oxazin]-9'-ol；1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazin]-9'-ol；1,3,3-trimethyl-9′-hydroxy-spiroindolinenaphthoxazine；1,3,3-trimethyl-9'-hydroxy-spiroindolinenaphthoxazine；9'-hydroxy-1,3,3-trimethyl-1,3-dihydrospiro[2H-indole-2,3'-3'H-naphtho[2,1-b][1,4]-oxazine]；1,3,3-trimethylspiro[indoline-2,3′-naphtho-[2,1-b][1,4]oxazin]-9′-ol；9'-hydroxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphth[2,1-b][1,4]oxazine]；1,3,3-trimethyl-9'-hydroxyspiro[indoline-2,3-naphtho[2,1-b][1,4]oxazine]；1,3,3-trimethyl-9'-hydroxyspiro[indoline-2,3'-[3H]-naphtho[2,1-b] (1,4)oxazine]；1',3',3'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]-9-ol
• CAS: 104989-11-9
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: IPGFMOWJULBATG-UHFFFAOYSA-N

物化性质

• 熔点：
  211.5-214 °C
• 沸点：
  579.1±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-9'-hydroxyspiro[indoline-2,3'-[3H]naphtho[2,1-b](1,4)oxazine] 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Photoswitching electrospun nanofiber based on a spironaphthoxazine–isophorone-based fluorescent dye system

  摘要：

  A bistable photoswitching photochromic spironaphthoxazine/isophorone-based fluorescent dye system was investigated. The photoregulated fluorescence switching behavior of a spironaphthoxazine/isophorone dye loaded poly(methyl methacrylate) nanofiber was also studied. Reversible modulation of fluorescence intensity was achieved using alternating irradiation with UV and visible light. The erasable and rewritable optical storage based on spironaphthoxazine/isophorone dye loaded poly(methyl methacrylate) nanofiber has been developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.06.002
• 作为产物：
  描述：

  2,7-二羟基萘 在 硫酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1,3,3-trimethyl-9'-hydroxyspiro[indoline-2,3'-[3H]naphtho[2,1-b](1,4)oxazine]
  参考文献：
  名称：

  双重光响应和pH响应的螺恶嗪功能化的葡聚糖纳米颗粒。

  摘要：

  通过用螺恶嗪衍生物（SO-COOH）对葡聚糖进行官能化，合成了对光和pH有响应的螺恶嗪功能化的聚合物。官能化的葡聚糖衍生物可以在水性介质中形成纳米颗粒。在紫外光照射下，螺恶嗪官能化的葡聚糖（Dex-SO）纳米颗粒异构化为两性离子型花菁官能化的葡聚糖（Dex-MC），这导致聚集。但是，该过程在可见光照射下是可逆的。在酸性条件下，疏水的螺恶嗪质子化，并且纳米颗粒分别在5或3的pH值下聚集或溶胀。疏水荧光染料尼罗红作为模型药物的包封使我们可以获得有关在紫外线和酸处理的刺激下结构变化的更多信息。

  DOI：

  10.1021/acs.biomac.0c00642

文献信息

• Thermo- and Acid-Responsive Photochromic Spironaphthoxazine-Containing Organogelators
  作者：Yongguang Li、Keith Man-Chung Wong、Anthony Yiu-Yan Tam、Lixin Wu、Vivian Wing-Wah Yam

  DOI：10.1002/chem.201000150

  日期：2010.8.2

  A series of photochromic spironaphthoxazine derivatives has been designed, synthesized, and characterized by using 1H NMR spectroscopy, FAB mass spectrometry, and elemental analysis. Their photophysical and photochromic behavior have been investigated. Two of the compounds (G12‐en‐SA‐SO and G16‐en‐SA‐SO) have been shown to be capable of forming stable thermoreversible organogels in organic solvents

  通过使用1 H NMR光谱，FAB质谱和元素分析，设计，合成和表征了一系列光致变色螺萘并恶嗪衍生物。已经研究了它们的光物理和光致变色行为。两种化合物（G 12 -en-SA-SO和G 16 -en-SA-SO）已证明能够在有机溶剂中形成稳定的热可逆有机凝胶，并通过“稳定转化试验”进行了测试。管”方法。p-的加法发现甲苯磺酸在低于临界胶凝浓度（cgc）的浓度下诱导形成稳定的有机凝胶，并伴随着颜色从无色到紫色的变化。干凝胶的透射电子显微镜和扫描电子显微镜在微米级显示出典型的纤维结构。通过在各种温度下的动力学研究，已确定了乙醇中的G 8 en-SA-SO和凝胶态的G 16 en-SA-SO的漂白反应的活化参数。结果表明，凝胶态的漂白反应速率比溶液态的漂白反应速率慢得多。
• 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。
• Synthesis, Characterization and Photochromic Studies of Spirooxazine-Containing 2,2′-Bipyridine Ligands and Their Rhenium(i) Tricarbonyl Complexes
  作者：Chi-Chiu Ko、Li-Xin Wu、Keith Man-Chung Wong、Nianyong Zhu、Vivian Wing-Wah Yam

  DOI：10.1002/chem.200305485

  日期：2004.2.6

  of spirooxazine-containing 2,2'-bipyridine ligands and their rhenium(i) tricarbonyl complexes has been designed and synthesized, and their photophysical, photochromic and electrochemical properties have been studied. The X-ray crystal structures of two of the complexes have been determined. Detailed studies showed that the emission properties of the complexes could readily be switched through photochromic

  设计并合成了一系列含螺恶嗪的2,2'-联吡啶配体及其（（i）三羰基配合物，并对其光物理，光致变色和电化学性质进行了研究。已经确定了两个配合物的X射线晶体结构。详细的研究表明，通过光致变色反应可以很容易地改变配合物的发射性质。
• Regioselective ortho-formylation of hydroxy-substituted spironaphthooxazine
  作者：N. L. Zaichenko、L. S. Kol’tsova、I. M. Shcherbakova、O. Yu. Os’kina、V. N. Voznesenskii、I. R. Mardaleishvili、A. I. Shienok

  DOI：10.1007/s11172-011-0083-1

  日期：2011.3

  Formylation of photochromic 9′-hydroxy-1,3,3-trimethyl-1,3-dihydrospiro[2H-indole-2,3′-3′H-naphtho[2,1-b][1,4]oxazine] with the paraformaldehyde-MgCl2-Et3N system or by the Reimer-Tiemann reaction proceeds at the ortho-position to the hydroxy group to form 10′-formyl derivative.

  用乙醇铝和氯化镁的体系或通过Reimer-Tiemann反应对光变色的9′-羟基-1,3,3-三甲基-1,3-二氢螺[2H-吲哚-2,3′-3′H-萘[2,1-b][1,4]噁嗪]进行甲酰化反应，在羟基的邻位进行，形成10′-甲酰衍生物。
• Synthesis of Thiophene-Substituted Spiropyrans and Spirooxazines, Precursors of Photochromic Polymers
  作者：Corinne Moustrou、Andr� Samat、Robert Guglielmetti、Roger Dubest、Francis Garnier

  DOI：10.1002/hlca.19950780722

  日期：1995.11.1

  The synthesis of spiropyrans 11 and 12 and spirooxazines 13–17 containing a thiophene moiety is described. Two different synthetic approaches were used. The spectrokinetic properties of these new compounds are reported.

  描述了含有噻吩部分的螺吡喃11和12以及螺恶嗪13-17的合成。使用了两种不同的合成方法。报道了这些新化合物的光谱动力学性质。