5-nitro-1,2,3,3-tetramethyl-3H-indol-1-ium perchlorate | 86879-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-nitro-1,2,3,3-tetramethyl-3H-indol-1-ium perchlorate
• 英文别名: 1,2,3,3-tetramethyl-5-nitro-3H-indolium perchlorate；1,2,3,3-Tetramethyl-5-nitro-3H-indol-1-ium perchlorate；1,2,3,3-tetramethyl-5-nitroindol-1-ium;perchlorate
• CAS: 86879-79-0
• 化学式: C₁₂H₁₅N₂O₂*ClO₄
• 分子量: 318.714
• InChiKey: ULRTYAWPBVKSAZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.14
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-formylthiochromone 、 5-nitro-1,2,3,3-tetramethyl-3H-indol-1-ium perchlorate 以 乙醇 为溶剂， 以71%的产率得到1,3,3-trimethyl-5-nitro-2-(4-oxo-4H-1-benzothiopyran-3-ylethenyl)indolium perchlorate
  参考文献：
  名称：

  Photochromic properties of cationic merocyanine dyes. Thermal stability of the spiropyran form produced by irradiation with visible light

  摘要：

  通过缩合反应制备了一系列新型阳离子型部花青染料，该反应涉及1,2,3,3-四甲基吲哚鎓衍生物与3-醛基-4H-1-苯并噻吡喃或苯并吡喃衍生物的反应，并研究了它们的光致变色性质，特别关注吲哚鎓部分中的取代基效应。这些染料在可见光照射下转化为无色的螺吡喃（SP）形式，尽管在黑暗环境中，带色的部花青（MC）形式会再次出现。热致变色受到两个因素的影响：吲哚鎓部分的取代基和反荷离子。在5位带有供电子取代基（如甲氧基）有效地延缓了热致变色，而吸电子基团（如硝基）则加速了热致变色。这些取代基效应提供了良好的Hammett规则线性关系，对应于para σ参数，表明在SP形式中吲哚部分电子密度降低促进了螺碳与吡喃环氧之间键的异裂解离。

  DOI：

  10.1039/a905098a

文献信息

• Synthesis and structure of indoline spiropyrans based on benzo[f]coumarin
  作者：O. G. Nikolaeva、O. Yu. Karlutova、A. A. Guseva、E. B. Gaeva、A. G. Starikov、A. D. Dubonosov、V. A. Bren、A. V. Metelitsa、V. I. Minkin

  DOI：10.1007/s11172-020-2912-6

  日期：2020.7

  Indoline spiropyrans containing benzo[f]coumarin moiety annulated to the 2H-pyran cycle were synthesized. The obtained compounds exist in solutions as a tautomeric mixture of their spirocyclic and merocyanine forms. The spiro form exhibits an enhanced resistance to UV irradiation and does not rearranges into the merocyanine isomer in the temperature range of 278–303 K.

  合成了含有与 2H-吡喃循环成环的苯并[f]香豆素部分的二氢吲哚螺吡喃。所得化合物以其螺环和部花青形式的互变异构混合物存在于溶液中。螺形式对紫外线照射具有增强的抵抗力，并且在 278-303 K 的温度范围内不会重新排列成部花青异构体。
• Synthesis and studies of new photochromic spiropyrans containing a formylcoumarin fragment
  作者：O. G. Nikolaeva、A. V. Metelitsa、A. S. Cheprasov、O. Yu. Karlutova、A. G. Starikov、A. D. Dubonosov、V. A. Bren´、V. I. Minkin

  DOI：10.1007/s11172-016-1396-x

  日期：2016.4

  A computer search for new photoactive compounds among indoline spiropyrans of coumarin series was carried out using DFT B3LYP/6-31G(d,p) method. Based on the data obtained, the spiropyrans containing a formylcoumarin fragment annulated to the 2H-pyran ring and possessing photochromic properties were synthesized. The structure and photochromism of these compounds were studied by 1H NMR, IR, and UV/Vis

  使用 DFT B3LYP/6-31G(d,p) 方法在香豆素系列二氢吲哚螺吡喃中寻找新的光活性化合物。根据获得的数据，合成了含有与 2H-吡喃环成环的甲酰香豆素片段并具有光致变色特性的螺吡喃。通过1H NMR、IR和UV/Vis光谱研究了这些化合物的结构和光致变色。将甲酰基引入螺吡喃的香豆素部分导致部花青异构体的长波长吸收最大值发生红移，并显着延长其寿命。
• Novel photochromic indolinospiropyrans of coumarin series with high level of colorability
  作者：Anatoly V. Metelitsa、Olga G. Nikolaeva、Alexander S. Cheprasov、Olga Yu. Karlutova、Anastasia A. Burtseva、Alexander D. Dubonosov、Vladimir A. Bren、Vladimir I. Minkin

  DOI：10.1016/j.jphotochem.2016.01.019

  日期：2016.5

  Indolinospiropyrans containing coumarin moiety annulated to the 2H-pyran ring at the 6,5-position exhibit positive photochromism under normal conditions and are characterized by exceptionally high values of colorability. Both strong electron donating and electron withdrawing 5-R substituents in the indoline moiety provide for the noticeable decrease of colorability. Negative solvatochromism of merocyanine

  在正常条件下，含有在6,5-位环成2 H-吡喃环的香豆素部分的吲哚螺并吡喃并显示出正的光致变色现象，并且其着色力值极高。二氢吲哚部分中的强供电子和吸电子5-R取代基都显着降低了可着色性。合成的螺吡喃的花菁异构体的负溶剂溶变现象表明其偶极结构，这通过增加溶剂极性时再循环速率常数的降低来体现。
• Novel merocyanine dyes are converted into the spiropyran form by irradiation with visible light
  作者：Hiroyuki Nakazumi、Katsumi Maeda、Shigeyuki Yagi、Teijiro Kitao

  DOI：10.1039/c39920001188

  日期：——

  New photochromic spiropyrans existing in a stable coloured form are prepared from merocyanine dyes by irradiation with visible light.

  以稳定的有色形式存在的新型光致变色螺吡喃是由部花青染料通过可见光照射制备的。
• Synthesis and photochromic properties of spiropyrans containing a fused benzopyranone fragment
  作者：O. G. Nikolaeva、E. B. Gaeva、E. N. Shepelenko、A. V. Tsukanov、A. V. Metelitsa、B. S. Luk’yanov、A. D. Dubonosov、V. A. Bren’、V. I. Minkin

  DOI：10.1134/s1070428009070173

  日期：2009.7

  New spiro compounds of the indole, phthalazine, isobenzofuran, and benzopyran series, containing a fused benzopyranone fragment in the chromene moiety, were synthesized. Indole derivatives were found to exhibit photochromic properties under stationary conditions at 293 K. The thermal stability of merocyanine isomers sharply decreases upon introduction of electron-withdrawing nitro group into the indole fragment and fusion of a benzene ring to the chromene fragment.