5-bromo-2,3,3-trimethyl-1-propyl-3H-indol-1-ium iodide | 1387444-41-8

• 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-bromo-2,3,3-trimethyl-1-propyl-3H-indol-1-ium iodide
• CAS: 1387444-41-8
• 化学式: C₁₄H₁₉BrN*I
• 分子量: 408.12
• InChiKey: JAYBMNJFPNMLAD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.01
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  5-bromo-2,3,3-trimethyl-1-propyl-3H-indol-1-ium iodide 、 3-(1,3-benzoxazol-2-yl)-5-chloro-2-hydroxybenzaldehyde 在 三乙胺 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 5.0h， 以56%的产率得到8'-(1,3-benzoxazol-2-yl)-5-bromo-6'-chloro-3,3-dimethyl-1-propylspiro[indoline-2,2'-chromene]
  参考文献：
  名称：

  Photo- and thermochromic spiropyrans 43*. Spectral kinetic study of new benzoxazolyl-substituted spirobenzopyrans

  摘要：

  [GRAPHICS]A series of spiroindolinebenzopyrans was prepared, containing a chelating 1,3-benzoxazole group at position 8 of the benzopyran fragment. These new benzoxazolyl-substituted spirobenzopyrans showed photochromic properties in solutions with similar quantum yield values for the direct and reverse photoreactions.

  DOI：

  10.1007/s10593-015-1688-3
• 作为产物：
  描述：

  3-甲基-2-丁酮 在 硫酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 5-bromo-2,3,3-trimethyl-1-propyl-3H-indol-1-ium iodide
  参考文献：
  名称：

  微波辅助和环境友好的方法合成近红外荧光五甲胺花青染料

  摘要：

  开发了一种省时，环保的微波方法，并将其用于合成五甲胺花青染料及其相应前体的系统库。本文概述的合成从几天到几分钟极大地减少了五甲胺碳菁染料合成的反应途径，并且与常规加热方法（18-64％）相比，产率提高（89-98％）。通过微波辅助有机合成方法合成了十二个五次甲基花青染料实例，该化合物在快速的反应时间内提供了优异的收率，并使用简便的分离方法获得了该实例。此外，制备了三种具有新的亚甲基二氧基杂环结构的花青，与未取代的对应物相比，它们具有约40 nm的红移。

  DOI：

  10.1016/j.dyepig.2014.07.035

文献信息

• Benzothiazolyl substituted spiropyrans with ion-driven photochromic transformation
  作者：Anatoly V. Chernyshev、Nikolai A. Voloshin、Irina A. Rostovtseva、Oleg P. Demidov、Konstantin E. Shepelenko、Ekaterina V. Solov'eva、Elena B. Gaeva、Anatoly V. Metelitsa

  DOI：10.1016/j.dyepig.2020.108337

  日期：2020.7

  colored complexes. Composition, stability and spectroscopic characteristics of complexes have been investigated depending on the metal ion nature and substituents in ligand molecules. The colored complexes possess negative photochromism. The visible light irradiation causes their bleaching with quantum yields up to 48%. The benzothiazole substituted spiropyrans demonstrate ion driving photochromic transformation

  目前的工作致力于合成和详细研究新的含8-苯并噻唑的螺吡喃。被研究的螺吡喃存在于无色螺环异构体下，表现出正的光致变色，并伴有热和光诱导的逆反应。紫外线照射导致其有效着色，量子产率高达44％。可见光引起的反向光环化效率不超过0.1％。该特征将它们与先前研究的苯并恶唑类似物区分开。二氢吲哚片段取代基的吸电子性能的增强促进了光致着色效率的提高。取决于取代基，有色形式的寿命在17到200.8 s（丙酮，293 K）之间变化。由于存在苯并噻唑部分，花青素可以有效结合锌2+，Co 2 +，Ni 2 +，Cu 2 +，Cd 2 +，Mn 2+离子。将这些离子的盐添加到螺吡喃溶液中，可以使色彩鲜艳的络合物形式的花菁稳定。根据金属离子的性质和配体分子中的取代基，研究了配合物的组成，稳定性和光谱特性。有色配合物具有负光致变色作用。可见光照射导致其漂白，量子产率高达48％。苯并噻唑取代的螺吡喃证明了离子驱动的光致变色转化。
• Polychromogenic molecular systems based on photo- and ionochromic spiropyrans
  作者：Anatoly V. Chernyshev、Nikolai A. Voloshin、Irina A. Rostovtseva、Ekaterina V. Solov'eva、Elena B. Gaeva、Anatoly V. Metelitsa

  DOI：10.1016/j.dyepig.2018.05.040

  日期：2018.11

  bearing benzoxazole fragment in the position 8 of the benzopyran part appear as polychromogenic molecular systems exhibiting not only photochromic but also ionochromic properties. Photochromic properties demonstrate variability of spectral kinetic characteristics in the wide range depending on structural features and a solvent nature. Efficiency of photocoloration process is more than one order of

  所获得的螺并吲哚啉苯并吡喃在苯并吡喃部分的第8位带有苯并恶唑片段，表现为不仅具有光致变色性质而且具有离子致变色性质的多色分子体系。光致变色特性表明光谱动力学特性在很大范围内具有变化性，这取决于结构特征和溶剂性质。光致变色过程的效率比光致漂白量子产率高出一个数量级。由于存在苯并恶唑片段，其电致变色性质允许检测诸如Co 2 +，Ni 2 +，Zn 2 +，Cu 2 +，Cd 2+的金属阳离子的存在。以Ni 2 +，Zn 2+为例离子变色效应已被定量描述。将获得的螺吡喃中的光致变色和离子致变色相结合，提供了创建具有光驱动识别功能的金属离子化学传感器的机会。
• Photo- and thermochromic spirans. 35.* Synthesis and photochromic properties of spiro[indoline-2,3′-pyrano[3,2-f]quinolines] and their cationic derivatives
  作者：N. A. Voloshin、S. O. Bezuglyi、A. V. Metelitsa、E. V. Solov’eva、K. E. Shepelenko、V. I. Minkin

  DOI：10.1007/s10593-012-1025-z

  日期：2012.6

  New photochromic spiropyranoquinolines and their cationic derivatives have been synthesized. Quaternization of the quinoline fragment leads to significant enhancement of the thermal stability of the merocyanine isomers of these cationic spiropyrans.
• A Light‐Triggered J‐Aggregation‐Regulated Therapy Conversion: from Photodynamic/Photothermal Therapy to Long‐Lasting Chemodynamic Therapy for Effective Tumor Ablation
  作者：Kai Wei、Yanxin Wu、Xian Zheng、Li Ouyang、Guiping Ma、Chendong Ji、Meizhen Yin

  DOI：10.1002/anie.202404395

  日期：2024.6.3

  Reactive oxygen species (ROS) have become an effective tool for tumor treatment. The combination of photodynamic therapy (PDT) and chemodynamic therapy (CDT) takes advantage of various ROS and enhances therapeutic effects. However, the activation of CDT usually occurs before PDT, which hinders the sustained maintenance of hydroxyl radicals (⋅OH) and reduces the treatment efficiency. Herein, we present a light‐triggered nano‐system based on molecular aggregation regulation for converting cancer therapy from PDT/photothermal therapy (PTT) to a long‐lasting CDT. The ordered J‐aggregation enhances the photodynamic properties of the cyanine moiety while simultaneously suppressing the chemodynamic capabilities of the copper‐porphyrin moiety. Upon light irradiation, Cu‐PCy JNPs demonstrate strong photodynamic and photothermal effects. Meanwhile, light triggers a rapid degradation of the cyanine backbone, leading to the destruction of the J‐aggregation. As a result, a long‐lasting CDT is sequentially activated, and the sustained generation of ⋅OH is observed for up to 48 hours, causing potent cellular oxidative stress and apoptosis. Due to their excellent tumor accumulation, Cu‐PCy JNPs exhibit effective in vivo tumor ablation through the converting therapy. This work provides a new approach for effectively prolonging the chemodynamic activity in ROS‐based cancer therapy.