1-(3-hydroxypropyl)-2,3,3-trimethyl-3H-indolium iodide | 1218811-37-0

• 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: 1-(3-hydroxypropyl)-2,3,3-trimethyl-3H-indolium iodide
• 英文别名: 1-(3-hydroxypropyl)-2,3,3-trimethyl-3H-indol-1-ium iodide；3-(2,3,3-Trimethylindol-1-ium-1-yl)propan-1-ol;iodide
• CAS: 1218811-37-0
• 化学式: C₁₄H₂₀NO*I
• 分子量: 345.223
• InChiKey: WWYVRWNOTUBKQQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxypropyl)-2,3,3-trimethyl-3H-indolium iodide 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以43%的产率得到2,3,3-trimethylindolino(1,2-b)oxazine
  参考文献：
  名称：

  Synthesis of DNA with Spirobenzopyran as an Internal Covalent Modification

  摘要：

  通过两种不同的合成策略，光致变色螺吡喃被作为内部修饰引入到寡核苷酸中：第一条路线是将螺吡喃膦酰胺合成作为DNA构建模块，而第二条路线则采用了后合成“点击”型连接反应。在双链DNA中，色素的光诱导开环未能实现。

  DOI：

  10.1055/s-0029-1219924
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 、 3-碘丙醇 以 氯仿 为溶剂， 反应 24.0h， 以99%的产率得到1-(3-hydroxypropyl)-2,3,3-trimethyl-3H-indolium iodide
  参考文献：
  名称：

  Synthesis of DNA with Spirobenzopyran as an Internal Covalent Modification

  摘要：

  通过两种不同的合成策略，光致变色螺吡喃被作为内部修饰引入到寡核苷酸中：第一条路线是将螺吡喃膦酰胺合成作为DNA构建模块，而第二条路线则采用了后合成“点击”型连接反应。在双链DNA中，色素的光诱导开环未能实现。

  DOI：

  10.1055/s-0029-1219924

文献信息

• A photo-stable and reversible pH-responsive nano-agent based on the NIR phenazine dye for photoacoustic imaging-guided photothermal therapy
  作者：Yongchao Yan、Hao Fu、Jian Wang、Chuanrong Chen、Qi Wang、Yourong Duan、Jianli Hua

  DOI：10.1039/c9cc05624f

  日期：——

  A photo-stable and reversible pH-responsive phenazine dye displayed an obvious NIR absorption in a weak acid environment of tumor. The dye assembled into nanoparticles was developed for photoacoustic imaging-guided photothermal therapy in mice.

  一种光稳定、可逆pH响应的菲嗪染料，在肿瘤的弱酸环境中显示出明显的近红外吸收。该染料组装成纳米粒子，用于小鼠的光声成像引导下的光热治疗。
• 一种利用花菁衍生pH响应光功能分子抑制伤口细菌感染的微针贴片
  申请人：长春工业大学

  公开号：CN117924318A

  公开（公告）日：2024-04-26

  本发明所提出的一种利用花菁衍生pH响应光功能分子抑制伤口细菌感染的微针贴片无缝集成了感染微环境激活的荧光成像和光动力疗法和一氧化碳气体协同抗菌活性。本发明提出了一种基于花青素衍生物的高性能光疗剂，可以感知并动态调整其荧光和PDT特性，以响应感染微环境中的酸度变化。随后将疏水探针与活性氧反应性CO供体共同组装，形成生物相容性治疗纳米系统，并将其进一步封装在透明质酸微针贴片中，以增强其在感染部位的机械穿透和控释活性。PDT与CO气体级联产生的结合产生了强有力的细菌消除效应，显著抑制细菌生物膜介导的感染。巧妙地将感染激活生物成像与协同抗菌治疗相结合，为有效和个性化管理感染相关疾病提供了巨大的潜力。
• CO₂ Triggering and Controlling Orthogonally Multiresponsive Photochromic Systems
  作者：Tamim A. Darwish、Richard A. Evans、Michael James、Nino Malic、Gerry Triani、Tracey L. Hanley

  DOI：10.1021/ja1013322

  日期：2010.8.11

  We report a new generic method of reversibly controlling the photochromism of spiropyrans. It was found that the photochromic effect of spiropyrans can be reversibly switched on and off by addition and removal of carbon dioxide (CO2) to spiropyran in alcohol solutions containing an amidine (i.e., DBU) that acts as a CO2 sensitizer. Spiropyrans are not photochromic in the presence of DBU but photochromic when CO2 is subsequently added to the solution. The CO2 is readily removed by inert gas bubbling, thus allowing facile activation and deactivation of the photochromic effect. Carbon dioxide, without the presence of the sensitizing amidine, had no effect on photochromism of the spiropyrans. Other photochromic dyes classes such as spirooxazines and chromenes are not affected by this CO2/DBU stimulus. As a result, orthogonal activation of mixtures of spirooxazines and spiropyrans was achieved to provide four color states (clear, yellow, green, and blue) by varying the combinations of the stimuli of UV, visible light, CO2, and CO2 depleted. This finding now permits the many applications using spiropyrans to be CO2 responsive.
• Synthesis of Spiropyrans As Building Blocks for Molecular Switches and Dyads
  作者：Christoph Beyer、Hans-Achim Wagenknecht

  DOI：10.1021/jo100309r

  日期：2010.4.16

  The synthesis of spiropyrans was improved significantly with use of ultrasonic radiation. To show the broad applicability of this methodology a range of spiropyrans were prepared which are equipped with iodo, hydroxyl, ethinyl, or azido groups as potential building blocks for conjugation to functional π-systems or biopolymers. Representatively, the conjugation chemistry was demonstrated for the preparation

  螺吡喃的合成通过使用超声辐射而得到显着改善。为了显示该方法的广泛适用性，制备了一系列螺并吡喃并带有碘，羟基，乙炔基或叠氮基，作为与功能性π-系统或生物聚合物结合的潜在结构单元。代表性地，证明了通过“点击”型环加成反应制备具有with，per和尼罗红的螺吡喃共轭物的共轭化学。这些分子二元化合物通过光谱学表征。
• Synthesis of DNA with Spirobenzopyran as an Internal Covalent Modification
  作者：Hans-Achim Wagenknecht、Christoph Beyer

  DOI：10.1055/s-0029-1219924

  日期：2010.6

  The photochromic spirobenzopyran was incorporated as an internal modification into oligonucleotides by two different synthetic strategies: For the first route the spiropyran phosphoramidite was synthesized as a DNA building block, whereas for the second route the postsynthetic ‘click’-type ligation was applied. Photo­induced ring opening of the chromophore could not be achieved in duplex DNA.

  通过两种不同的合成策略，光致变色螺吡喃被作为内部修饰引入到寡核苷酸中：第一条路线是将螺吡喃膦酰胺合成作为DNA构建模块，而第二条路线则采用了后合成“点击”型连接反应。在双链DNA中，色素的光诱导开环未能实现。