2-(3',3'-二甲基-6-硝基螺[色烯-2,2'-吲哚]-1'-基)乙基甲基丙烯酸酯 | 25952-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-(3',3'-二甲基-6-硝基螺[色烯-2,2'-吲哚]-1'-基)乙基甲基丙烯酸酯
• 英文名称: 1'-(2-methacryloxyethyl)-3',3'-dimethyl-6-nitrospiro(2H-1-benzopyran-2,2'-indoline)
• 英文别名: 1'-(2-methacryloyloxyethyl)-3,3'-dimethyl-6-nitrospiro[2H-1-benzopyran-2,2'-indoline]；2-(3',3'-Dimethyl-6-nitrospiro[chromene-2,2'-indolin]-1'-yl)ethyl methacrylate；2-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)ethyl 2-methylprop-2-enoate
• CAS: 25952-50-5
• 化学式: C₂₄H₂₄N₂O₅
• 分子量: 420.465
• InChiKey: JRQCDWUVZUDZOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3',3'-二甲基-6-硝基螺[色烯-2,2'-吲哚]-1'-基)乙基甲基丙烯酸酯 以 丙酮 为溶剂， 反应 0.02h， 生成 2-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]ethyl 2-methylprop-2-enoate
  参考文献：
  名称：

  Synthesis and photochromic properties of methacryloxy 6-nitrospirobenzopyrans

  摘要：

  The synthesis. and spectroscopic characterization of several methacryloxy-modified spiropyran dyes is reported. The dyes were found to have similar photochromic isomerization rates relative to a commercially available reference compound in solution. The methacryloxy-modified dyes were also successfully incorporated into polymer matrices, where they retained their ability to photoisomerize and complex with cobalt (II) and zinc (II) ions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.03.010
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 哌啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 2-(3',3'-二甲基-6-硝基螺[色烯-2,2'-吲哚]-1'-基)乙基甲基丙烯酸酯
  参考文献：
  名称：

  Development of light-responsive porous polycarbonate membranes for controlled caffeine delivery

  摘要：

  为了控制咖啡因的释放，我们开发了光响应膜。与日光下的测量结果相比，在紫外线照射下，膜的咖啡因渗透阻力降低了约 97%。这是通过将具有光致变色单元的聚合物接枝到轨迹边缘聚碳酸酯膜上实现的。多孔聚碳酸酯膜上的共价连接涂层是通过等离子活化膜表面，然后进行等离子诱导接枝聚合而获得的。在涂层过程中对螺环化合物进行共聚，以及用螺环吡喃对预制涂层进行后修饰，均可获得光致变色膜。在共聚过程中，成功合成了五种具有光致变色作用的甲基丙烯酸和丙烯酸螺吡喃以及螺恶嗪。此外，我们还合成了一种具有羧酸功能的螺吡喃，用于后改性工艺。这使我们能够对含有醇或胺基团的聚合物材料进行后修饰，从而获得光致变色材料。对这些光响应膜进行紫外线照射后，膜会产生强烈的颜色变化，表面张力降低，从而降低了咖啡因的抗渗透性。利用 XPS 测定涂层的元素组成、接触角测量表面张力、固态 UV/VIS 测量动力学和稳定性能，以及双光子显微镜测定光致变色物质在多孔膜中的定位。

  DOI：

  10.1039/c3ra44399j

文献信息

• 一种光活性纳米复合物及其制备方法与应用
  申请人：南京大学

  公开号：CN107970448B

  公开（公告）日：2020-12-15

  本发明公开了一种光活性纳米复合物及其制备方法与应用，该纳米复合物包括核酸分子和阳离子聚合物，阳离子聚合物由正电性链段、亲水性链段和光敏性链段组成，光敏性链段为螺吡喃链段；制备方法是将阳离子聚合物溶液置于紫外光下照射，然后与核酸分子混合，静置即得。本发明的优点是通过阳离子聚合物与带负电的核酸分子的自发相互作用形成光活性纳米复合物，制备方法、过程简单，既可以作为光控开关又可以作为光敏剂，在指导疾病诊疗与光动力治疗领域有广泛前景。
• Light-responsive amphiphilic copolymer coated nanoparticles as nanocarriers and real-time monitors for controlled drug release
  作者：Qingjian Xing、Najun Li、Dongyun Chen、Wenwei Sha、Yang Jiao、Xiuxiu Qi、Qingfeng Xu、Jianmei Lu

  DOI：10.1039/c3tb21269f

  日期：——

  Herein, light-responsive nanocarriers based on hollow mesoporous silica (HMS) nanoparticles modified with spiropyran-containing light-responsive copolymer (PRMS-FA) were fabricated via a simple self-assembly process. HMS modified with long-chain hydrocarbon octadecyltrimethoxysilane was an ideal base material owing to its good biocompatibility and drug capability. The spiropyran-containing amphiphilic copolymer could shift its hydrophilic–hydrophobic balance to become hydrophilic upon UV (λ = 365 nm) irradiation and then break away from the hydrophobic surface of the HMS core, followed by the uncaging and release of the pre-loaded anticancer drug. Simultaneously, the fluorescence resonance energy transfer (FRET) process based on the structural transformation of PRMS-FA was observed, which could act as a real-time monitor for the light-controlled drug release. Our model experiments in vitro tested and verified that this composite nanocarrier has good biocompatibility, active tumour targeting to the folate receptor over-expressed in tumour cells, is non-toxic to normal cells and that light-controlled drug release with real-time monitoring can be achieved.

  本文通过简单的自组装工艺，制备了基于含螺吡喃光响应共聚物（PRMS-FA）修饰的中空介孔二氧化硅（HMS）纳米颗粒的光响应纳米载体。长链碳氢化合物十八烷基三甲氧基硅烷修饰的 HMS 具有良好的生物相容性和药物功能，是一种理想的基础材料。在紫外线（λ = 365 nm）照射下，含有螺吡喃的两亲共聚物可改变其亲水-疏水平衡，变得亲水，然后脱离 HMS 内核的疏水表面，释放出预载的抗癌药物。与此同时，我们还观察到了基于 PRMS-FA 结构转变的荧光共振能量转移（FRET）过程，该过程可作为光控药物释放的实时监测器。我们的体外模型实验测试并验证了这种复合纳米载体具有良好的生物相容性、对肿瘤细胞中过度表达的叶酸受体具有积极的肿瘤靶向性、对正常细胞无毒，并且可以实现实时监测的光控药物释放。
• Synthesis of Photochromic Monomers Derived from 1′‐(2‐Methacryloxyethyl)‐3,3‐Dimethyl‐2‐[2H]‐Spirobenzopyran Indoline
  作者：Luis Ernesto Elizalde、Raquel Ledezma、Raúl G. López

  DOI：10.1081/scc-200049808

  日期：2005.3

  Abstract The syntheses of five photochromic monomers derived from N‐ (2‐methacryloxyethyl)‐3′, 3′‐dimethylspiro‐[2H‐1] benzopyrane‐2, 2′‐indoline are reported. The preparation of these compounds involves the heterogeneous reaction between the N‐(hydroxyethyl)‐2,3,3‐trimethylindolenonium bromide and methacryloyl chloride in a polar solvent. The esterificated salt is easily purified by crystallization

  摘要 报道了衍生自 N-(2-甲基丙烯酰氧基乙基)-3', 3'-二甲基螺-[2H-1] 苯并吡喃-2, 2'-二氢吲哚的五种光致变色单体的合成。这些化合物的制备涉及 N-(羟乙基)-2,3,3-三甲基吲哚溴铵和甲基丙烯酰氯在极性溶剂中的多相反应。酯化盐很容易通过在氯仿-己烷中结晶来纯化。与适当的 2-羟基苯甲醛进一步缩合产生高产率的光致变色单体。该方法也可用于制备其他螺吡喃衍生物。
• Development of light-responsive porous polycarbonate membranes for controlled caffeine delivery
  作者：Lukas Baumann、Katrin Schöller、Damien de Courten、Dominik Marti、Martin Frenz、Martin Wolf、René M. Rossi、Lukas J. Scherer

  DOI：10.1039/c3ra44399j

  日期：——

  For controlled caffeine release, light-responsive membranes were developed. It was possible to produce membranes that reduced their caffeine permeability resistance by about 97% when irradiated with UV-light compared to measurements at daylight. This was achieved by grafting polymers possessing photochromic units onto track-edged polycarbonate membranes. Covalently linked coatings on porous polycarbonate membranes were obtained by plasma activation of the membrane surface followed by plasma-induced graft polymerization. Copolymerization of spiro-compounds during the coating process as well as postmodification of preformed coatings with spiropyran resulted in photochromic membranes. For the copolymerization process, the synthesis of five photochromic methacrylic and acrylic spiropyrans and spirooxazines was successfully performed. Additionally, a spiropyran with carboxylic acid functionality was synthesized for the postmodification process. This enabled us to postmodify polymeric materials containing alcohol or amine groups to obtain photochromic materials. UV-irradiation of these light-responsive membranes resulted in a strong colouration of the membrane, in a reduction of surface tension, which resulted in a decreased caffeine permeability resistance. The membranes were characterized using XPS for the elemental composition of the coating, contact angle measurements for the surface tension, solid-state UV/VIS measurements for the determination of the kinetic and stability properties, and two-photon microscopy for the localisation of the photochromic substance in the porous membrane.

  为了控制咖啡因的释放，我们开发了光响应膜。与日光下的测量结果相比，在紫外线照射下，膜的咖啡因渗透阻力降低了约 97%。这是通过将具有光致变色单元的聚合物接枝到轨迹边缘聚碳酸酯膜上实现的。多孔聚碳酸酯膜上的共价连接涂层是通过等离子活化膜表面，然后进行等离子诱导接枝聚合而获得的。在涂层过程中对螺环化合物进行共聚，以及用螺环吡喃对预制涂层进行后修饰，均可获得光致变色膜。在共聚过程中，成功合成了五种具有光致变色作用的甲基丙烯酸和丙烯酸螺吡喃以及螺恶嗪。此外，我们还合成了一种具有羧酸功能的螺吡喃，用于后改性工艺。这使我们能够对含有醇或胺基团的聚合物材料进行后修饰，从而获得光致变色材料。对这些光响应膜进行紫外线照射后，膜会产生强烈的颜色变化，表面张力降低，从而降低了咖啡因的抗渗透性。利用 XPS 测定涂层的元素组成、接触角测量表面张力、固态 UV/VIS 测量动力学和稳定性能，以及双光子显微镜测定光致变色物质在多孔膜中的定位。
• MOLECULARLY IMPRINTED SMART POLYMERS (MISPs)
  申请人：Grynszpan Flavio

  公开号：US20110166297A1

  公开（公告）日：2011-07-07

  Molecularly imprinted smart polymers (MISPs) are provided herein, as well as novel monomers for preparing MISPs, and processes for preparing MISPs. The MISPs can be used applications such as, for example, detecting/absorbing or isolating biological and non-biological agents. The MISPs described herein comprise responsive monomeric units which undergo a physico-chemical change (e.g., a bond formation or cleavage) in response to an external change, such that the MISP selectively binds to a target molecule and releases a bound target molecule in response to the external change.

  本文提供了分子印迹智能聚合物（MISPs），以及用于制备MISPs的新型单体和制备MISPs的过程。MISPs可用于检测/吸收或隔离生物和非生物试剂等应用。本文描述的MISPs包括响应性单体单元，其在响应外部变化时（例如，键的形成或断裂），使MISP选择性地结合到目标分子，并在响应外部变化时释放结合的目标分子。