4-(2-methoxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one | 937049-93-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(2-methoxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one
• 英文别名: (5Z)-5-[(2-methoxyphenyl)methylidene]-2,3-dimethylimidazol-4-one
• CAS: 937049-93-9
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: OUFHRIPUWHUIOL-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-methoxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one 在 氘代甲醇-d 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Ortho Green Fluorescence Protein Synthetic Chromophore; Excited-State Intramolecular Proton Transfer via a Seven-Membered-Ring Hydrogen-Bonding System

  摘要：

  A structural isomer of the core chromophore (p-HBDI) in green fluorescence protein, o-HBDI, is synthesized. o-HBDI possesses a seven-membered-ring hydrogen bond, from which the excited-state intramolecular proton transfer takes place, resulting in a remarkable tautomer emission of similar to 605 nm.

  DOI：

  10.1021/ja070880i
• 作为产物：
  描述：

  邻甲基苄醇 在 氢氧化钾 、 sodium acetate 、 乙酸酐 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 8.0h， 生成 4-(2-methoxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  Ortho Green Fluorescence Protein Synthetic Chromophore; Excited-State Intramolecular Proton Transfer via a Seven-Membered-Ring Hydrogen-Bonding System

  摘要：

  A structural isomer of the core chromophore (p-HBDI) in green fluorescence protein, o-HBDI, is synthesized. o-HBDI possesses a seven-membered-ring hydrogen bond, from which the excited-state intramolecular proton transfer takes place, resulting in a remarkable tautomer emission of similar to 605 nm.

  DOI：

  10.1021/ja070880i

文献信息

• Excited-State Intramolecular Proton Transfer Molecules Bearing <i>o</i>-Hydroxy Analogues of Green Fluorescent Protein Chromophore
  作者：Wei-Ti Chuang、Cheng-Chih Hsieh、Chin-Hung Lai、Cheng-Hsuan Lai、Chun-Wei Shih、Kew-Yu Chen、Wen-Yi Hung、Yu-Hsiang Hsu、Pi-Tai Chou

  DOI：10.1021/jo2012384

  日期：2011.10.21

  resulting in a proton-transfer tautomer emission. Fluorescence upconversion dynamics have revealed a coherent type of ESIPT, followed by a fast vibrational/solvent relaxation (<1 ps) to a twisted (regarding exo-C(5)–C(4)–C(3) bonds) conformation, from which a fast population decay of a few to several tens of picoseconds was resolved in cyclohexane. Accordingly, the proton-transfer tautomer emission intensity

  合成了绿色荧光蛋白生色团的邻羟基类似物1a – g。通过X射线单晶分析，电化学和发光特性研究了它们的结构和电子性能。在固体和非极性溶剂中1a – g主要以Z的形式存在具有七元环氢键并经历激发态分子内质子转移（ESIPT）反应的构象异构体，导致质子转移互变异构体发射。荧光上转换动力学揭示了一种相干类型的ESIPT，随后是快速振动/溶剂弛豫（<1 ps）到扭曲（关于exo-C（5）–C（4）–C（3）键）构象，在环己烷中分辨出了几到几十皮秒的快速人口衰减。因此，质子互变异构体转移发射强度适中（0.08英寸1E）至弱（〜10 -4在1A）的环己烷。1g中更强的分子内氢键抑制芳基-烯烃键的旋转，从而导致发射互变异构体的高产率（Φ ˚F ≈0.2）。在固态下，由于抑制了exo-C（5）–C（4）–C（3）的旋转，对于1a – g，可获得强互变异构体发射，量子产率为0.1–0.9 。取决于取代基在HO
• COUPLED RECOGNITION/DETECTION SYSTEM FOR IN VIVO AND IN VITRO USE
  申请人：Cornell University

  公开号：US20190185434A1

  公开（公告）日：2019-06-20

  The present invention relates to novel fluorophores and their use in combination with novel nucleic acid molecules, called aptamers, that bind specifically to the fluorophore and thereby enhance the fluorescence signal of the fluorophore upon exposure to radiation of suitable wavelength. Molecular complexes formed between the novel fluorophores, novel nucleic acid molecules, and their target molecules are described, and the use of multivalent aptamer constructs as fluorescent sensors for target molecules of interest are also described.

  本发明涉及新型荧光物质及其与称为寡核苷酸的新型核酸分子结合使用，这些寡核苷酸能够特异性地结合到荧光物质上，从而在受到适当波长辐射照射时增强荧光物质的荧光信号。描述了新型荧光物质、新型核酸分子及其靶分子形成的分子复合物，还描述了多价寡核苷酸构建物作为感兴趣的靶分子的荧光传感器的使用。
• Coupled recognition/detection system for in vivo and in vitro use
  申请人：Jaffrey Samie R.

  公开号：US10316000B2

  公开（公告）日：2019-06-11

  The present invention relates to novel fluorophores and their use in combination with novel nucleic acid molecules, called aptamers, that bind specifically to the fluorophore and thereby enhance the fluorescence signal of the fluorophore upon exposure to radiation of suitable wavelength. Molecular complexes formed between the novel fluorophores, novel nucleic acid molecules, and their target molecules are described, and the use of multivalent aptamer constructs as fluorescent sensors for target molecules of interest are also described.

  本发明涉及新型荧光团及其与新型核酸分子（称为适配体）的结合使用，后者与荧光团特异性结合，从而在暴露于适当波长的辐射时增强荧光团的荧光信号。此外，还介绍了新型荧光团、新型核酸分子及其目标分子之间形成的分子复合物，以及多价适配体构建体作为荧光传感器用于检测感兴趣的目标分子的情况。
• US7196199B2
  申请人：——

  公开号：US7196199B2

  公开（公告）日：2007-03-27
• [EN] COUPLED RECOGNITION/DETECTION SYSTEM FOR IN VIVO AND IN VITRO USE<br/>[FR] SYSTÈME DE RECONNAISSANCE/DÉTECTION COUPLÉE POUR UNE UTILISATION IN VIVO ET IN VITRO
  申请人：UNIV CORNELL

  公开号：WO2010096584A1

  公开（公告）日：2010-08-26

  The present invention relates to novel fluorophores and their use in combination with novel nucleic acid molecules, called aptamers, that bind specifically to the fluorophore and thereby enhance the fluorescence signal of the fluorophore upon exposure to radiation of suitable wavelength. Molecular complexes formed between the novel fluorophores, novel nucleic acid molecules, and their target molecules are described, and the use of multivalent aptamer constructs as fluorescent sensors for target molecules of interest are also described.