2-(2-(tert-butyl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione | 251359-13-4

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(2-(tert-butyl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione
• 英文别名: 2-(2-tert-butyl-6-methyl-4H-pyran-4-ylidene)-2H-indene-1,3-dione；2-(2-tert-butyl-6-methylpyran-4-ylidene)-indane-1,3-dione；2-(2-Tert-butyl-6-methylpyran-4-ylidene)indene-1,3-dione
• CAS: 251359-13-4
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: FLQVPDGMSILBDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  393.0±42.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(tert-butyl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione 、 N,N-二乙基-4-氨基苯甲醛 在 哌啶 作用下， 以 乙腈 为溶剂， 以42%的产率得到(E)-2-(2-tert-butyl-6-(4-diethylaminostyryl)-4H-pyran-4-ylidene)-1,3-indanedione
  参考文献：
  名称：

  New one- and two-dimensional 4H-pyranylidene NLO-phores

  摘要：

  Dipolar, V-shaped compounds derived from 4H-pyranylidene-linked acceptors have been synthesized, and their linear and nonlinear optical properties (displaying mu beta values up to 3000 x 10(-48) esu) have been compared to those of analogous one-dimensional derivatives. The pyranylidene ring behaves strictly as a spacer, and not as a donor group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.197

文献信息

• 一种喹啉衍生物及其用途
  申请人：中国人民解放军军事科学院军事医学研究院

  公开号：CN110642845B

  公开（公告）日：2021-01-05

  本发明提供通式a化合物，其中取代基如说明书所定义。本发明还涉及所述化合物及其药学上可接受的加成盐用于氧化还原指示剂和OFF‑ON型近红外荧光诊断试剂的用途。
• Fine tuning of the photophysical and electroluminescent properties of DCM-type dyes by changing the structure of the electron-donating group
  作者：Yi-Shan Yao、Qian-Xiong Zhou、Xue-Song Wang、Yue Wang、Bao-Wen Zhang

  DOI：10.1039/b604563d

  日期：——

  Using 2H-indene-1,3-dione as an electron-withdrawing group and aromatic amines of different structures as electron-donating groups, four new DCM-type dyes, IN-1, IN-2, IN-3, and IN-4, were designed and synthesized for application in organic light-emitting diodes (OLEDs) as red light-emitting materials. IN-2 exhibits a red shift in fluorescence but a blue shift in absorption with respect to IN-1. Similarly, IN-4 exhibits a red shift in fluorescence but a blue shift in absorption with respect to IN-3. These unique photophysical properties were utilized to optimize the electroluminescence color purity and efficiency of these red emitters in OLEDs. In EL devices with the configuration of ITO/NPB (60 nm)/Alq3 (or Gaq3) : red dopant (2.0 wt%) (7 nm)/BCP (12 nm)/Alq3 (45 nm)/LiF (0.3 nm)/Al (300 nm), IN-3 in Alq3 and IN-1 in Gaq3 show CIE coordinates of (0.64, 0.36) and (0.65, 0.34), and current efficiencies of 3.24 cd A−1 and 3.02 cd A−1, respectively, much better than the other guest/host combinations. This can be ascribed to the good spectrum overlap either between IN-3 and Alq3 or between IN-1 and Gaq3, indicating that the absorption spectrum has the same importance as the fluorescence spectrum in the improvement of color purity of red emitters.

  使用2H-茚-1,3-二酮作为电子吸引基，与不同结构的芳香胺作为电子供给基，设计并合成了四种新的DCM型染料IN-1、IN-2、IN-3和IN-4，作为有机发光二极管（OLEDs）中的红光发射材料。相较于IN-1，IN-2在荧光方面显示出红移，而在吸收方面则呈现蓝移。类似地，IN-4相对于IN-3在荧光方面显示红移，而在吸收方面呈现蓝移。这些独特的光物理特性被用来优化这些红色发射体在OLED中的电致发光颜色纯度和效率。在配置为ITO/NPB（60 nm）/Alq3（或Gaq3）:红色掺杂剂（2.0 wt%）（7 nm）/BCP（12 nm）/Alq3（45 nm）/LiF（0.3 nm）/Al（300 nm）的EL器件中，IN-3在Alq3中和IN-1在Gaq3中显示出CIE坐标（0.64, 0.36）和（0.65, 0.34），电流效率分别为3.24 cd A−1和3.02 cd A−1，远优于其他掺杂组合。这可归因于IN-3与Alq3之间或IN-1与Gaq3之间良好的光谱重叠，表明吸收光谱在提升红色发射体颜色纯度方面与荧光光谱同样重要。
• Carbazole-based small molecules for vacuum-deposited organic photovoltaic devices with open-circuit voltage exceeding 1 V
  作者：Yuan Jay Chang、Jung-Lien Hsu、Yi-Hua Li、Sajal Biring、Tzu-Hung Yeh、Jhih-Yan Guo、Shun-Wei Liu

  DOI：10.1016/j.orgel.2017.05.007

  日期：2017.8

  Fabrication of vacuum deposited small molecules organic solar cell with open-circuit voltage (Voc) exceeding 1 V is crucial in advancing the applications of organic photovoltaics (OPVs). Here, a novel carbazole-based donor-π bridge-acceptor (D-π-A) of p-type material (F-series) in combination with fullerene derivative C60 or C70 as n-type material for bulk-heterojunction OPVs with the structure of

  开路电压（V oc）超过1 V的真空沉积小分子有机太阳能电池的制造对于推进有机光伏（OPV）的应用至关重要。在这里，一种新型的咔唑基供体-π桥受体（D-π-A）是p型材料（F系列）与富勒烯衍生物C 60或C 70组合作为本体异质结OPV的n型材料具有ITO / MoO 3（15 nm）/ F系列供体的结构：C 60或C 70（40或80nm）/ BCP（7nm）/ Ag（120nm）已被提出。具有由F1和电子受体C70组成的供体层的真空沉积小分子OPV表现出4.93％的高功率转换效率（PCE）。OPV的较高PCE归因于1.02 V的大V oc值。使用随时间变化的密度泛函理论模型和B3LYP功能对光物理性质进行分析，证实了实验结果，并为提高Voc的V oc提供了证据。 OPV。
• A novel strategy for the functionalization and design of 4-methylene-4<i>H</i>-pyran merocyanines <i>via</i> enamination and 1,8-conjugate addition
  作者：Dmitrii L. Obydennov、Alena E. Simbirtseva、Alexander S. Shirinkin、Mikhail Y. Kornev、Vyacheslav Y. Sosnovskikh

  DOI：10.1039/d2ob01862d

  日期：——

  ubstituted pyrans are reactive intermediates and can be considered as a convenient synthetic tool for the construction of new merocyanines with tunable fluorescence (417–628 nm). The main strategies for the modification of the pyran moiety have been determined for the construction and targeted design of fluorophores. Pyrans bearing two enamine moieties demonstrate significant light extinction coefficients

  4-Methylene-4 H - pyrans 是流行的部花青染料，但它们的功能化受到与芳香醛的 Knoevenagel 缩合的限制。在这项工作中，我们开发了一种基于烯化和随后的二甲基氨基亲核取代的新型吡喃荧光团构建方法1,8-共轭添加/消除。这种方法包括选择性转换，导致以前未知的对称和不对称结构。二甲氨基乙烯基取代的吡喃是反应性中间体，可被视为一种方便的合成工具，用于构建具有可调荧光（417-628 nm）的新部花青。吡喃部分修饰的主要策略已确定用于荧光团的构建和靶向设计。带有两个烯胺部分的吡喃表现出显着的消光系数（高达 116 000 M -1 cm -1)、高量子产率（高达 69%）和大斯托克斯位移（高达 152 nm），因为它们具有很强的推挽性质。密度泛函理论 (DFT) 计算用于解释制备的部花青的结构和光物理特征。所开发的方法可以被视为一个有用的平台，可进一步将 4-亚甲基-4
• Linear and V-Shaped Nonlinear Optical Chromophores with Multiple 4<i>H</i>-Pyran-4-ylidene Moieties
  作者：Raquel Andreu、Elena Galán、Javier Garín、Vanessa Herrero、Edurne Lacarra、Jesús Orduna、Raquel Alicante、Belén Villacampa

  DOI：10.1021/jo902670z

  日期：2010.3.5

  A simple synthesis of dipolar one- and two-dimensional chromophores bearing two or three 4H-pyran-4-ylidene moieties is reported. Whereas the pyranylidene fragments acting as donors are proaromatic, the spacer one is not. In the linear derivatives, Chain elongation gives rise to a sharp increase in the second order nonlinear optical responses, but some V-shaped derivatives display first hyperpolarizabilities (beta) lower than those of their linear analogues. This uncommon feature lends experimental support to previous theoretical studies on the relative contribution and sign of the beta-tensor components.