3,3-diphenyl-8-formyl-[3H]-naphtho[2,1-b]pyran | 227471-74-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3,3-diphenyl-8-formyl-[3H]-naphtho[2,1-b]pyran
• 英文别名: 3H-Naphtho[2,1-b]pyran-8-carboxaldehyde, 3,3-diphenyl-；3,3-diphenylbenzo[f]chromene-8-carbaldehyde
• CAS: 227471-74-1
• 化学式: C₂₆H₁₈O₂
• 分子量: 362.428
• InChiKey: GZNJFTCWDTYMGY-UHFFFAOYSA-N

物化性质

• 沸点：
  561.5±50.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-diphenyl-8-formyl-[3H]-naphtho[2,1-b]pyran 在 正丁基锂 、 tert-butylammonium hexafluorophosphate(V) 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 生成 8-[1,2-Bis(1,3-benzodithiol-2-ylidene)-2-(3,3-diphenylbenzo[f]chromen-8-yl)ethyl]-3,3-diphenylbenzo[f]chromene
  参考文献：
  名称：

  一系列（1,4-二硫富富翁-6-基）取代的3 H-萘[ 2,1- b ]吡喃衍生物的合成，电化学和光致变色行为

  摘要：

  含有不同取代的二硫富烯基乙烯基单元的新3,3-二苯基-8-（1,4-二硫富烯基-6-基）-[ 3H ]-萘[ 2,1- b ]吡喃衍生物的合成，电化学和光致变色性质为描述。示出了电化学二聚化的一个实例，该实例提供了进入电活性双发色体系的途径。这样的系统可以研究光致变色和电化学性质的相互作用。

  DOI：

  10.1016/j.tet.2004.10.084
• 作为产物：
  描述：

  1,1-二苯基-2-丙炔-1-醇 在 正丁基锂 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,3-diphenyl-8-formyl-[3H]-naphtho[2,1-b]pyran
  参考文献：
  名称：

  Synthesis and reactivity of formyl-substituted photochromic 3,3-diphenyl-[3H]-naphtho[2,1-b]pyrans

  摘要：

  Synthetic accesses to formylated photochromic 3,3-diphenyl-[3H]-naphthopyrans (or 2H-benzochromenes) are developed through classical cyclization between appropriate hydroxynaphthaldehydes and 1,1-diphenylpropyne-1-ol and also via substituent transformations on the naphthopyran skeleton including bromine/lithium exchange and the oxidation of an hydroxymethyl group. Examples of formyl group reactivity (Wittig and Knoevenagel reactions, imine formation) from these compounds are given, showing their interest in the subsequent preparation of supramolecular systems involving a photoreactive entity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00245-8

文献信息

• Synthesis and optical properties of naphthopyran dyes conjugated with fluorescent stilbazolium moieties
  作者：Ingolf Kahle、Oliver Tröber、Hannes Richter、Stefan Spange

  DOI：10.1039/c3nj41130c

  日期：——

  The synthesis of new 3H-naphtho[2,1-b]pyran dyes substituted at position 8 of the naphthalene ring by either a stilbazolium or an 4-ethenyl-quinolinium group and their photochemical properties are described. In non-polar media the naphthopyran–stilbazolium conjugates do not show any photochromic response while the formation of the ring opened species is promoted in strong polar media. Additional investigations

  描述了一种新的3 H-萘[2,1- b ]吡喃染料的合成，该染料在萘环的8位被一个stilbazolium或4-ethenyl-quinolinium基团取代，及其光化学性质。在非极性介质中，萘并吡喃–噻唑鎓共轭物未显示任何光致变色反应，而在强极性介质中促进了开环物质的形成。与介孔MCM 41颗粒的孔内的新染料有关的其他研究表明，与溶液相比，光致变色现象显着增强。用紫外线照射时开环物质的产生伴随着荧光强度的降低，这可以通过用可见光照射来恢复。
• Synthesis and unexpected photochemical behaviour of biphotochromic systems involving spirooxazines and naphthopyrans linked by an ethylenic bridge
  作者：André Samat、Vladimir Lokshin、Karine Chamontin、David Levi、Gérard Pepe、Robert Guglielmetti

  DOI：10.1016/s0040-4020(01)00693-7

  日期：2001.8

  molecules taken individually, unusual photochromic behaviour has been detected with compounds for which a double bond of Z-configuration links both entities by the 5 or 5′ positions of the naphthalenic parts. Indeed, in this case the thermally stable uncoloured and coloured forms (bistable system) can be photochemically converted acting as photochemical switches.

  通过维蒂希反应，通过方便地官能化的螺[吲哚啉-萘并恶嗪]和萘并吡喃的偶联，制备了六种新的双光致变色化合物。与单独获取的分子相比，使用Z构型的双键通过萘部分的5或5'位置连接两个实体的化合物已检测到异常的光致变色行为。实际上，在这种情况下，可以将热稳定的无色和有色形式（双稳态体系）进行光化学转化，充当光化学开关。
• Study on the photochromism, photochromic fluorescence switch, fluorescent and colorimetric sensing for Cu2+ of naphthopyran-diaminomaleonitrile dyad and recognition Cu2+ in living cells
  作者：Heyang Zhang、Tianyuan Zhong、Nan Jiang、Zhuo Zhang、Xue Gong、Guang Wang

  DOI：10.1016/j.saa.2020.118191

  日期：2020.6

  A well-designed naphthopyran-diaminomaleonitrile dyad (sensor 1) has been synthesized successfully, its molecular structure was well characterized by NMR and mass spectrometry. Sensor 1 exhibits excellent photochromic and photochromic fluorescence switch performance with reversible color change and good fatigue resistance upon alternating ultraviolet irradiation and thermal bleaching. In addition, sensor 1 displayed excellent fluorescent and colorimetric sensing ability towards Cu2+ ions with high selectivity and sensitivity. The addition of 5.0 equiv. of Cu2+ ions into sensor 1 (1 x 10(-5)) in CH3CN solution significantly quenched the fluorescence of sensor 1 by 80.0%. Furthermore, the addition of Cu2+ ions also caused the complete disappearance of the absorbance band at 350-450 nm in absorbance spectra of sensor 1 and accompanied by the distinct color change form yellow to colorless. Job's plot, mass spectrometry, H-1 NMR titration and DFT calculations proved that sensing performance was attributed to the formation of 1:1 sensor 1-Cu2+ complexes. Sensor 1 can monitor the existence of Cu2+ ions in living cells via the fluorescence images. Sensor 1 showed great potential applications as chemosensor and photochromic materials. (C) 2020 Elsevier B.V. All rights reserved.
• Synthesis and reactivity of formyl-substituted photochromic 3,3-diphenyl-[3H]-naphtho[2,1-b]pyrans
  作者：Karine Chamontin、Vladimir Lokshin、Valérie Rossollin、André Samat、Robert Guglielmetti

  DOI：10.1016/s0040-4020(99)00245-8

  日期：1999.4

  Synthetic accesses to formylated photochromic 3,3-diphenyl-[3H]-naphthopyrans (or 2H-benzochromenes) are developed through classical cyclization between appropriate hydroxynaphthaldehydes and 1,1-diphenylpropyne-1-ol and also via substituent transformations on the naphthopyran skeleton including bromine/lithium exchange and the oxidation of an hydroxymethyl group. Examples of formyl group reactivity (Wittig and Knoevenagel reactions, imine formation) from these compounds are given, showing their interest in the subsequent preparation of supramolecular systems involving a photoreactive entity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis, electrochemical and photochromic behaviour of a series of (1,4-dithiafulven-6-yl)substituted 3H-naphtho[2,1-b]pyran derivatives
  作者：Aude-Emmanuelle Navarro、Fabrice Moggia、Corinne Moustrou、Arnault Heynderickx、Frédéric Fages、Philippe Leriche、Hugues Brisset

  DOI：10.1016/j.tet.2004.10.084

  日期：2005.1

  The synthesis and electrochemical and photochromic properties of new 3,3-diphenyl-8-(1,4-dithiafulven-6-yl)-[3H]-naphtho[2,1-b]pyran derivatives containing differently substituted dithiafulvenyl units are described. An example of electrochemical dimerization is shown which gives access to electroactive bichromophoric systems. Such systems could allow the study of the interplay of photochromic and electrochemical

  含有不同取代的二硫富烯基乙烯基单元的新3,3-二苯基-8-（1,4-二硫富烯基-6-基）-[ 3H ]-萘[ 2,1- b ]吡喃衍生物的合成，电化学和光致变色性质为描述。示出了电化学二聚化的一个实例，该实例提供了进入电活性双发色体系的途径。这样的系统可以研究光致变色和电化学性质的相互作用。