1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one | 174093-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one
• 英文别名: 1-(3,3-Diphenyl-2-propen-1-ylidene)-2(1H)-naphthalenone
• CAS: 174093-00-6
• 化学式: C₂₅H₁₈O
• 分子量: 334.417
• InChiKey: CDBYWEZHMJURSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one 在 1-butyl-3-methylimidazolium camphorsulfonate 作用下， 25.0 ℃ 、600.01 MPa 条件下， 生成 3,3-二苯基-3H-萘并[2,1-b]吡喃
  参考文献：
  名称：

  First Observation for Dynamic Solvent Effect in Ionic Liquids

  摘要：

  我们观察到在离子液体中，压力对由2光化学生成的有色克罗梅1的热褪色速率的影响。随着压力的增加，在[C4-mim][CS]、[bzl-mim][Tf2N]和[mnp-mim][Tf2N]中，反应速率减缓，而在[C4-mim][Tf2N]中，反应速率随着压力的增加而增加。这些由压力引起的减缓，称为动态溶剂效应，源于溶剂的缓慢热波动。

  DOI：

  10.1246/cl.151169
• 作为产物：
  描述：

  3,3-二苯基-3H-萘并[2,1-b]吡喃 生成 1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one
  参考文献：
  名称：

  取代萘并吡喃化合物的合成及光致变色性能

  摘要：

  制备了一组在萘并吡喃骨架的5-位和6-位以及3-芳基部分的对位具有功能性取代基的3,3-二芳基-3 H-萘[2,1-b]吡喃化合物2-萘酚衍生物和1，1-二芳基丙-2-yn-1-ol衍生物之间的缩合反应。化合物的化学结构通过NMR和MS确认。确定了3,3-二苯基-6-吗啉代-3 H-萘[2,1-b]吡喃（4b）的晶体结构，并讨论了吡喃亚结构与光致变色的关系。还研究了光致变色性质，并且将有色形式的脱色动力学拟合至双指数模型。在这些化合物中，4b 由于有色形式的ΔOD大，被认为是最好的一种，这是光致变色材料中最重要的特性之一。

  DOI：

  10.1016/j.tet.2011.01.078

文献信息

• Synthesis and photochromic properties of substituted naphthopyran compounds
  作者：Zhen Wang、Qinghua Meng、Zhihui Zhang、Dingliang Fu、Wanbin Zhang

  DOI：10.1016/j.tet.2011.01.078

  日期：2011.3

  of 3,3-diaryl-3H-naphtho[2,1-b]pyran compounds with functional substituents at the 5- and 6-positions of the naphthopyran skeleton and the para positions at the 3-aryl moieties were prepared through condensation reactions between 2-naphthol derivatives and 1,1-diarylprop-2-yn-1-ol derivatives. The chemical structures of the compounds were confirmed by NMR and MS. The crystal structure of 3,3-diphen

  制备了一组在萘并吡喃骨架的5-位和6-位以及3-芳基部分的对位具有功能性取代基的3,3-二芳基-3 H-萘[2,1-b]吡喃化合物2-萘酚衍生物和1，1-二芳基丙-2-yn-1-ol衍生物之间的缩合反应。化合物的化学结构通过NMR和MS确认。确定了3,3-二苯基-6-吗啉代-3 H-萘[2,1-b]吡喃（4b）的晶体结构，并讨论了吡喃亚结构与光致变色的关系。还研究了光致变色性质，并且将有色形式的脱色动力学拟合至双指数模型。在这些化合物中，4b 由于有色形式的ΔOD大，被认为是最好的一种，这是光致变色材料中最重要的特性之一。
• SERS Study of 3,3-Diphenyl-naphtho[2,1-b]pyran: Another Evidence for Allenyl-Naphthol Involvement in the Photochromic Mechanism
  作者：F. Maurel、S. Lau Troung、J. P. Bertigny、R. Dubest、G. Lévi、J. Aubard、S. Delbaere、G. Vermeersch

  DOI：10.1080/15421400590946442

  日期：2005.5.1

  (SERS) was used to study the photochromic behaviour of 3,3-diphenyl-naphtho[2,1-b]pyran in acetonitrile solutions at room temperature. Analysis of SERS spectra of irradiated solutions (UV, UV + visible) has allowed us to separate the spectral contribution of the different photoproducts involved during the photochemical reaction and during thermal relaxation. These experiments demonstrate that, under successive

  摘要 表面增强拉曼散射 (SERS) 用于研究室温下 3,3-二苯基-萘并 [2,1-b] 吡喃在乙腈溶液中的光致变色行为。对辐照溶液（UV、UV + 可见光）的 SERS 光谱的分析使我们能够分离光化学反应和热弛豫过程中涉及的不同光产物的光谱贡献。这些实验表明，在连续的紫外线和可见光照射下，新物种 A 被积累，然后通过 TC 光部花青异构体松弛到初始封闭形式 (CF)。A 的 SERS 光谱与 CF 的光谱有几个相似之处，这表明 A 的结构接近封闭形式，苯基和萘部分之间没有共轭。在最近的类似核磁共振实验的基础上，
• Photochromic Properties of Naphthopyrans – PMMA Thin Film
  作者：Kunpeng Guo、Yi Chen

  DOI：10.1080/15421400802697566

  日期：2009.3.19

  A class of naphthopyran derivatives (3a-10a) with electron-donating and electron-acceptor substituent is prepared by condensation of 1,2-diaryl-2-propyn-1-ol with beta-naphthol in the presence of pyridinium para-toluenesulfonate (PPTS) as catalyst. All compounds go ring-opening isomerization in polymethylmethacrylate (PMMA) matrix with UV light irradiation (30 watt) and the maximum absorption of ring-opening isomers is at the range of 426-556 nm. Ring-opening isomers are completely back to ring-closing isomers when samples are kept in darkness, the bleach rate of ring-opening isomers in PMMA film increased significantly when temperature is more than 45 degrees C. Fatigue testing showed that no significant change of optical density was detected after 10 cycles.
• Synthesis of heterocyclic chromenes via Buchwald C–N coupling and the substituent effect on their photochromic properties
  作者：Ekaterina A. Shilova、Gérard Pèpe、André Samat、Corinne Moustrou

  DOI：10.1016/j.tet.2008.07.116

  日期：2008.10

  Synthesis of series of new heterocyclic [2]H- and [3]H-chromenes via Buchwald C-N coupling is described. Introduction of heterocyclic substituent to 6-position of benzopyrans and in 8-position of naphthopyrans led to significant bathochromic shift (up to 154 nm) in the spectra of their open forms. Substituted benzopyrans display high colorability values along with acceptable resistance to fatigue. By using judicious substituents, the absorption range of this type of pyrans can be tuned according to the nature of the heterocyclic unit, and the photochromic properties of pyrans could be adjusted to desired values. (C) 2008 Elsevier Ltd. All rights reserved.
• Spectral manifestation of protonation of photochromic naphthopyrans
  作者：Alexander М. Gorelik、Оlga V. Venidiktova、Оlga I. Kobeleva、Тatyana М. Valova、Valery А. Barachevsky

  DOI：10.1016/j.dyepig.2020.108833

  日期：2021.1

  The formation of proton complexes of the photoinduced colored open form of naphthopyrans in solutions was first discovered and investigated by spectral-kinetic method. The complexes exhibit a new absorption band in the visible region, which is bathochromically shifted relative to the absorption band of the photoinduced colored open form. With an increase in the concentration of perchloric or hydrochloric acid, this long-wavelength absorption band appears immediately after the addition of acids to solutions of photochromic compounds. The protonation efficiency depends on the strength of the acids.