3-(4-methoxyphenyl)-3-phenyl-3H-naphtho[2,1-b]pyran | 149743-78-2

• 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-(4-methoxyphenyl)-3-phenyl-3H-naphtho[2,1-b]pyran
• 英文别名: 3-(4-Methoxyphenyl)-3-phenylbenzo[f]chromene
• CAS: 149743-78-2
• 化学式: C₂₆H₂₀O₂
• 分子量: 364.444
• InChiKey: QKSWQXUXRQUBIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-3-phenyl-3H-naphtho[2,1-b]pyran 在 polymethylmethacrylate 作用下， 生成
  参考文献：
  名称：

  Photochromic Properties of Naphthopyrans – PMMA Thin Film

  摘要：

  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.

  DOI：

  10.1080/15421400802697566
• 作为产物：
  描述：

  在 polymethylmethacrylate 作用下， 生成 3-(4-methoxyphenyl)-3-phenyl-3H-naphtho[2,1-b]pyran
  参考文献：
  名称：

  Photochromic Properties of Naphthopyrans – PMMA Thin Film

  摘要：

  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.

  DOI：

  10.1080/15421400802697566

文献信息

• The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans
  作者：Christopher D. Gabbutt、B. Mark Heron、Colin Kilner、Suresh B. Kolla

  DOI：10.1039/c0ob00141d

  日期：——

  trimethylsilylacetylide, react with either a 1- or 2- naphthol to afford photochromic 1,1-diarylvinyl substituted naphtho[1,2-b]- or naphtho[2,1-b]-pyrans respectively. Irradiation of solutions of these naphthopyrans results in reversible electrocyclic ring-opening to afford photomerocyanines which possess an extended conjugated system and show a bathochromically-shifted λmax relative to the non-vinyl substituted

  1,1,3-Triarylpent-4-en-1-yn-3-ols，通过Meyer-Schuster重排和随后的添加从1,1,3-triarylprop-2-yn-1-ols分两步有效地获得的 三甲基甲硅烷基乙炔锂，与1或2反应 萘酚 提供光致变色的1,1-二芳基乙烯基取代 萘酚[1,2- b ]-或萘并[2,1- b ]-吡喃。在可逆电环开环，这些萘结果的解决方案的照射，得到其具有延长的共轭体系photomerocyanines并显示出红移λ最大值相对于所述非乙烯基取代的类似物。
• A strategy for the design of photochromic naphthopyrans with large optical density at photosteady state and fast fading speed at ambient temperature in the dark
  作者：Kunpeng Guo、Yi Chen

  DOI：10.1039/c000610f

  日期：——

  A photochromic naphthopyran system in which both optical density and fading speed of colored forms are significantly increased has been described. 3-Aryl-3-(α-naphthalene)-3H-naphtho[2,1-b]pyrans showed thermal stability, and a large optical density of colored forms was obtained at ambient temperature. By attachment of an alkoxyl group to the α-naphthalene group, the fading speed of colored forms was dramatically increased, and the fading speed was increased with increase of the length of alkoxyl chain. The generic nature of the system is beneficial for both the design of naphthopyran molecules with large optical density and fast fading speed at ambient temperature and applications.

  研究人员描述了一种光致变色萘系化合物，在这种化合物中，有色形式的光密度和褪色速度都显著提高。3 芳基-3-(α-萘)-3H-萘并[2,1-b]吡喃具有热稳定性，在环境温度下可获得较大的有色光密度。通过在α-萘基团上连接烷氧基，有色形式的褪色速度大大加快，而且褪色速度随着烷氧基链长度的增加而加快。该体系的通用性既有利于设计光密度大、在常温下褪色速度快的萘分子，也有利于其应用。
• Photochromic blue light filtering materials and ophthalmic devices
  申请人：Jani M. Dharmendra

  公开号：US20050254003A1

  公开（公告）日：2005-11-17

  Polymeric compositions have photochromic and blue-light filtering ability and are useful in the manufacture of ophthalmic medical devices. The polymeric compositions comprise a photochromic material incorporated into polymeric host materials and are activatable by blue light having a first wavelength range to become photochromic, and are thereby capable of absorbing blue light in a second wavelength range. Methods of making the compositions comprise incorporating a photochromic material into a polymeric host material.

  聚合物组合物具有光致变色和蓝光过滤能力，并可用于制造眼科医疗器械。该聚合物组合物包括将光致变色材料并入聚合物基材料中，可以通过第一波长范围的蓝光激活变成光致变色，并且因此能够吸收第二波长范围的蓝光。制造该组合物的方法包括将光致变色材料并入聚合物基材料中。
• One-Pot Synthesis of Photochromic Naphthopyrans in the Solid State
  作者：Koichi Tanaka、Hiroko Aoki、Hiroyuki Hosomi、Shigeru Ohba

  DOI：10.1021/ol006038y

  日期：2000.7.1

  [GRAPHICS]p-TsOH catalyzed condensation reactions of 1,1-diaryl-2 propyn-1-ol (1) and 2-naphthol (2) in the solid state gave 3,3-diaryl-3H-naphtho[2,1-b]pyran (6) via Claisen rearrangement. Similar reactions of 1 with 2,6- (7) and 2,7-dihydroxynaphthalenes (8) afforded naphthodipyrane derivatives 9 and 10, respectively. Bis-naphthopyran derivatives 12 were also obtained by the reaction of 1,1,6,6-tetraaryl-2,5-hexadiyn-1,6 diol (II) and 2-naphthol (2) in the solid state.
• PHOTOCHROMIC NAPHTHOPYRAN COMPOUNDS
  申请人：PPG INDUSTRIES, INC.

  公开号：EP0613475B1

  公开（公告）日：1998-01-07