2-hydroxyethyl 4-hydroxy-1-phenyl-2-naphthoate | 290349-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxyethyl 4-hydroxy-1-phenyl-2-naphthoate
• 英文别名: 2-Hydroxyethyl 4-hydroxy-1-phenylnaphthalene-2-carboxylate
• CAS: 290349-01-8
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: QVYIWSYLRDJJCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 4-hydroxy-1-phenyl-2-naphthoate 、 1,1-双(4-甲氧基苯基)-2-丙炔-1-醇 在 4-甲基苯磺酸吡啶 、 原甲酸三甲酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.67h， 以61%的产率得到2-hydroxyethyl 2,2-bis(4-methoxyphenyl)-6-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylate
  参考文献：
  名称：

  Optimizing the photochromic performance of naphthopyrans in a rigid host matrix using poly(dimethylsiloxane) conjugation

  摘要：

  一系列甲氧基取代的2,2-二芳基-2H-萘并吡喃光致变色染料被合成并通过引入羟基功能性，以便随后将其固定到柔性的聚二甲基硅氧烷低聚物中。研究了生成的PDMS-萘并吡喃共轭物在热固性基质中的光致变色性能，并与非共轭、电子等效的对照染料进行了比较。发现着色和褪色的速度都大幅提高，关键的褪色半衰期T1/2减少了42-80%。PDMS共轭在刚性基质中提供的类似溶液性能的程度，参考了对照染料在溶液中的褪色性能进行了考察，发现范围从20%到90%不等。这些测量结果被认为受到光致变色染料的电子性质和立体相互作用的影响。

  DOI：

  10.1039/b904345d
• 作为产物：
  描述：

  1-phenyl-4-hydroxy-2-naphthoic acid 、 2-溴乙醇 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以93%的产率得到2-hydroxyethyl 4-hydroxy-1-phenyl-2-naphthoate
  参考文献：
  名称：

  Optimizing the photochromic performance of naphthopyrans in a rigid host matrix using poly(dimethylsiloxane) conjugation

  摘要：

  一系列甲氧基取代的2,2-二芳基-2H-萘并吡喃光致变色染料被合成并通过引入羟基功能性，以便随后将其固定到柔性的聚二甲基硅氧烷低聚物中。研究了生成的PDMS-萘并吡喃共轭物在热固性基质中的光致变色性能，并与非共轭、电子等效的对照染料进行了比较。发现着色和褪色的速度都大幅提高，关键的褪色半衰期T1/2减少了42-80%。PDMS共轭在刚性基质中提供的类似溶液性能的程度，参考了对照染料在溶液中的褪色性能进行了考察，发现范围从20%到90%不等。这些测量结果被认为受到光致变色染料的电子性质和立体相互作用的影响。

  DOI：

  10.1039/b904345d

文献信息

• POLYMERIZABLE POLYALKOXYLATED NAPHTHOPYRANS
  申请人：PPG Industries Ohio, Inc.

  公开号：EP1112263A1

  公开（公告）日：2001-07-04
• US6113814A
  申请人：——

  公开号：US6113814A

  公开（公告）日：2000-09-05
• [EN] POLYMERIZABLE POLYALKOXYLATED NAPHTHOPYRANS<br/>[FR] NAPHTHOPYRANES POLYALCOXYLES POLYMERISABLES
  申请人：PPG IND OHIO INC

  公开号：WO2000015629A1

  公开（公告）日：2000-03-23

  Described are novel photochromic polymerizable polyalkoxylated naphthopyran compounds, examples of which are certain 2H-naphtho[1,2-b]pyrans, 3H-naphtho[2,1-b]pyrans and indeno[2,1-f]naphtho[1,2-b]pyrans each having at least one polyalkoxylated substituent of from 1 to 50 alkoxy units per substituent which is end-capped with a polymerizable group. Specific substituents are also present on the naphtho, indeno and pyrano portions of the compounds. These compounds may be represented by graphic formulae (I), (II) or (III). Also described are various substrates, e.g., paper, glass, polymeric organic materials, etc., that contain or that are coated with such compounds. Optically clear articles such as contact lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., certain other naphthopyrans, indenonaphthopyrans, benzopyrans, oxazine-type compounds, etc., are also described.
• Optimizing the photochromic performance of naphthopyrans in a rigid host matrix using poly(dimethylsiloxane) conjugation
  作者：Francesca Ercole、Nino Malic、Thomas P. Davis、Richard A. Evans

  DOI：10.1039/b904345d

  日期：——

  A series of methoxy substituted 2,2-diaryl-2H-naphthopyran photochromic dyes were assembled incorporating hydroxy functionality to allow their subsequent attachment to flexible poly(dimethylsiloxane) oligomers. The photochromic performance of the generated PDMS–naphthopyran conjugates was studied in a thermoset host matrix and compared to non-conjugated, electronically equivalent control dyes. Both coloration and decoloration speeds were found to be greatly improved with critical T1/2 decoloration times reduced by 42–80%. The extent of solution-like performance provided by PDMS conjugation in the rigid host was examined with reference to the fade performance of control dyes in solution, and found to range from 20 to 90%. These measures are believed to be influenced by the electronic nature and steric interactions of the photochromic dyes.

  一系列甲氧基取代的2,2-二芳基-2H-萘并吡喃光致变色染料被合成并通过引入羟基功能性，以便随后将其固定到柔性的聚二甲基硅氧烷低聚物中。研究了生成的PDMS-萘并吡喃共轭物在热固性基质中的光致变色性能，并与非共轭、电子等效的对照染料进行了比较。发现着色和褪色的速度都大幅提高，关键的褪色半衰期T1/2减少了42-80%。PDMS共轭在刚性基质中提供的类似溶液性能的程度，参考了对照染料在溶液中的褪色性能进行了考察，发现范围从20%到90%不等。这些测量结果被认为受到光致变色染料的电子性质和立体相互作用的影响。