4-(乙酰基氧基)-6-甲氧基-2-萘羧酸乙酯 | 151502-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-(乙酰基氧基)-6-甲氧基-2-萘羧酸乙酯
• 英文名称: ethyl 4-acetoxy-6-methoxynaphthalene-2-carboxylate
• 英文别名: ethyl 4-acetoxy-6-methoxy-2-naphthoate；4-(Acetyloxy)-6-methoxy-2-naphthalenecarboxylic acid ethyl ester；ethyl 4-acetyloxy-6-methoxynaphthalene-2-carboxylate
• CAS: 151502-73-7
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: FOYJBOIIRSAMNO-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  439.2±30.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(乙酰基氧基)-6-甲氧基-2-萘羧酸乙酯 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以75%的产率得到4-羟基-6-甲氧基-2-萘羧酸乙酯
  参考文献：
  名称：

  Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark, Heterocycles, 2004, vol. 63, # 3, p. 567 - 582

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-4-tert-butyl 1-ethyl 2-(4-methoxybenzylidene)succinate 在 水 、 potassium acetate 、 三氟乙酸 作用下， 反应 3.0h， 生成 4-(乙酰基氧基)-6-甲氧基-2-萘羧酸乙酯
  参考文献：
  名称：

  AN EFFICIENT METHOD FOR THE SYNTHESIS OF SUBSTITUTED 4-ACETOXYNAPHTHALENE-2-CARBOXYLATE ESTERS, ETHYL 4-ACETOXYBENZOFURAN-6-CARBOXYLATE, AND ETHYL 4-ACETOXYBENZOTHIOPHENE-6-CARBOXYLATE

  摘要：

  DOI：

  10.1515/hc.2003.9.6.587

文献信息

• 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。
• Neutral coloring photochromic 2H-naphtho[1,2-b] pyrans and heterocyclic pyrans
  申请人：James Robinson Limited

  公开号：US06248264B1

  公开（公告）日：2001-06-19

  Compositions comprising a naphtho [1,2-b]pyran of formula (I): wherein R7 and/or R9 is hydrogen or an amino group provided that R7 and R9 are not both hydrogen, and the other substituents are as defined in the specifcation.

  本发明涉及一种萘并[1,2-b]吡喃化合物，其化学式为（I）：其中R7和/或R9是氢或氨基，但R7和R9不能同时是氢，其它取代基如规范中所定义。
• Synthesis of Photochromic Heterocyclic-Fused Naphthopyrans. Tuning the Color and Fading Speed
  作者：Vânia Graça、Céu M Sousa、Paulo J Coelho

  DOI：10.1246/bcsj.20230057

  日期：2023.7.15

  New photochromic 3-thienyl-3H-naphtho[1,2-b]pyrans fused to lactone and indole rings were efficiently prepared using a one-pot acid-catalyzed reaction, at room temperature, as the key step. These colorless photoswitches acquire intense red/brown shades under UV light and return spontaneously to the colorless state in the dark. The combination of the 3 heterocyclic rings assures a broad and intense absorption in the visible region and it allows a full switch between the two states in less than 1 min, at room temperature.

  摘要 以室温下的单锅酸催化反应为关键步骤，高效地制备了与内酯和吲哚环融合的新型光致变色 3-噻吩基-3H-萘并[1,2-b]吡喃。这些无色光开关在紫外光下会呈现强烈的红色/棕色，在黑暗中会自发恢复到无色状态。3 个杂环的组合确保了它们在可见光区域具有广泛而强烈的吸收，并能在室温下不到 1 分钟的时间内实现两种状态的完全切换。
• INTENSE COLOURING PHOTOCHROMIC 2H-NAPHTHO[1,2-b] PYRANS AND HETEROCYCLIC PYRANS
  申请人：JAMES ROBINSON LIMITED

  公开号：EP0975619B1

  公开（公告）日：2007-01-03
• NEUTRAL COLOURING PHOTOCHROMIC 2$i(H)-NAPHTHO 1,2-$i(b)]PYRANS AND HETEROCYCLIC PYRANS
  申请人：JAMES ROBINSON LIMITED

  公开号：EP0971914A2

  公开（公告）日：2000-01-19