methyl 4-hydroxy-1-methoxy-2-naphthoate | 131237-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-hydroxy-1-methoxy-2-naphthoate
• 英文别名: Methyl 4-hydroxy-1-methoxynaphthalene-2-carboxylate
• CAS: 131237-67-7
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: SCTHZZPSMURSQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-bis(2-methoxyphenyl)-3-phenylprop-2-yn-1-ol 、 methyl 4-hydroxy-1-methoxy-2-naphthoate 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以72%的产率得到methyl 6-methoxy-2,2-bis(2-methoxyphenyl)-4-phenylnaphtho[1,2-b]pyran-5-carboxylate
  参考文献：
  名称：

  增强光致变色熔融萘并吡喃的颜色强度

  摘要：

  描述了多环光致变色稠合萘并吡喃的简短合成。与普通的光致变色萘并吡喃不同，在紫外线辐射下会产生一种有色的光异构体，该异构体在黑暗中返回到无色状态，比未融合的萘并吡喃母体快得多。掺有该染料的未着色聚合物薄膜可在30秒钟内用紫外线激活，并在黑暗中1分钟内失去90％的着色。使用这种新的光致变色熔融萘并吡喃，在有色物质的热褪色中观察到的残留色度分散在聚合物基质中，残留色度降低到5％。

  DOI：

  10.1016/j.dyepig.2019.05.013
• 作为产物：
  描述：

  methyl 1-methoxy-4-(propionyloxy)-2-naphthoate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以1.7 g的产率得到methyl 4-hydroxy-1-methoxy-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

• Joining High Coloration and Fast Color Fading with Photochromic Fused-Naphthopyrans
  作者：Céu M. Sousa、Paulo J. Coelho

  DOI：10.1002/ejoc.201901814

  日期：2020.2.28

  An easy synthesis of photochromic naphthopyrans with a fused lactone ring is described. UV irradiation of these uncolored compounds, in solution or dispersed in polymeric materials, provide a single photoisomer with an intense orange coloration that returns completely to the initial uncolored state in less than 2 min at room temperature.

  描述了具有稠合内酯环的光致变色萘并吡喃的容易合成。这些未着色的化合物在溶液中或分散在聚合物材料中的紫外线照射提供了一种具有强烈橙色的光异构体，在室温下不到2分钟即可完全恢复为初始未着色状态。
• Studies dealing with the excited-state behavior of substituted 8-oxabicyclo[3.2.1]oct-6-en-2-ones
  作者：Albert Padwa、Lin Zhi、Glen E. Fryxell

  DOI：10.1021/jo00003a032

  日期：1991.2

  A series of 8-oxabicyclo [3.2.1]oct-6-en-2-ones was prepared by the rhodium(II)-catalyzed cyclization-cycloaddition reaction of alpha-diazopentanedione with various alkynes. The photochemical behavior of these oxabicyclic enones was investigated. Both direct and sensitized photolysis cleanly results in a 1,3-acyl shift. A slower, secondary photoprocess involving intramolecular hydrogen atom transfer and intramolecular cycloaddition of the resulting ketene was also uncovered. The photobehavior of the closely related 9-oxabenzocycloheptene system was also examined. The initially formed 1,3-sigmatropic rearranged product was found to undergo a novel 1,4-methoxyl migration on extended photolysis. The photochemistry of the homologous 7-oxabicyclo[2.2.1]hepten-2-one was studied. The results obtained can be interpreted in terms of an initial Norrish type I cleavage. The resulting diradical either couples to give the 1,3-acyl shift product or undergoes bond fragmentation, giving products derived from a stepwise retro-Diels-Alder reaction.
• PADWA, ALBERT;ZHI, LIN;FRYXELL, GLEN E., J. ORG. CHEM., 56,(1991) N, C. 1077-1083
  作者：PADWA, ALBERT、ZHI, LIN、FRYXELL, GLEN E.

  DOI：——

  日期：——
• MAKHLOUF, M. A.;RICKBORN, B., J. ORG. CHEM., 1981, 46, N 13, 2734-2739
  作者：MAKHLOUF, M. A.、RICKBORN, B.

  DOI：——

  日期：——
• 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。