2-(4-Methoxy-phenyl)-2H-chromen-2-ol | 99618-41-4

• 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: 2-(4-Methoxy-phenyl)-2H-chromen-2-ol
• 英文别名: 2-(4-Methoxyphenyl)chromen-2-ol；2-(4-methoxyphenyl)chromen-2-ol
• CAS: 99618-41-4
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: ALNYTORPHVVAIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Methoxy-phenyl)-2H-chromen-2-ol 在 水 作用下， 生成 (Z)-3-(2-Hydroxy-phenyl)-1-(4-methoxy-phenyl)-propenone
  参考文献：
  名称：

  Hydration of the flavylium ion

  摘要：

  DOI：

  10.1021/ja00538a024
• 作为产物：
  描述：

  (Z)-3-(2-Hydroxy-phenyl)-1-(4-methoxy-phenyl)-propenone 在 氢气 作用下， 以 水 为溶剂， 生成 2-(4-Methoxy-phenyl)-2H-chromen-2-ol
  参考文献：
  名称：

  Hydration of the flavylium ion. 3. The effect of 3-alkyl substitution

  摘要：

  DOI：

  10.1021/jo00350a046

文献信息

• Hydration of the flavylium ion
  作者：Robert A. McClelland、Sherrin Gedge

  DOI：10.1021/ja00538a024

  日期：1980.8
• Photochromism of 4‘-Methoxyflavylium Perchlorate. A “Write−Lock−Read−Unlock−Erase” Molecular Switching System
  作者：Fernando Pina、Maria João Melo、Mauro Maestri、Roberto Ballardini、Vincenzo Balzani

  DOI：10.1021/ja9704646

  日期：1997.6.1

  In aqueous solution (2 < pH < 8) the thermodynamically stable form of the 4'-methoxyflavylium ion (AH(+)) is its hydrated derivative trans-4'-methoxychalcone, C-t. The C-t compound shows a broad absorption band with lambda(max) = 350 nm. In acid medium, irradiation of C-t with near-UV light causes strong spectral changes with five isosbestic points and appearance of a very intense band in the visible region with maximum at 435 nm, corresponding to the AH(+) form. :It has been shown that irradiation of C-t causes a trans --> cis photoisomerization reaction (Phi = 0.04 at lambda(exc) = 365 nm), which is followed by 100% conversion of the cis-chalcone form (C-c) to the AH(+) ion. The AH(+) ion is photochemically inactive and thermally inert in acid medium (half-life of the back conversion at 25 degrees C in the dark is 815 days at pH 1.0 and 20 h at pH 4.3, respectively). At high temperature (>50 degrees C) and/or pH greater than or equal to 3, however, AH(+) can be quantitatively converted back to C-t (half-life of 15 min at pH 4.0 and 60 degrees C). Owing to this unique behavior, this represents a novel molecular system in which the color can be controlled by light and changes in temperature and/or pH. The ability to photochemically convert the stable and colorless C-t form to the kinetically inert and colored AH(+) form, and the possibility to reconvert AH(+) to C-t at high temperature or by a pH jump make the system well-suited as the basis for an optical memory device with multiple storage and nondestructive readout capacity through a write-lock-read-unlock-erase cycle.
• Hydration of the flavylium ion. 3. The effect of 3-alkyl substitution
  作者：David B. Devine、Robert A. McClelland

  DOI：10.1021/jo00350a046

  日期：1985.12