4',6-Dimethyl-3-hydroxyflavone | 78396-37-9

• 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: 4',6-Dimethyl-3-hydroxyflavone
• 英文别名: 4H-1-Benzopyran-4-one, 3-hydroxy-6-methyl-2-(4-methylphenyl)-；3-hydroxy-6-methyl-2-(4-methylphenyl)chromen-4-one
• CAS: 78396-37-9
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: OUNDHKZAGANSPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4',6-Dimethyl-3-hydroxyflavone 以 甲醇 为溶剂， 以3%的产率得到6-methyl-3-p-tolyl-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Photochemistry of flavonoids. III. Photorearrangement of flavonols.

  摘要：

  在甲醇中辐照黄酮醇（1）可得到 3-芳邻苯酞（3），后者通过二酮（4）形成。金属离子（Cu2+、Ni2+、Fe3+、Co2+ 和 Be2+）抑制了这种重排。

  DOI：

  10.1248/cpb.29.894
• 作为产物：
  描述：

  1-(2-羟基-5-甲基苯基)-3-(4-甲基苯基)丙烷-1,3-二酮 在 硫酸 、 二甲基二环氧乙烷 、 溶剂黄146 作用下， 以 氘代氯仿 、 二氯甲烷 、 丙酮 为溶剂， 反应 46.0h， 生成 4',6-Dimethyl-3-hydroxyflavone
  参考文献：
  名称：

  Epoxidation of flavones by dimethyldioxirane

  摘要：

  The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported. These labile epoxides were isolated and completely characterized by UV, IR, H-1 and C-13 NMR, MS, and C, H analyses. Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n. Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f as a mixture of cis and trans isomers.

  DOI：

  10.1021/jo00026a020

文献信息

• Absorption and Fluorescent Studies of 3-Hydroxychromones
  作者：Radhika Khanna、Ramesh Kumar、Aarti Dalal、Ramesh C. Kamboj

  DOI：10.1007/s10895-015-1623-0

  日期：2015.9

  The synthesis and spectral studies of variously substituted 3-hydroxychromones have been carried out. A key relationship between the structural motif of synthesized 3-hydroxychromones (3-HCs) and their fluorescent properties was found. The chromones substituted with electron-donating group at 4′-position expressed the red shift of the N* and T* band and also exhibited the increased fluorescent intensity ratio while the chromones with electron-withdrawing group showed the blue shift of the N* and T* band. Therefore, these 3-HCs may behave as the possible fluorescent probes.

  已经进行了各种取代的3-羟基色酮的合成和光谱研究。发现了合成的 3-羟基色酮 (3-HC) 的结构基序与其荧光特性之间的关键关系。 4'位被给电子基团取代的色酮表现出N*和T*带的红移，并且荧光强度比增加，而带有吸电子基团的色酮则表现出N*和T*带的蓝移。 T*带。因此，这些 3-HC 可能充当可能的荧光探针。
• Bhandari; Sodani; Sharma, Journal of the Indian Chemical Society, 2006, vol. 83, # 11, p. 1113 - 1117
  作者：Bhandari、Sodani、Sharma、Chundawat, Jagveer S.、Dulawat, Shiv S.、Verma

  DOI：——

  日期：——
• Epoxidation of flavones by dimethyldioxirane
  作者：Waldemar Adam、Dieter Golsch、Lazaros Hadjiarapoglou、Tamas Patonay

  DOI：10.1021/jo00026a020

  日期：1991.12

  The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported. These labile epoxides were isolated and completely characterized by UV, IR, H-1 and C-13 NMR, MS, and C, H analyses. Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n. Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f as a mixture of cis and trans isomers.
• Photochemistry of flavonoids. III. Photorearrangement of flavonols.
  作者：ICHIRO YOKOE、KYOKO HIGUCHI、YOSHIAKI SHIRATAKI、MANKI KOMATSU

  DOI：10.1248/cpb.29.894

  日期：——

  Irradiation of flavonols (1) in methanol gave 3-arylphthalides (3) which were formed via the diketones (4). Metal ions (Cu2+, Ni2+, Fe3+, Co2+ and Be2+) inhibited this rearrangement.

  在甲醇中辐照黄酮醇（1）可得到 3-芳邻苯酞（3），后者通过二酮（4）形成。金属离子（Cu2+、Ni2+、Fe3+、Co2+ 和 Be2+）抑制了这种重排。