(Z)-3(2-hydroxyphenyl)-1(4-methoxyphenyl)-3-oxo-prop-1-en-1-ol | 148788-26-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-3(2-hydroxyphenyl)-1(4-methoxyphenyl)-3-oxo-prop-1-en-1-ol
• 英文别名: (z)-3(2-Hydroxyphenyl)-1-(4-methoxyphenyl)-3-oxo-prop-1-en-1-ol；(Z)-3-hydroxy-1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 148788-26-5
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: MRGRXFAIKMUAOA-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (Z)-3(2-hydroxyphenyl)-1(4-methoxyphenyl)-3-oxo-prop-1-en-1-ol 在 哌啶 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 11.0h， 生成 3-(4''-methoxybenzoyl)-3',4',5'-trimethoxyflavone
  参考文献：
  名称：

  Synthesis and anti-tubulin evaluation of chromone-based analogues of combretastatins

  摘要：

  Twenty new hybrid compounds with both combretastatin and flavone moieties were synthesized. These derivatives are classified according to the position of the trimethoxyphenyl ring at C-2 or C-3 of the chromone and presence or absence of a carbonyl as a linker between C-3 and the aryl ring. Most of these compounds were prepared from hesperidin or naringin, two natural and abundant Citrus flavonoids. Seven of these combretastatin analogues revealed anti-tubulin activity but in a medium range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.024
• 作为产物：
  描述：

  2-乙酰基苯基对茴香酸酯 在 氢氧化钾 作用下， 反应 3.0h， 以925 mg的产率得到(Z)-3(2-hydroxyphenyl)-1(4-methoxyphenyl)-3-oxo-prop-1-en-1-ol
  参考文献：
  名称：

  Synthesis and anti-tubulin evaluation of chromone-based analogues of combretastatins

  摘要：

  Twenty new hybrid compounds with both combretastatin and flavone moieties were synthesized. These derivatives are classified according to the position of the trimethoxyphenyl ring at C-2 or C-3 of the chromone and presence or absence of a carbonyl as a linker between C-3 and the aryl ring. Most of these compounds were prepared from hesperidin or naringin, two natural and abundant Citrus flavonoids. Seven of these combretastatin analogues revealed anti-tubulin activity but in a medium range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.024

文献信息

• New Syntheses of 3-Aroylflavone Derivatives; Knoevenagel Condensation and Oxidation versus One-Pot Synthesis
  作者：Diana Pinto、Artur Silva、Patrícia Vaz、Djenisa Rocha、José Cavaleiro

  DOI：10.1055/s-0032-1317159

  日期：——

  syntheses of 3-aroylflavones have been established. In the first synthesis the use of microwave irradiation led to an improvement in the yields of both the Knoevenagel condensation of β-diketones with aldehydes to afford 3-aroylflavanones and of their oxidation to 3-aroylflavones. In the second and more general synthesis, a novel and efficient procedure for 3-aroylflavones involves a one-pot reaction between

  已经建立了 3-芳酰基黄酮的两种合成方法。在第一次合成中，微波辐射的使用导致 β-二酮与醛的 Knoevenagel 缩合得到 3-芳酰基黄烷酮以及它们氧化为 3-芳酰基黄酮的产率的提高。在第二个和更一般的合成中，3-芳酰基黄酮的新型有效程序涉及在双（三甲基甲硅烷基）氨基锂存在下 2'-羟基苯乙酮和芳酰氯之间的一锅反应。
• Antus, Sandor; Baitz-Gacs, Eszter; Boross, Ferenc, Liebigs Annalen der Chemie, 1980, # 8, p. 1271 - 1282
  作者：Antus, Sandor、Baitz-Gacs, Eszter、Boross, Ferenc、Nogradi, Mihaly、Solyom, Aniko

  DOI：——

  日期：——