(E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one | 111391-35-6

• 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: (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 4-benzyloxy-2'-hydroxy-4'-methoxy-trans-chalcone；4-Benzyloxy-2'-hydroxy-4'-methoxy-trans-chalkon；2'-Hydroxy-4'-methoxy-4-benzyloxy-trans-chalkon；(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 111391-35-6
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: TUVXMVKMWGXOBT-NTEUORMPSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  585.2±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 在 盐酸 、 sodium hydroxide 、 双氧水 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 19.25h， 生成 4H-1-苯并吡喃-4-酮,2-(4-羟基苯基)-3,7-二甲氧基-
  参考文献：
  名称：

  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

  摘要：

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.

  DOI：

  10.1021/jm00106a039
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 丹皮酚 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以50%的产率得到(E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型异寡糖原蛋白衍生物的合成和评价，可作为淀粉样β聚集和5-脂氧合酶的潜在双重抑制剂

  摘要：

  合成了一系列新的异源寡糖原蛋白（ISL）衍生物，并将其评估为β-淀粉样蛋白（Aβ）聚集和5-脂氧合酶（5-LO）的双重抑制剂。发现所有这些合成化合物均能有效抑制Aβ（1-42）聚集，其IC 50值为2.2±1.5μM至23.8±2.0μM。这些衍生物还显示出对5-LO的抑制活性，其IC 50值范围为6.1±0.1μM至35.9±0.3μM。研究了它们的结构-活性关系（SAR）和抑制机理。这项研究为进一步开发ISL衍生物作为阿尔茨海默氏病（AD）的多功能药物提供了潜在的重要信息。

  DOI：

  10.1016/j.ejmech.2013.05.015

文献信息

• Mahal et al., Journal of the Chemical Society, 1935, p. 866
  作者：Mahal et al.

  DOI：——

  日期：——
• Tatsuta, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1942, vol. 63, p. 935,941
  作者：Tatsuta

  DOI：——

  日期：——
• A highly efficient and environmentally benign synthesis of 6,8-dibromoflavones, 8-bromoflavones, 5,7-dibromoaurones and 7-bromoaurones
  作者：Abu T. Khan、Papori Goswami

  DOI：10.1016/j.tetlet.2005.05.102

  日期：2005.7

  Various ring substituted 6,8-dibromoflavones (3a-e) as well as 8-bromoflavolics (3f-j) can be synthesized easily from the corresponding 2'-hydroxychalcones (1a-j) in good yields and in two steps under environmentally benign reaction conditions. This can be achieved by bromination with concomitant cyclization by using a combination of vanadium pentoxide, hydrogen peroxide and ammonium bromide in dichloromethane-water at 0-5 degrees C, followed by dehydrobromination of the brominated products 2a-j using 0.2 M ethanolic KOH Solution at ice-bath temperature. On the other hand, various 5,7-dibromoaurones and 7-bromoaurone derivatives 6a-c can be obtained, exclusively, from the corresponding 2'-acetoxychalcones (4a-c) in good yields and in two steps by turing the reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.
• Fujise; Tatsuta, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1942, vol. 63, p. 932,933
  作者：Fujise、Tatsuta

  DOI：——

  日期：——
• DE, MEYER NADINE;HAEMERS, ACHIEL;MISHRA, LALLAN;PANDEY, HRISHI-KESH;PIETE+, J. MED. CHEM., 34,(1991) N, C. 736-746
  作者：DE, MEYER NADINE、HAEMERS, ACHIEL、MISHRA, LALLAN、PANDEY, HRISHI-KESH、PIETE+

  DOI：——

  日期：——