α-(p-Benzyloxy-benzoyl)-6-hydroxy-2,3,4-trimethoxy-acetophenon | 95868-61-4

• 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: α-(p-Benzyloxy-benzoyl)-6-hydroxy-2,3,4-trimethoxy-acetophenon
• 英文别名: 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)-3-(4-phenylmethoxyphenyl)propane-1,3-dione
• CAS: 95868-61-4
• 化学式: C₂₅H₂₄O₇
• 分子量: 436.461
• InChiKey: ZAWALHGAMAHGOK-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C(Solv: ethanol (64-17-5))
• 沸点：
  652.2±55.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  α-(p-Benzyloxy-benzoyl)-6-hydroxy-2,3,4-trimethoxy-acetophenon 在 硫酸 、 palladium on activated charcoal 、 氢气 、 三溴化硼 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 蓟黄素
  参考文献：
  名称：

  Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes

  摘要：

  A straightforward procedure leading to the flavone cirsimaritin and its 4'-O-beta-D-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.034
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 吡啶 、 三氟化硼乙醚 、 sodium acetate 、 溶剂黄146 、 potassium hydroxide 作用下， 反应 24.0h， 生成 α-(p-Benzyloxy-benzoyl)-6-hydroxy-2,3,4-trimethoxy-acetophenon
  参考文献：
  名称：

  Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes

  摘要：

  A straightforward procedure leading to the flavone cirsimaritin and its 4'-O-beta-D-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.034

文献信息

• Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes
  作者：Christophe O. Soulage、Lucie Grand、Alain Géloën、Stéphane Chambert

  DOI：10.1016/j.tetlet.2011.11.034

  日期：2012.2

  A straightforward procedure leading to the flavone cirsimaritin and its 4'-O-beta-D-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity. (C) 2011 Elsevier Ltd. All rights reserved.