[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(5-hydroxy-6,7-dimethoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl]methyl acetate | 13020-20-7

• 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: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(5-hydroxy-6,7-dimethoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl]methyl acetate
• CAS: 13020-20-7
• 化学式: C₃₁H₃₂O₁₅
• 分子量: 644.586
• InChiKey: UDLDEWXNAVRUQR-IEDCVRSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(5-hydroxy-6,7-dimethoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl]methyl acetate 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以66%的产率得到滨蓟黄甙
  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：

  6--2,3,4-trimethoxy-acetophenon 在 吡啶 、 硫酸 、 palladium on activated charcoal 、 苄基三乙基氯化铵 、 氢气 、 三溴化硼 、 溶剂黄146 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 12.0h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(5-hydroxy-6,7-dimethoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl]methyl acetate
  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