6-O-prenyl-2,4-O-bis(tert-butyldimethylsilyl)phloracetophenone | 1030601-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-prenyl-2,4-O-bis(tert-butyldimethylsilyl)phloracetophenone
• 英文别名: Bis-OTBS-6-[(3-methyl-2-buten-1-yl)oxy]phenyl]ethanone；1-[2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-(3-methylbut-2-enoxy)phenyl]ethanone
• CAS: 1030601-61-6
• 化学式: C₂₅H₄₄O₄Si₂
• 分子量: 464.793
• InChiKey: UIRQBPFQIXNMJE-UHFFFAOYSA-N

物化性质

• 沸点：
  475.3±45.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-O-prenyl-2,4-O-bis(tert-butyldimethylsilyl)phloracetophenone 在 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以81%的产率得到2,4-O-bis(tert-butyldimethylsilyl)-3-prenylphloracetophenone
  参考文献：
  名称：

  A Regiodivergent Synthesis of Ring A C-Prenylflavones

  摘要：

  Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.

  DOI：

  10.1021/ol800665w
• 作为产物：
  描述：

  4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone 、 异戊烯醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到6-O-prenyl-2,4-O-bis(tert-butyldimethylsilyl)phloracetophenone
  参考文献：
  名称：

  A Regiodivergent Synthesis of Ring A C-Prenylflavones

  摘要：

  Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.

  DOI：

  10.1021/ol800665w

文献信息

• A Regiodivergent Synthesis of Ring A C-Prenylflavones
  作者：Alberto Minassi、Anna Giana、Abdellah Ech-Chahad、Giovanni Appendino

  DOI：10.1021/ol800665w

  日期：2008.6.5

  Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.