1-[2,4-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-prenylphenyl]-3-(4-pivaloyloxy-3-methoxyphenyl)-1,3-propanedione | 1030601-57-0

• 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: 1-[2,4-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-prenylphenyl]-3-(4-pivaloyloxy-3-methoxyphenyl)-1,3-propanedione
• 英文别名: [4-[3-[2,4-Bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxy-3-(3-methylbut-2-enyl)phenyl]-3-oxopropanoyl]-2-methoxyphenyl] 2,2-dimethylpropanoate
• CAS: 1030601-57-0
• 化学式: C₃₈H₅₈O₈Si₂
• 分子量: 699.045
• InChiKey: AGSIDWDOCPCAJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.08
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[2,4-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-prenylphenyl]-3-(4-pivaloyloxy-3-methoxyphenyl)-1,3-propanedione 在 三甲基氯硅烷 、 copper dichloride 、 水 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以60%的产率得到7-O-tert-butyldimethylsilyl-4'-O-pivaloylcannflavin B
  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：

  2-acetyl-3,5-bis((tert-butyldimethylsilyl)oxy)-4-(3-methylbut-2-en-1-yl)phenyl 3-methoxy-4-(pivaloyloxy)benzoate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以500 mg的产率得到1-[2,4-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-prenylphenyl]-3-(4-pivaloyloxy-3-methoxyphenyl)-1,3-propanedione
  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.