2,4-O-bis(tert-butyldimethylsilyl)-3-prenylphloracetophenone | 1030601-54-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-O-bis(tert-butyldimethylsilyl)-3-prenylphloracetophenone
• 英文别名: 1-[2,4-Bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxy-3-(3-methylbut-2-enyl)phenyl]ethanone
• CAS: 1030601-54-7
• 化学式: C₂₅H₄₄O₄Si₂
• 分子量: 464.793
• InChiKey: QINJSTLUYMPGOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  492.1±45.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  4-O-pivaloylvanilloyl chloride 、 2,4-O-bis(tert-butyldimethylsilyl)-3-prenylphloracetophenone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.7h， 生成 2-acetyl-3,5-bis((tert-butyldimethylsilyl)oxy)-4-(3-methylbut-2-en-1-yl)phenyl 3-methoxy-4-(pivaloyloxy)benzoate
  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：

  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

文献信息

• A Multicomponent Carba-Betti Strategy to Alkylidene Heterodimers - Total Synthesis and Structure-Activity Relationships of Arzanol
  作者：Alberto Minassi、Lavinia Cicione、Andreas Koeberle、Julia Bauer、Stefan Laufer、Oliver Werz、Giovanni Appendino

  DOI：10.1002/ejoc.201101193

  日期：2012.2

  Using the synthesis of the heterodimeric phloroglucinyl pyrone arzanol as a benchmark reaction, a carba-version of the Betti multicomponent reaction has been developed. Capitalizing on the fluorous activation of the phenolic component and the use of iminium ions as bivalent and "transmissive" aldehyde equivalents, the reaction has been used to colonize a biologically privileged but previously inaccessible

  使用异二聚体间苯二酚吡喃酮 arzanol 的合成作为基准反应，已经开发了 Betti 多组分反应的 carba 版本。利用酚类成分的氟活化和亚胺离子作为二价和“传递性”醛等价物的使用，该反应已被用于殖民一个生物学上特权但以前无法进入的化学空间区域，并研究 arzanol 的结构 - 活性关系针对一系列促炎靶点（mPGES-1、5-LO）。
• 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.