(1S,3R)-6-tert-butyldimethylsilyloxy-1,3-ethano-1-methyl-3,4-dihydro-1H-isochromene | 1092951-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1S,3R)-6-tert-butyldimethylsilyloxy-1,3-ethano-1-methyl-3,4-dihydro-1H-isochromene
• 英文别名: tert-butyl-dimethyl-[[(1S,9R)-1-methyl-12-oxatricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-5-yl]oxy]silane
• CAS: 1092951-39-7
• 化学式: C₁₈H₂₈O₂Si
• 分子量: 304.505
• InChiKey: FQUFDVRMPSBRMI-KDOFPFPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R)-6-tert-butyldimethylsilyloxy-1,3-ethano-1-methyl-3,4-dihydro-1H-isochromene 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以96%的产率得到(+/-)-bruguierol A
  参考文献：
  名称：

  An Expeditious Synthesis of Bruguierol A

  摘要：

  A very simple strategy for the construction of 2,3-benzofused 8-oxabicyclo[3.2.1]octane derivatives is reported. This new process is based on a platinum-catalyzed tandem intramolecular hydroalkoxylation-hydroarylation reaction of aryl-substituted pentynol derivatives. This reaction has been applied in the key step of the total synthesis of bruguierol A, allowing the synthesis of this natural product in a very straightforward manner.

  DOI：

  10.1021/jo8021204
• 作为产物：
  描述：

  (R)-1-[3-(tert-butyldimethylsilyloxy)phenyl]hex-5-yn-2-ol 在 氯化铂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到(1S,3R)-6-tert-butyldimethylsilyloxy-1,3-ethano-1-methyl-3,4-dihydro-1H-isochromene
  参考文献：
  名称：

  An Expeditious Synthesis of Bruguierol A

  摘要：

  A very simple strategy for the construction of 2,3-benzofused 8-oxabicyclo[3.2.1]octane derivatives is reported. This new process is based on a platinum-catalyzed tandem intramolecular hydroalkoxylation-hydroarylation reaction of aryl-substituted pentynol derivatives. This reaction has been applied in the key step of the total synthesis of bruguierol A, allowing the synthesis of this natural product in a very straightforward manner.

  DOI：

  10.1021/jo8021204

文献信息

• An Expeditious Synthesis of Bruguierol A
  作者：Francisco J. Fañanás、Amadeo Fernández、Deniz Çevic、Félix Rodríguez

  DOI：10.1021/jo8021204

  日期：2009.1.16

  A very simple strategy for the construction of 2,3-benzofused 8-oxabicyclo[3.2.1]octane derivatives is reported. This new process is based on a platinum-catalyzed tandem intramolecular hydroalkoxylation-hydroarylation reaction of aryl-substituted pentynol derivatives. This reaction has been applied in the key step of the total synthesis of bruguierol A, allowing the synthesis of this natural product in a very straightforward manner.