trimethyl(4,6,7,9a-tetrahydro-6,6,9a-trimethylnaphtho<1,2-b>furan-2-yl)silane | 144492-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trimethyl(4,6,7,9a-tetrahydro-6,6,9a-trimethylnaphtho<1,2-b>furan-2-yl)silane
• CAS: 144492-79-5
• 化学式: C₁₈H₂₆OSi
• 分子量: 286.489
• InChiKey: FFDQFKXNQHWFPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trimethyl(4,6,7,9a-tetrahydro-6,6,9a-trimethylnaphtho<1,2-b>furan-2-yl)silane 在 palladium on activated charcoal 氢气 、 乙酸乙酯 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以68%的产率得到trimethyl(trans-4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethylnaphtho<1,2-b>furan-2-yl)silane
  参考文献：
  名称：

  Enantioselective construction of natural (+)-pallescensin A. A sigmatropic pathway to furanosesquiterpenes.

  摘要：

  Addition of the cerium reagent derived from 3-lithiofuran and anhydroUS CeCl3 to optically pure bicyclic ketone 2 affords alcohol 4 selectively. Anionic oxy-Cope rearrangement of 4 in hot diglyme results in conversion to keto aldehyde 6, a consequence of beta-elimination following upon the [3,3]sigmatropic event. Advantage was then taken of chemoselective acetalization and unidirectional introduction of an enone double bond. Regio- and stereoselective epoxidation of 8 was a prelude to formation of the furan ring by BF3.etherate-promoted cyclization. Once the carbonyl group was reduced with alane, catalytic hydrogenation in the presence of diethylamine gave the title compound. An alternative scheme involving silylation of the furan ring as a protective maneuver, while entirely workable, was both less direct and less efficient.

  DOI：

  10.1021/jo00052a026
• 作为产物：
  描述：

  三甲基氯硅烷 、 axinellin-B 在 正丁基锂 、 1-叠氮基乙烷 作用下， 生成 trimethyl(4,6,7,9a-tetrahydro-6,6,9a-trimethylnaphtho<1,2-b>furan-2-yl)silane
  参考文献：
  名称：

  Enantioselective construction of natural (+)-pallescensin A. A sigmatropic pathway to furanosesquiterpenes.

  摘要：

  Addition of the cerium reagent derived from 3-lithiofuran and anhydroUS CeCl3 to optically pure bicyclic ketone 2 affords alcohol 4 selectively. Anionic oxy-Cope rearrangement of 4 in hot diglyme results in conversion to keto aldehyde 6, a consequence of beta-elimination following upon the [3,3]sigmatropic event. Advantage was then taken of chemoselective acetalization and unidirectional introduction of an enone double bond. Regio- and stereoselective epoxidation of 8 was a prelude to formation of the furan ring by BF3.etherate-promoted cyclization. Once the carbonyl group was reduced with alane, catalytic hydrogenation in the presence of diethylamine gave the title compound. An alternative scheme involving silylation of the furan ring as a protective maneuver, while entirely workable, was both less direct and less efficient.

  DOI：

  10.1021/jo00052a026