tert-butyldiphenyl((1RS,4aSR,10aRS)-1,4a,7-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yloxy)silane

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: tert-butyldiphenyl((1RS,4aSR,10aRS)-1,4a,7-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yloxy)silane
• 英文别名: [(1R,4aS,10aR)-1,4a,7-trimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]oxy-tert-butyl-diphenylsilane
• 化学式: C₃₃H₄₂OSi
• 分子量: 482.781
• InChiKey: GKWLOBPGXNLMSN-JORIVFIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 咪唑 、 sodium tetrahydroborate 、 18-冠醚-6 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.17h， 生成 tert-butyldiphenyl((1RS,4aSR,10aRS)-1,4a,7-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yloxy)silane
  参考文献：
  名称：

  Catalytic Diastereoselective Polycyclization of Homo(polyprenyl)arene Analogues Bearing Terminal Siloxyvinyl Groups

  摘要：

  Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.

  DOI：

  10.1021/ol062378t

文献信息

• Catalytic Diastereoselective Polycyclization of Homo(polyprenyl)arene Analogues Bearing Terminal Siloxyvinyl Groups
  作者：Muhammet Uyanik、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1021/ol062378t

  日期：2006.11.1

  Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.