(+/-)-(E)-1-<4-<(tert-Butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-3-methyl-7-phenyl-6-hepten-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (+/-)-(E)-1-<4-<(tert-Butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-3-methyl-7-phenyl-6-hepten-1-ol
• 英文别名: (E)-1-[4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethylphenyl]-3-methyl-7-phenylhept-6-en-1-ol
• 化学式: C₂₈H₄₂O₂Si
• 分子量: 438.726
• InChiKey: ARRMRUXPLCMXSU-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.24
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(E)-1-<4-<(tert-Butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-3-methyl-7-phenyl-6-hepten-1-ol 在 四丁基氟化铵 、 四氯化钛 作用下， 生成 (+/-)-(3S^*,4S^*,9S^*,9aS^*)-7-Hydroxy-9-phenyl-3,6,8-trimethyl-1,2,3,4,4a,9,9a-heptahydrofluorene
  参考文献：
  名称：

  Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes

  摘要：

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.

  DOI：

  10.1021/jo00071a024
• 作为产物：
  描述：

  (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene 在 草酰氯 、 四丁基氟化铵 、 叔丁基锂 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 16.33h， 生成 (+/-)-(E)-1-<4-<(tert-Butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-3-methyl-7-phenyl-6-hepten-1-ol
  参考文献：
  名称：

  Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes

  摘要：

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.

  DOI：

  10.1021/jo00071a024

文献信息

• Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes
  作者：Steven R. Angle、Rogelio P. Frutos

  DOI：10.1021/jo00071a024

  日期：1993.9

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.