(-)-(1S,2S,3S)-exo-3-Benzyl-exo-2-isoborneol | 148219-19-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-(1S,2S,3S)-exo-3-Benzyl-exo-2-isoborneol
• 英文别名: (+)-cis-3-Benzylborneol
• CAS: 148219-19-6
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: GADSJJYOMMDNRG-QBYUYEEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (-)-(1S,2S,3S)-exo-3-Benzyl-exo-2-isoborneol 在 Rh on carbon 吡啶 、 氢气 作用下， 生成 (-)-Tetrakis<(1S,2S,3S)-exo-3-(cyclohexylmethyl)-exo-2-isobornyl>1,2,4,5-benzenetetracarboxylate
  参考文献：
  名称：

  Highly enantiodifferentiating photoisomerization of cyclooctene by congested and/or triplex-forming chiral sensitizers

  摘要：

  In an effort to generate photoproducts with higher optical purities (op), two novel strategies, i.e., intra/intermolecular triplex formation and increased steric hindrance, have been employed in the enantiodifferentiating Z --> E photoisomerization of cyclooctene (1) sensitized by optically active (ar)alkyl benzene(poly)carboxylates 2-5 at temperatures ranging from 25 to -90-degrees-C. The newly synthesized benzenepolycarboxylates, possessing extremely bulky and/or electron-donating (ar)-alkyl groups, gave products with the highest op's ever reported for the enantiodifferentiating photosensitizations, not only at low temperatures (up to 64% op at -89-degrees-C) but also at ambient temperature (50% op). Both strategies to fix the sensitizer conformation and to induce more dynamic conformational changes in the exciplex/triplex intermediate are shown to function well and to give very high op's. The temperature-dependence studies also demonstrate that the temperature switching of the product chirality is not an extraordinary but rather a general phenomenon, which is attributed to the significant contribution of the entropy factor in the enantiodifferentiating process, caused by the dynamic structural change in the excited complex.

  DOI：

  10.1021/jo00057a009

文献信息

• Totalsynthese von natülichem α-Tocopherol. 5. Mitteilung. Asymmetrische Alkylierung und asymmetrische Epoxidierung als Methoden zur Einführung der (<i>R</i>)-Konfiguration an C(2) des Chroman-Systems
  作者：Josef Hübscher、Richard Barrier

  DOI：10.1002/hlca.19900730431

  日期：1990.6.20

  Total Synthesis of Naturally Occurring α-Tocopherol. Asymmetric Alkylation and Asymmetric Epoxidation as Means to Introduce (R)-Configuration at C(2) of the Chroman Moiety

  天然存在的α-生育酚的全合成。不对称的烷基化和不对称的环氧化作为引入（R）-配置在色度部分C（2）的手段