(-)-(1R,2S,5R)-8-环己基薄荷醇 | 104197-80-0

• 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
• 中文名称: (-)-(1R,2S,5R)-8-环己基薄荷醇
• 英文名称: (-)-(1R,2S,5R)-8-Cyclohexylmenthol
• CAS: 104197-80-0
• 化学式: C₁₆H₃₀O
• 分子量: 238.414
• InChiKey: FUUWSAOLKVCORN-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (-)-(1R,2S,5R)-8-环己基薄荷醇 在 吡啶 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 4-Oxo-piperidine-1-carboxylic acid (1R,2S,5R)-2-(1-cyclohexyl-1-methyl-ethyl)-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  Lewis acid-promoted asymmetric conjugate allylation of N-acyl-2,3-dihydro-4-pyridones induced by intramolecular π interactions

  摘要：

  Lewis acid-promoted conjugate addition reaction of an allylsilane to a series of the chiral 8-arylmenthol-derived N-acyl-2,3-dihydro-4-pyridones leads to the 2-allyl-4-piperidones with moderate to high levels of asymmetric induction, indicating restacking contribution to chirality control. This methodology was applied to the asymmetric synthesis of (-)-N-methylconiine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02129-6
• 作为产物：
  描述：

  (-)-8-苯基薄荷醇 在 Rh on carbon 氢气 作用下， 生成 (-)-(1R,2S,5R)-8-环己基薄荷醇
  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

• Enantioselective Bromination of Silyl Enol Ethers with Chiral Pentacarboxycyclopentadienyl Bromide
  作者：Pingfan Li、Guo Liu

  DOI：10.1055/a-2088-9219

  日期：2023.12

  Chiral pentacarboxycyclopentadienyl bromide reagents were synthesized to accomplish enantioselective bromination of silyl enol ethers to give corresponding α-bromoketone products in good yields and up to 77% ee. A catalytic version of this reaction was also demonstrated through the combination of Lewis acid activators and diethyl 2,2-dibromomalonate as stoichiometric achiral bromine source.

  合成了手性五羧基环戊二烯基溴化试剂，以实现甲硅烷基烯醇醚的对映选择性溴化，以良好的产率和高达 77% ee 得到相应的 α-溴酮产物。该反应的催化形式也通过路易斯酸活化剂和 2,2-二溴丙二酸二乙酯的组合作为化学计量的非手性溴源得到证明。