(1R)-endo-2-methylfenchol | 137255-08-4

• 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: (1R)-endo-2-methylfenchol
• 英文别名: (1R,2R,4S)-1,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-ol
• CAS: 137255-08-4
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: AJVKAPQCJKEUSG-GDPRMGEGSA-N

物化性质

• 沸点：
  208.7±8.0 °C(predicted)
• 密度：
  0.968±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-endo-2-methylfenchol 在 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 生成 (1R,2R,4S)-1,2,3,3-tetramethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  On the stability and radical deoxygenation of tertairy xanthates.

  摘要：

  Xanthates of tertiary alcohols were isolated and properly characterized. Radical deoxygenation reactions under various conditions to the corresponding alkanes were successfully carried out. Comparative data of various initiatiors and hydrogen atom donors for xanthate deoxygenation are reported.

  DOI：

  10.1016/s0040-4039(00)73548-9
• 作为产物：
  描述：

  (1R,4S)-2-ethynyl-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 在 N-甲基吡咯烷酮 、 氢氧化钾 作用下， 反应 4.0h， 生成 (1R)-endo-2-methylfenchol
  参考文献：
  名称：

  土臭气味化合物-II乙基α-和β-苯酚的合成

  摘要：

  几个立体选择性路线都是乙基α-和β-fenchols和进行了讨论。将乙基锂直接添加到Fenchone中是最好的途径，而乙炔基α-和β-苯酚和的混合物的高度立体选择性逆乙炔化则可达到这一目的。

  DOI：

  10.1016/s0040-4039(00)94718-x

文献信息

• Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones:  Progress toward Defining an Optimum Chiral Auxiliary
  作者：Anthony J. Pearson、Alexander V. Gontcharov

  DOI：10.1021/jo971676o

  日期：1998.1.1

  the asymmetric synthesis of 5-substituted cyclohexenones via nucleophile addition to (alkoxyarene)chromium tricarbonyl complexes is described. Diastereoselectivity during the nucleophile addition step was achieved using alkoxy substituents derived from terpenoid substrates as chiral auxiliaries. Selectivities as high as 24:1 were obtained when 2-phenylisoborneol was used as the chiral auxiliary and

  描述了通过向（烷氧基芳烃）铬三羰基络合物加成亲核试剂，对5-取代的环己酮进行不对称合成的研究。使用衍生自萜类底物的烷氧基取代基作为手性助剂，可以实现亲核试剂加成步骤中的非对映选择性。当使用2-苯基异冰片醇作为手性助剂时，选择性高达24：1，而使用3,3-（亚乙基二氧基）异冰片醇则高达17：1。在将其转化成相应的环己烯醇后，主要产物的绝对立体化学由Mosher方法确定。对亲核体加成烷氧基甲苯络合物的温度依赖性的研究表明，热力学偏向邻位加成醚取代基。
• A Study of Cations Derived from exo-2-Aryl-1,3,3- and exo-2-Aryl-1,5,5-trimethylbicyclo[2,2,1] heptan-endo-2-ols
  作者：JM Coxon、PJ Steel

  DOI：10.1071/ch9792441

  日期：——

  The reactions of exo-2-aryl-1,3,3- and exo-2-aryl-1,5,5-trimethylbicyclo[2,2,1]heptan-endo-2-ols in strong acid are reported. The equilibration of 2-(4'-methoxyphenyl)-3,3,endo-6-trimethylbicyclo- [2,2,1]hept-2-yl cation and the exo-6-methyl isomer both formed from 2-(4'-methoxyphenyl)-1,3,3- trimethylbicyclo[2,2,1]hept-2-yl cation is considered to occur by an elimination-addition mechanism. At higher temperatures the bicyclic skeleton collapses to give monocyclic allylic cations. The 13C N.M.R. spectra of these ions are reported.

  报告了外-2-芳基-1,3,3-和外-2-芳基-1,5,5-三甲基双环[2,2,1]庚-内-2-醇在强酸中的反应。 2-(4'-甲氧基苯基)-3,3,内-6-三甲基双环[2,2,1]庚-2-醇阳离子和外-6-甲基异构体在强酸中的平衡均由 2-(4'-methoxyphenyl)-1,3,3- trimethylbicyclo[2,2,1]hept-2-yl 阳离子被认为是通过消去-加成机制发生的。在较高温度下 在较高温度下，双环骨架塌缩，生成单环烯丙基阳离子。 单环烯丙基阳离子。报告了这些离子的 13C N.M.R. 报告了这些离子的 13C N.M.R. 光谱。
• Welniak, Polish Journal of Chemistry, 1998, vol. 72, # 6, p. 1021 - 1027
  作者：Welniak

  DOI：——

  日期：——
• Welniak, Polish Journal of Chemistry, 2002, vol. 76, # 10, p. 1405 - 1411
  作者：Welniak

  DOI：——

  日期：——
• Anhydrous cerium(III) chloride — Effect of the drying process on activity and efficiency
  作者：Vladimir Dimitrov、Kalina Kostova、Miroslav Genov

  DOI：10.1016/s0040-4039(96)01479-7

  日期：1996.9

  The activity and efficiency of anhydrous CeCl3 depend strongly on the drying procedure. Deactivation of CeCl3 occurs during the drying process as a result of hydrolysis by the hydrate water, when heating above 90 degrees C. The highly active CeCl3, prepared by an improved drying procedure, is demonstrated to activate rapidly (in catalytic and stoichiometric amounts) ketones at room temperature, providing excellent addition of organometallic reagents. Copyright (C) 1996 Elsevier Science Ltd