(1R,2S,5R)-1-hydroxy-2-isopropyl-5-methylcyclohex-1-yl-acetonitrile | 285560-35-2

• 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,2S,5R)-1-hydroxy-2-isopropyl-5-methylcyclohex-1-yl-acetonitrile
• 英文别名: 2-[(1S,2S,5R)-1-hydroxy-5-methyl-2-propan-2-ylcyclohexyl]acetonitrile
• CAS: 285560-35-2
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: YHATYPYCYDEAAB-GRYCIOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-1-hydroxy-2-isopropyl-5-methylcyclohex-1-yl-acetonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以84%的产率得到(1S,2S,5R)-1-(2'-aminoethyl)-2-iso-propyl-5-methylcyclohexan-1-ol
  参考文献：
  名称：

  Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  Novel chiral aminoalcohols were synthesized by highly diastereoselective addition of Me3SiCN and LICH2CN to (-)-menthone followed by LiAlH4 reduction. The addition of CH2=CH-MgBr and PhCH=CH-MgBr to menthone and the following epoxidation, provided useful hydroxy epoxides, one of which could be aminolyzed to afford an aminodiol. In one case, the configuration of the newly formed epoxidic stereogenic center was determined by X-ray crystallography. When applied as catalysts in the enantioselective addition of Et2Zn to benzaldehyde, the aminoalcohols induced enantiomeric excesses (e.e.s) of up to 77%. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00206-3
• 作为产物：
  描述：

  长叶薄荷酮 在 platinum(IV) oxide 氢气 、 lithium hexamethyldisilazane 作用下， 以 溶剂黄146 为溶剂， 20.0~25.0 ℃ 、303.98 kPa 条件下， 生成 (1R,2S,5R)-1-hydroxy-2-isopropyl-5-methylcyclohex-1-yl-acetonitrile
  参考文献：
  名称：

  An example of axial selectivity in nucleophilic additions to cyclohexanones and cyclohexenones

  摘要：

  DOI：

  10.1021/ja00236a067

文献信息

• First example of axial selectivity in the nucleophilic addition to (−)-menthone—addition of cyanomethyl lithium †Dedicated to Professor Dr. Manfred Hesse on the occasion of his 65th birthday. †
  作者：Vladimir Dimitrov、Stefan Panev

  DOI：10.1016/s0957-4166(00)00099-9

  日期：2000.4

  The addition of cyanomethyl lithium to (−)-menthone at −78°C followed by 1.5 h stirring at room temperature and acidic workup produced exclusively the axial addition product, being the first example of preferred axial attack of an organometallic reagent to menthone. In the case of hydrolysis at −78°C after 0.5 h reaction time the equatorial addition product was isolated as the preferably formed isomer

  在-78°C下将氰基甲基锂添加到（-）-薄荷酮中，然后在室温下搅拌1.5小时，然后进行酸性处理，仅产生了轴向加成产物，这是有机金属试剂对薄荷酮的优选轴向侵蚀的第一个例子。在0.5小时反应时间后在-78℃水解的情况下，分离出赤道加成产物作为优选形成的异构体。分别以高收率分离了轴向和赤道氰基甲基取代的薄荷醇和新薄荷醇。