(1R,2S,5R)-1-hydroxy-2-iso-propyl-5-methylcyclohex-1-yl-carbonitrile | 367939-58-0

• 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
• 英文名称: (1R,2S,5R)-1-hydroxy-2-iso-propyl-5-methylcyclohex-1-yl-carbonitrile
• 英文别名: (1R,2S,5R)-1-hydroxy-2-isopropyl-5-methylcyclohexanecarbonitrile；(1R,2S,5R)-1-hydroxy-5-methyl-2-(propan-2-yl)cyclohexane-1-carbonitrile；(1R,2S,5R)-1-hydroxy-5-methyl-2-propan-2-ylcyclohexane-1-carbonitrile
• CAS: 367939-58-0
• 化学式: C₁₁H₁₉NO
• 分子量: 181.278
• InChiKey: ZYUJMAOJFWVJHG-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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-iso-propyl-5-methylcyclohex-1-yl-carbonitrile 在 二异丁基氢化铝 、 硫酸 、 水 、 氯化铵 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 (1R,2S,5R)-1-hydroxy-5-methyl-2-propan-2-ylcyclohexane-1-carbaldehyde
  参考文献：
  名称：

  3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

  摘要：

  Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diasteroisomers (-)-38 and (-)-42. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.022
• 作为产物：
  描述：

  三甲基氰硅烷 、 (-)-薄荷酮 生成 (1R,2S,5R)-1-hydroxy-2-iso-propyl-5-methylcyclohex-1-yl-carbonitrile
  参考文献：
  名称：

  3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

  摘要：

  Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diasteroisomers (-)-38 and (-)-42. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.022

文献信息

• 13C NMR as a general tool for the assignment of absolute configuration
  作者：Iria Louzao、José Manuel Seco、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1039/c0cc02774j

  日期：——

  (13)C NMR, alone or in combination with (1)H NMR, allows the assignment of the absolute configuration of chiral alcohols, amines, carboxylic acids, thiols, cyanohydrins, sec,sec-diols and sec,sec-aminoalcohols, derivatized with appropriate chiral auxiliaries. This extends the assignment possibilities of NMR to fully deuterated and to nonproton containing compounds.

  （13）C NMR单独或与（1）H NMR结合使用，可以确定衍生化的手性醇，胺，羧酸，硫醇，氰醇，仲，仲二醇和仲，仲氨基醇的绝对构型与适当的手性助剂。这将NMR的赋值可能性扩展到了完全氘代和不含质子的化合物。
• The Use of a Single Derivative in the Configurational Assignment of Ketone Cyanohydrins
  作者：Iria Louzao、José M. Seco、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1002/ejoc.201001107

  日期：2010.12

  The absolute stereochemistry of ketone cyanohydrins can be easily determined by preparing a single MPA derivative. The comparison of two NMR spectra at different temperatures allows the assignment by just paying attention to the evolution of the cyanohydrin chemical shifts. The special case of α-aryl-substituted cyanohydrins is also described.

  通过制备单一的 MPA 衍生物，可以很容易地确定酮氰醇的绝对立体化学。不同温度下两个 NMR 光谱的比较允许通过只注意氰醇化学位移的演变来进行分配。还描述了 α-芳基取代的氰醇的特殊情况。
• Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde
  作者：Stefan Panev、Anthony Linden、Vladimir Dimitrov

  DOI：10.1016/s0957-4166(01)00206-3

  日期：2001.6

  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.