(1R,3R)-3-butylcyclohexan-1-ol | 87759-32-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R)-3-butylcyclohexan-1-ol
• CAS: 87759-32-8
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: VBPWOJIXSLIBFJ-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• 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：

  甲氧基-三氟甲基苯 、 (1R,3R)-3-butylcyclohexan-1-ol 在 sodium tetrahydroborate 、 1,4-dihydronicotinamide adenine dinucleotide 、 horse liver alcohol dehydrogenase 、 (±)-α-甲氧基-α-(三氟甲基)苯乙酸 作用下， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,3R)-3-butyl-cyclohexyl ester 、 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,3S)-3-butyl-cyclohexyl ester 、 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,3R)-3-butyl-cyclohexyl ester 、 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,3S)-3-butyl-cyclohexyl ester
  参考文献：
  名称：

  Use of shift reagent with MTPA derivatives in19F NMR spectrocopy: IV—Determination of enantiomeric composition for a variety of secondary cycloalkanols. A survey

  摘要：

  AbstractChiral secondary cycloalkanols (monocyclic alcohols) are derivatized to the corresponding (R)‐α‐methoxy‐α‐trifluoromethyl‐α‐phenylacetic acid [(R)‐MTPA] esters and analysed by 19F NMR in the presence of tris(6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedionato) europium(III) [Eu(fod)3]. Using this method the enantiomeric composition can be measured for several cyclopentanols, cyclohexanols and cycloheptanols, with a variety of substitution patterns. It is shown that a mixture of four stereoisomeric cycloalkanols, such as cis and trans disubstituted alcohols, can be analysed simultaneously.

  DOI：

  10.1002/omr.1270210609
• 作为产物：
  描述：

  rac-3-butylcyclohexanone 在 sodium tetrahydroborate 、 molecular sieve 、 Lipase PS (Amano) 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.5h， 生成 (1R,3R)-3-butylcyclohexan-1-ol
  参考文献：
  名称：

  Lipase-mediated diastereoselective and enantioselective acetylations of 3-substituted cyclohexanols

  摘要：

  Lipase-mediated acetylation of four diastereomeric and enatiomeric isomers of 3-substituted cyclohexanols 2 has led to an efficient resolution to provide a single stereoisomer, (1R,3S)-cyclohexyl acetate (1R,3S)-3 in a high enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10705-5

文献信息

• Lipase-mediated diastereoselective and enantioselective acetylations of 3-substituted cyclohexanols
  作者：Rikuhei Tanikaga、Akira Morita

  DOI：10.1016/s0040-4039(97)10705-5

  日期：1998.2

  Lipase-mediated acetylation of four diastereomeric and enatiomeric isomers of 3-substituted cyclohexanols 2 has led to an efficient resolution to provide a single stereoisomer, (1R,3S)-cyclohexyl acetate (1R,3S)-3 in a high enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Use of shift reagent with MTPA derivatives in19F NMR spectrocopy: IV—Determination of enantiomeric composition for a variety of secondary cycloalkanols. A survey
  作者：E. M. Merckx、J. A. Lepoivre、G. L. Lemière、F. C. Alderweireldt

  DOI：10.1002/omr.1270210609

  日期：1983.6

  AbstractChiral secondary cycloalkanols (monocyclic alcohols) are derivatized to the corresponding (R)‐α‐methoxy‐α‐trifluoromethyl‐α‐phenylacetic acid [(R)‐MTPA] esters and analysed by 19F NMR in the presence of tris(6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedionato) europium(III) [Eu(fod)3]. Using this method the enantiomeric composition can be measured for several cyclopentanols, cyclohexanols and cycloheptanols, with a variety of substitution patterns. It is shown that a mixture of four stereoisomeric cycloalkanols, such as cis and trans disubstituted alcohols, can be analysed simultaneously.