(R)-1-methyl-2-oxocyclohexanecarbonitrile | 5670-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-methyl-2-oxocyclohexanecarbonitrile
• 英文别名: (1R)-1-methyl-2-oxocyclohexane-1-carbonitrile
• CAS: 5670-51-9
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: FYAAAQWWVCFZAR-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  (R)-1-methyl-2-oxocyclohexanecarbonitrile 在 Mortierella isabellina NRRL 1757 作用下， 以 乙醇 、 水 为溶剂， 生成 (1R,2R)-2-hydroxy-1-methylcyclohexanecarbonitrile 、 (1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile
  参考文献：
  名称：

  Preparation of Enantiopure Ketones and Alcohols Containing a Quaternary Stereocenter through Parallel Kinetic Resolution of β-Keto Nitriles

  摘要：

  Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kinetic-resolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.

  DOI：

  10.1021/jo011092t
• 作为产物：
  描述：

  (1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以100%的产率得到(R)-1-methyl-2-oxocyclohexanecarbonitrile
  参考文献：
  名称：

  Preparation of Enantiopure Ketones and Alcohols Containing a Quaternary Stereocenter through Parallel Kinetic Resolution of β-Keto Nitriles

  摘要：

  Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kinetic-resolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.

  DOI：

  10.1021/jo011092t

文献信息

• Enantioselective Synthesis of 2-Alkyl-2-cyanocycloalkanones with a Quaternary Stereogenic Center
  作者：Dieter Enders、Andrea Zamponi、Gerhard Raabe、Jan Runsink

  DOI：10.1055/s-1993-25929

  日期：——

  2-Alkyl-2-cyanocycloalkanones 4 bearing a quaternary stereogenic center are synthesized in good overall yields and high enantiomeric excesses (ee = 90-95%) employing the SAMP-/RAMP-hydrazone method. The absolute configuration is confirmed by NMR-spectroscopic investigations on SAMP-hydrazone 3a and an X-ray structure analysis of SAMP-hydrazone 3f.

  采用 SAMP-/RAMP- 酰腙法合成了带有四元立体中心的 2-烷基-2-氰基环烷酮 4，总产率高，对映体过量率高（ee = 90-95%）。对 SAMP- hydrazone 3a 的核磁共振光谱研究和对 SAMP-hydrazone 3f 的 X 射线结构分析证实了其绝对构型。
• Enders Dieter, Zamponi Andrea, Raabe Gerhard, Runsink Jan, Synthesis, (1993) N 7, S 725-728
  作者：Enders Dieter, Zamponi Andrea, Raabe Gerhard, Runsink Jan

  DOI：——

  日期：——