(1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile | 406909-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile
• 英文别名: (1R,2S)-2-hydroxy-1-methylcyclohexanecarbonitrile；Cyclohexanecarbonitrile, 2-hydroxy-1-methyl-, (1R,2S)-；(1R,2S)-2-hydroxy-1-methylcyclohexane-1-carbonitrile
• CAS: 406909-97-5
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: GEHDSKKKZZPSQP-JGVFFNPUSA-N

物化性质

• 沸点：
  264.6±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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)-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
• 作为产物：
  描述：

  1,5-二氰基戊烷 在 吡啶硼烷 、 Candida antarctica lipase B "Novozym 435" 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 (1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile
  参考文献：
  名称：

  α，α-二取代的环状羟基腈的合成及酶动力学拆分

  摘要：

  在本文中，我们描述了五元和六元α，α-二取代的环状β-羟基腈的非对映选择性合成及其通过酶促酯交换反应的拆分。通过这种方法，以对映纯形式和高收率获得了所有可能的立体异构体。

  DOI：

  10.1021/jo035808r

文献信息

• G‐type Halohydrin Dehalogenases Catalyze Ring Opening Reactions of Cyclic Epoxides with Diverse Anionic Nucleophiles**
  作者：Jennifer Solarczek、Felix Kaspar、Pia Bauer、Anett Schallmey

  DOI：10.1002/chem.202202343

  日期：2022.12.27

  G-type halohydrin dehalogenases convert 5- and 6-membered cyclic epoxides with a range of small anionic C-, N-, O- and S-nucleophiles.

  G 型卤代醇脱卤酶通过一系列小阴离子 C-、N-、O- 和 S- 亲核试剂转化 5 元和 6 元环氧化物。
• Preparation of Enantiopure Ketones and Alcohols Containing a Quaternary Stereocenter through Parallel Kinetic Resolution of β-Keto Nitriles
  作者：Juan R. Dehli、Vicente Gotor

  DOI：10.1021/jo011092t

  日期：2002.3.1

  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.
• Synthesis and Enzymatic Kinetic Resolution of α,α-Disubstituted Cyclic Hydroxy Nitriles
  作者：Laura M. Levy、Vicente Gotor

  DOI：10.1021/jo035808r

  日期：2004.4.1

  Herein, we describe the diastereoselective synthesis of five- and six-membered α,α-disubstituted cyclic β-hydroxy nitriles and their resolution via enzymatic transesterification. By this method, all possible stereoisomers were obtained in enantiopure form and high yield.

  在本文中，我们描述了五元和六元α，α-二取代的环状β-羟基腈的非对映选择性合成及其通过酶促酯交换反应的拆分。通过这种方法，以对映纯形式和高收率获得了所有可能的立体异构体。