3-Cyclopropyl-3-hydroxy-propionitrile | 1070966-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Cyclopropyl-3-hydroxy-propionitrile
• 英文别名: 3-Cyclopropyl-3-hydroxypropanenitrile
• CAS: 1070966-41-4
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: NVNVUGNBYVUNHW-UHFFFAOYSA-N

物化性质

• 沸点：
  273.0±13.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  3-Cyclopropyl-3-hydroxy-propionitrile 在 palladium on activated charcoal potassium phosphate buffer 、 Rhodococcus erythropolis AJ₂₇₀ whole cells 、 氢气 、 silver(l) oxide 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 (S)-3-Cyclopropyl-3-hydroxy-propionamide
  参考文献：
  名称：

  Dramatic Enhancement of Enantioselectivity of Biotransformations of β-Hydroxy Nitriles Using a Simple O-Benzyl Protection/Docking Group

  摘要：

  Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst, the O-benzylated beta-hydroxy alkanenitriles underwent remarkably high enantioselective biotransformations, whereas the biotransformations of free beta-hydroxy alkanenitriles gave very low enantioselectivity. The easy manipulations of O-protection and O-deprotection, excellent chemical and enantiomeric yields of biotransformations, along with the scalability render this enzymatic transformation attractive and practical for the synthesis of highly enantiopure beta-hydroxy alkanoic acids and their amide derivatives.

  DOI：

  10.1021/ol0610688

文献信息

• Nitrile Biotransformations for the Synthesis of Highly Enantioenriched β-Hydroxy and β-Amino Acid and Amide Derivatives: A General and Simple but Powerful and Efficient Benzyl Protection Strategy To Increase Enantioselectivity of the Amidase
  作者：Da-You Ma、De-Xian Wang、Jie Pan、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo800074k

  日期：2008.6.1

  Biotransformations of a number of racemic beta-hydroxy and beta-amino nitrile derivatives were studied using Rhodococcus erythropolis AJ270, the nitrile hydratase and amidase-containing microbial whole cell catalyst, under very mild conditions. The overall enantioselectivity of nitrile biotransformations was governed predominantly by the amidase whose enantioselectivity was switched on remarkably by an O- and a N-benzyl protection group of the Substrates. While biotransformations of beta-hydroxy and beta-amino alkanenitriles gave low yields of amide and acid products of very low enantiomeric purity, introduction of a simple benzyl protection group on the beta-hydroxy and beta-amino of nitrile substrates led to the formation of highly enantioenriched beta-benzyloxy and beta-benzylamino amides and acids in almost quantitative yield. The easy protection and deprotection operations, high chemical yield, and excellent enantioselectivity render the nitrile biotransformation a useful protocol in the synthesis of enantiopure beta-hydroxy and beta-amino acids.