(2S)-2-cyano-2-methyl-3-phenylpropanamide | 28052-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-cyano-2-methyl-3-phenylpropanamide
• 英文别名: (S)-2-cyano-2-methyl-3-phenylpropanamide
• CAS: 28052-45-1
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: KYMSWABNHRDGDX-NSHDSACASA-N

物化性质

• 沸点：
  407.3±38.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-cyano-2-methyl-3-phenylpropanamide 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 mercury(II) diacetate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (2R)-2-[(ethoxycarbonyl)amino]-2-methyl-3-phenylpropanoic acid ethyl ester
  参考文献：
  名称：

  Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497

  摘要：

  A new application of nitrile-converting enzymes in the synthesis of optically active alpha,alpha-disubstituted-alpha-cyanoacetamides from alpha,alpha-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral alpha,alpha-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00456-7
• 作为产物：
  描述：

  2-苄基丙二腈 在 Rodococcus sp. CGMCC 0497 、 potassium carbonate 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 反应 66.0h， 生成 (2S)-2-cyano-2-methyl-3-phenylpropanamide
  参考文献：
  名称：

  Practical Synthesis of Optically Active α,α-Disubstituted Malonamic Acids through Asymmetric Hydrolysis of Malonamide Derivatives with Rhodococcus sp. CGMCC 0497

  摘要：

  A variety of alpha,alpha-disubstituted malonamides undergo enantioselective hydrolysis with Rhodococcus sp. CGMCC 0497 to give challenging enantiopure alpha,alpha-disubstituted malonamic acids with up to >99% enantiomeric excesses and 98% chemical yields. The enantioselectivity originated from the effects of a highly enantioselective amidase. The products could be converted to valuable (R)or (S)-alpha,alpha-dialkylated amino acids after routine conversions.

  DOI：

  10.1021/jo026691u

文献信息

• Highly enantioselective synthesis of α,α-disubstituted malonamic acids through asymmetric hydrolysis of dinitriles with Rhodococcus sp. CGMCC 0497Electronic supplementary information (ESI) available: full experimental details. See http://www.rsc.org/suppdata/cc/b2/b210743k/
  作者：Zhong-Liu Wu、Zu-Yi Li

  DOI：10.1039/b210743k

  日期：2003.1.23

  Highly enantioselective hydrolysis of α,α-disubstituted malononitriles by the strain Rhodococcus sp. CGMCC 0497 expressing both nitrile hydratase and amidase activity to give (R)-α,α-disubstituted malonamic acids which could be converted to valuable (R)- or (S)-α-alkylated amino acids are reported and the yields of the products are improved remarkably at a lower reaction temperature.

  报告了表达腈水解酶和酰胺酶活性的 Rhodococcus sp. CGMCC 0497 菌株对δ,δ-二取代丙二腈的高对映选择性水解，得到(R)-δ,δ-二取代丙二酸，这些丙二酸可转化为有价值的(R)-或(S)-δ-烷基化氨基酸。
• Asymmetric nitrile-hydration with bifunctional ruthenium catalysts bearing chiral N-sulfonyldiamine ligands
  作者：Shoko Kamezaki、Satoshi Akiyama、Yoshihito Kayaki、Shigeki Kuwata、Takao Ikariya

  DOI：10.1016/j.tetasy.2010.03.011

  日期：2010.5

  The asymmetric hydration of alpha-benzyl-alpha-methylmalononitrile was examined by using chiral bifunctional catalysts. Enantiomer discrimination of the prochiral dinitrile in the presence of water was demonstrated with a well-defined bifunctional amido-Ru complex having N-sulfonyldiamine ligands, and providing the corresponding amidato(amine) complexes diastereoselectively. Under the catalytic conditions, the (R)-cyanoamide was successfully obtained without further hydrolysis to carboxylic acids. (C) 2010 Elsevier Ltd. All rights reserved.