2-(4-methylbenzyl)-2-methylmalononitrile | 533928-80-2

• 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: 2-(4-methylbenzyl)-2-methylmalononitrile
• 英文别名: 2-Methyl-2-[(4-methylphenyl)methyl]propanedinitrile；2-methyl-2-[(4-methylphenyl)methyl]propanedinitrile
• CAS: 533928-80-2
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: KMDOMDMTAWTISH-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±27.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-methylbenzyl)-2-methylmalononitrile 在 Rhodococcus sp. CGMCC 0497 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 反应 168.0h， 以58%的产率得到(R)-2-(4'-methylbenzyl)-2-methylmalonamic acid
  参考文献：
  名称：

  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/

  摘要：

  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。

  DOI：

  10.1039/b210743k
• 作为产物：
  描述：

  (4-甲基苄基)丙二腈 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-(4-methylbenzyl)-2-methylmalononitrile
  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

文献信息

• Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497
  作者：Zhong-Liu Wu、Zu-Yi Li

  DOI：10.1016/s0957-4166(03)00456-7

  日期：2003.8

  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.
• 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。