α-benzyl-α-methylmalonamide | 183676-97-3

• 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: α-benzyl-α-methylmalonamide
• 英文别名: 2-benzyl-2-methylmalonamide；benzyl-methyl-malonic acid diamide；Benzyl-methyl-malonsaeure-diamid；2-benzyl-2-methylpropanediamide
• CAS: 183676-97-3
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: OCNDMKOYPDSTKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-benzyl-α-methylmalonamide 在 sodium hydroxide 、 Rhodococcus sp. CGMCC 0497 、 phosphorus pentoxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (R)-(-)-2-cyano-2-methyl-3-phenylpropionic 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：

  2-benzyl-2-methylmalonic acid 在 ammonium hydroxide 、 硫酸 作用下， 生成 α-benzyl-α-methylmalonamide
  参考文献：
  名称：

  Meyer,H., Monatshefte fur Chemie, 1906, vol. 27, p. 1092

  摘要：

  DOI：

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。
• Microbial whole cell-catalyzed desymmetrization of prochiral malonamides: practical synthesis of enantioenriched functionalized carbamoylacetates and their application in the preparation of unusual α-amino acids
  作者：Li-Bin Zhang、De-Xian Wang、Mei-Xiang Wang

  DOI：10.1016/j.tet.2011.05.103

  日期：2011.8

  malonamides underwent enantioselective desymmetrization reaction to afford high yield of carbamoylacetic acids with moderate to excellent enantioselectivity. The synthetic application has been demonstrated with a multi-gram scale biocatalytic preparation of R-(−)-α-allyl-α-methyl-carbamoylacetic acid and its conversions to varied α,α-disubstituted α-amino acids of the interest of medicinal chemistry

  在非常温和的条件下，由含酰胺酶的微生物全细胞催化剂红球菌红球菌AJ270催化，对许多官能化的手性丙二酰胺进行对映选择性去对称化反应，以高产率得到氨基甲酰乙酸，且具有中等至优异的对映选择性。R -（-）-α-烯丙基-α-甲基氨基甲酰乙酸的多克级生物催化制备及其转化成药用目的各种α，α-二取代α-氨基酸的合成应用已得到证明化学。
• 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.
• Meyer,H., Monatshefte fur Chemie, 1906, vol. 27, p. 1092
  作者：Meyer,H.

  DOI：——

  日期：——
• Practical Synthesis of Optically Active α,α-Disubstituted Malonamic Acids through Asymmetric Hydrolysis of Malonamide Derivatives with <i>Rhodococcus</i> sp. CGMCC 0497
  作者：Zhong-Liu Wu、Zu-Yi Li

  DOI：10.1021/jo026691u

  日期：2003.3.1

  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.