(R)-2-butyl-2-methylmalonamic acid | 152384-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-butyl-2-methylmalonamic acid
• 英文别名: 2-carbamoyl-2-methylhexanoic acid；(2R)-2-carbamoyl-2-methylhexanoic acid
• CAS: 152384-46-8
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: MMAQVVLWNPSAAF-MRVPVSSYSA-N

物化性质

• 熔点：
  84.2-85.2 °C
• 沸点：
  357.8±25.0 °C(predicted)
• 密度：
  1.109±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-butyl-2-methylmalonamic acid 在 phosphorus pentoxide 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 (R)-2-Cyano-2-methyl-hexanoic acid methyl ester
  参考文献：
  名称：

  Asymmetric hydrolysis of a disubstituted malononitrile by the aid of a microorganism

  摘要：

  Rhodococcus rhodochrous ATCC 21197 hydrolyzed prochiral butylmethylmalononitrile to afford the corresponding amide-carboxylic acid with high enantiomeric excess. The reaction proceeds via the hydration of the starting dinitrile by a nitrile hydratase and the subsequent enantioselective hydrolysis of the intermediate diamide by an amidase.

  DOI：

  10.1016/s0957-4166(00)80214-1
• 作为产物：
  描述：

  2-butyl-2-methylmalononitrile 在 Rhodococcus rhodochrous IFO 15564 cells 作用下， 反应 24.0h， 以92%的产率得到(R)-2-butyl-2-methylmalonamic acid
  参考文献：
  名称：

  Realization of the synthesis of α,α-disubstituted carbamylacetates and cyanoacetates by either enzymatic or chemical functional group transformation, depending upon the substrate specificity of Rhodococcus amidase

  摘要：

  Substrate specificity and enantioselectivity of nitrile hydratase and amidase from R. rhodochrous IFO 15564 has been studied by applying a series of alpha,alpha-disubstituted malononitriles and related substrates. The amidase preferentially hydrolyzed the pro-(R) carbamyl group (amide) of the prochiral diamides, an intermediate resulting from the action of nitrile hydratase in a nonenantiotopic group-selective manner. The introduction of a fluorine atom at the alpha-position caused an inhibitory effect on amidase. By a combination of this microbial transformation and the subsequent Hofmann rearrangement, an important precursor of (S)methyldopa with 98.4% ee has been prepared. For the enzymatically poor substrate, the action on HO3SONO-H2O on the carbamyl group was effective, leaving the cyano group intact. This conversion is demonstrated as the key step for the expeditious preparation of (+/-)-alpha-cyano-alpha-fluoro-alpha-phenylacetic acid (CFPA) from diethyl alpha-fluoro-alpha-phenylmalonate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.047

文献信息

• 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.