2-methyl-2-propylmalononitrile | 794586-36-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-methyl-2-propylmalononitrile
• 英文别名: 2-Methyl-2-propylmalononitrile；2-methyl-2-propylpropanedinitrile
• CAS: 794586-36-0
• 化学式: C₇H₁₀N₂
• 分子量: 122.17
• InChiKey: FXDKLYBFEHSIKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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-methyl-2-propylmalononitrile 在 双氧水 作用下， 生成 2-methyl-2-propylmalonamide
  参考文献：
  名称：

  微生物全细胞催化手性丙二酰胺的脱对称：富含对映体的官能化氨基甲酰乙酸酯的实际合成及其在制备异常α-氨基酸中的应用

  摘要：

  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。

  DOI：

  10.1016/j.tet.2011.05.103

文献信息

• 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
  作者：Masahiro Yokoyama、Mieko Kashiwagi、Masakazu Iwasaki、Ken-ichi Fuhshuku、Hiromichi Ohta、Takeshi Sugai

  DOI：10.1016/j.tetasy.2004.04.047

  日期：2004.9

  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.