(E)-propyl 3-cyano-5-methylhex-2-enoate | 1421868-97-4

• 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: (E)-propyl 3-cyano-5-methylhex-2-enoate
• 英文别名: propyl (E)-3-cyano-5-methylhex-2-enoate
• CAS: 1421868-97-4
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: MWBRXXHSVRJKPE-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-propyl 3-cyano-5-methylhex-2-enoate 在 glutamate dehydrogenase 、 葡萄糖 、 old yellow enzyme-1 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 24.0h， 以99%的产率得到
  参考文献：
  名称：

  Rationalisation of the stereochemical outcome of ene-reductase-mediated bioreduction of α,β-difunctionalised alkenes

  摘要：

  The OYE1-3-mediated reductions of some alpha,beta-difunctionalised alkenes, showing on the double bond a nitrile and ester group, are submitted to a careful stereochemical analysis, in order to identify which of the two electron-withdrawing groups (EWGs) is responsible for the activation of the C=C double bond towards reduction and for establishing hydrogen bond interactions within the binding pocket of the enzymes. The results show that for most of these substrates the activating EWG is the CN moiety linked to the prostereogenic olefinic carbon atom. The final stereochemical outcome can be explained through the empirical model which has been recently developed for difunctionalised alkenes activated by carbonyl/carboxyl containing EWGs.In a single case the activation is due to the COOR group linked to the less substituted olefinic carbon atom: an alternative empirical model is established for this kind of substrates, taking into consideration the OYE-catalysed reductions of beta,beta'-disubstituted-a-monofunctionalised alkenes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.12.020
• 作为产物：
  描述：

  4-甲基-2-戊酮 在 盐酸 、 四(三苯基膦)钯 、 四甲基氢氧化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 157.17h， 生成 (E)-propyl 3-cyano-5-methylhex-2-enoate
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Synthesis of Pregabalin Precursors via Asymmetric Bioreduction of β-Cyanoacrylate Esters Using Ene-Reductases

  摘要：

  The asymmetric bioreduction of a library of beta-cyanoacrylate esters using ene-reductases was studied with the aim to provide a biocatalytic route to precursors for GABA analogues, such as pregabalin. The stereochemical outcome could be controlled by substrate-engineering through size-variation of the ester moiety and by employing stereochemically pure (E)- or (Z)-isomers, which allowed to access both enantiomers of each product in up to quantitative conversion in enantiomerically pure form. In addition, stereoselectivities and conversions could be improved by mutant variants of OPR1, and the utility of the system was demonstrated by preparative-scale applications.

  DOI：

  10.1021/jo302484p