ethyl (Z)-2-nitromethylene-butanoate | 923271-71-0

• 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: ethyl (Z)-2-nitromethylene-butanoate
• 英文别名: ethyl (2Z)-2-(nitromethylidene)butanoate
• CAS: 923271-71-0
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: XSTIIZYTEPFCAD-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-2-nitromethylene-butanoate 在 葡萄糖 、 old yellow enzyme-1 、 重水 、 还原型辅酶Ⅰ 作用下， 以 aq. phosphate buffer 、 异丙醇 为溶剂， 反应 24.0h， 生成
  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：

  2-丁酮酸乙酯 在 Amberlyst A-21 resin 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl (Z)-2-nitromethylene-butanoate
  参考文献：
  名称：

  Asymmetric Bioreductions of β-Nitro Acrylates as a Route to Chiral β²-Amino Acids

  摘要：

  Reductions of beta-nitroacrylates by Saccharomyces carlsbergensis old yellow enzyme is the key step in a concise route to optically active beta(2)-amino acids. The enzymatic reductions occur with 87 - 96% ee, with larger substrates providing greater stereoselectivities. This work extends enantioselective enzymatic alkene reductions to include acyclic systems with weakly coordinating substituents.

  DOI：

  10.1021/ol062612f

文献信息

• Synthesis of Quaternary-Carbon-Containing β^2,2-Amino Acids by the Rh^I-Catalyzed Enantioselective Arylation of α-Substituted β-Nitroacrylates
  作者：Jo-Hsuan Fang、Jia-Hong Jian、Hao-Ching Chang、Ting-Shen Kuo、Way-Zen Lee、Ping-Yu Wu、Hsyueh-Liang Wu

  DOI：10.1002/chem.201604120

  日期：2017.2.3

  An enantioselective RhI‐catalyzed conjugate addition reaction of α‐substituted β‐nitroacrylates with various arylboronic acids by using chiral RhI diene catalysts is described for the first time. The addition reaction proceeds under mild conditions in a range of common organic solvents and additives, and it affords the corresponding quaternary‐carbon‐containing α,α‐disubstituted β‐nitropropionate products

  首次描述了使用手性Rh I二烯催化剂对α-取代的β-硝基丙烯酸酯与各种芳基硼酸的对映选择性Rh I催化的共轭加成反应。加成反应在温和的条件下在一系列常见的有机溶剂和添加剂中进行，从而以高达63％的收率和99％ee的产率提供相应的含季碳的α，α-二取代的β-硝基丙酸酯产品。（E）-或（Z）-β-硝基丙烯酸酯的反应提供了相同的产物对映异构体，并且可以耐受一系列的酯和芳基。为了证明该方法的实用性，乙基（R苯基）-1,1-二甲基-1-苯基-3- nitropropionate，制备本文中，转化成非蛋白原β 2,2 -氨基磺酸，（- [R）-2-（氨基甲基）-2-苯基丙酸和β ，2-内酰胺，（R）-3-甲基-3-苯基氮杂环丁烷-2-one。此外，三肽，其包括（comprised）升-苯丙氨酸，升-丙氨酸，β和2,2 -氨基酸7，还合成。
• Rationalisation of the stereochemical outcome of ene-reductase-mediated bioreduction of α,β-difunctionalised alkenes
  作者：Elisabetta Brenna、Michele Crotti、Francesco G. Gatti、Alessia Manfredi、Daniela Monti、Fabio Parmeggiani、Andrea Pugliese、Davila Zampieri

  DOI：10.1016/j.molcatb.2013.12.020

  日期：2014.3

  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.
• Asymmetric Bioreductions of β-Nitro Acrylates as a Route to Chiral β²-Amino Acids
  作者：Magdalena A. Swiderska、Jon D. Stewart

  DOI：10.1021/ol062612f

  日期：2006.12.1

  Reductions of beta-nitroacrylates by Saccharomyces carlsbergensis old yellow enzyme is the key step in a concise route to optically active beta(2)-amino acids. The enzymatic reductions occur with 87 - 96% ee, with larger substrates providing greater stereoselectivities. This work extends enantioselective enzymatic alkene reductions to include acyclic systems with weakly coordinating substituents.