ethyl 3-nitro-5-phenylpent-2-enoate | 1038619-06-5

• 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 3-nitro-5-phenylpent-2-enoate
• CAS: 1038619-06-5
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: MJAQKLNWUMEEGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-nitro-5-phenylpent-2-enoate 在 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene 作用下， 以 乙腈 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  β-Nitroacrylates as Useful Building Blocks for the Synthesis of Alkyl Indole-2-Carboxylates

  摘要：

  Polyfunctionalized alkyl indole 2-carboxylates can be easily synthesized starting form -nitroacrylates and o-bromoanilines through an addition-elimination process followed by an intramolecular palladium-catalyzed Heck reaction.

  DOI：

  10.1055/s-0033-1340075

文献信息

• Michael Reaction of Nitroalkanes with β-Nitroacrylates under a Solid Promoter: Advanced Regio- and Diastereoselective Synthesis of Nitro-Functionalized α,β-Unsaturated Esters and 1,3-Butadiene-2-carboxylates
  作者：Alessandro Palmieri、Serena Gabrielli、Roberto Ballini

  DOI：10.1002/adsc.201000142

  日期：——

  of nitro‐functionalized α,β‐unsaturated esters has been prepared by a regio‐ and diastereoselective Michael addition of nitroalkanes to β‐nitroacrylates, performed at room temperature, under carbonate on polymer as promoter, and in the presence of ethyl acetate as eco‐friendly solvent. Moreover, by the modular choice of the reaction conditions the method allows the synthesis of 1,3‐butadiene‐2‐carboxylates

  在室温下，在碳酸酯作为助催化剂的聚合物上，在室温下，通过将硝基烷烃进行区域和非对映选择性迈克尔加成到β-硝基丙烯酸酯中，制备了一类新型的硝基官能化的α，β-不饱和酯。作为环保溶剂。此外，通过模块化选择反应条件，该方法可以合成1,3-丁二烯-2-羧酸盐。
• Boosting Conjugate Addition to Nitroolefins Using Lithium Tetraorganozincates: Synthetic Strategies and Structural Insights
  作者：Marzia Dell'Aera、Filippo Maria Perna、Paola Vitale、Angela Altomare、Alessandro Palmieri、Lewis C. H. Maddock、Leonie J. Bole、Alan R. Kennedy、Eva Hevia、Vito Capriati

  DOI：10.1002/chem.202001294

  日期：2020.7.17

  We report the first transition metal catalyst‐ and ligand‐free conjugate addition of lithium tetraorganozincates (R4ZnLi2) to nitroolefins. Displaying enhanced nucleophilicity combined with unique chemoselectivity and functional group tolerance, homoleptic aliphatic and aromatic R4ZnLi2 provide access to valuable nitroalkanes in up to 98 % yield under mild conditions (0 °C) and short reaction time

  我们报道了四有机锌酸锂（R 4 ZnLi 2）向硝基烯烃的首次过渡金属催化剂和无配体共轭加成。显示出增强的亲核性，结合独特的化学选择性和官能团耐受性，均相脂肪族和芳香族R 4 ZnLi 2在温和的条件下（0°C）和短的反应时间（30分钟）可以高达98％的产率获得有价值的硝基烷。当使用β-硝基丙烯酸酯和β-硝基烯酮时，这尤其显着，尽管存在其他亲电子基团，但在C = C上选择性地加成1,4是优选的。结构和光谱学研究证实了溶液中四有机锌酸盐物种的形成，其性质一直是一个长期争论不休的问题，并允许揭示供体添加剂在这些试剂的聚集和结构中所起的关键作用。因此，在螯合N，N，N'，N'-四甲基乙二胺（TMEDA）和（R，R）-N，N，N'，N'-四甲基-1,2-二氨基环己烷（TMCDA）有助于形成接触离子对的锌酸盐，大环路易斯供体12-crown-4触发Et 4 ZnLi 2立即分解为等摩尔量的溶剂分离的Et
• β-Nitroacrylates as Precursors of Tetrasubstituted Furans in a One-Pot Process and under Acidic Solvent-Free Conditions
  作者：Alessandro Palmieri、Roberto Ballini、Serena Gabrielli

  DOI：10.1055/s-0030-1258031

  日期：2010.10

  The reaction of α-functionalized carbonyl derivatives with β-nitroacrylates, catalyzed by acidic alumina and in the absence of solvent, allows the one-pot synthesis of tetrasubstituted furan derivatives, in which at least two powerful functionalities are present in the 3- and 4-positions.

  在酸性氧化铝的催化下，δ官能化的羰基衍生物与δ-硝基丙烯酸酯在无溶剂的条件下发生反应，从而实现了四取代呋喃衍生物的一次合成，其中在 3 位和 4 位至少存在两个强力官能团。
• Solvent-Free, <i>anti</i>-Michael Addition of Active Methylene Derivatives to β-Nitroacrylates: Eco-Friendly, Chemoselective Synthesis of Polyfunctionalized Nitroalkanes
  作者：Roberto Ballini、Giovanna Bosica、Alessandro Palmieri、Khadijeh Bakhtiari

  DOI：10.1055/s-0028-1087515

  日期：——

  The chemoselective, anti-Michael addition of active ­methylene derivatives to β-nitroacrylates can be easily performed at room temperature, under solvent-free conditions, using a catalytic amount of potassium carbonate as heterogeneous catalyst.

  使用催化量的碳酸钾作为异相催化剂，可在室温、无溶剂条件下轻松实现活性亚甲基衍生物与δ-硝基丙烯酸酯的化学选择性反迈克尔加成。
• Fast, mild, eco-friendly synthesis of polyfunctionalized pyrroles from β-nitroacrylates and β-enaminones
  作者：Alessandro Palmieri、Serena Gabrielli、Cristina Cimarelli、Roberto Ballini

  DOI：10.1039/c1gc16012e

  日期：——

  The reaction of β-nitroacrylates with β-enaminones, at room temperature and under solvent- and promoter-free conditions, affords the one-pot synthesis of polyfunctionalized pyrroles in high yields.

  β-硝基丙烯酸酯与β-烯酮的反应，在室温和室温下进行 溶剂-且无助催化剂的条件，可一锅合成多官能团 吡咯 高产。