ethyl (Z)-3-ethyl-3-nitroacrylate | 52194-42-0

• 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)-3-ethyl-3-nitroacrylate
• 英文别名: Z-β-Nitro-penten-(2)-saeure-aethylester；ethyl (Z)-3-nitropent-2-enoate
• CAS: 52194-42-0
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: KYOQRVRMIDRZOR-WAYWQWQTSA-N

物化性质

• 沸点：
  249.3±23.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

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)-3-ethyl-3-nitroacrylate 在 titanium(III) chloride 、 ammonium acetate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以55%的产率得到丙酰乙酸乙酯
  参考文献：
  名称：

  硝基烷和乙二醛酸乙酯是制备β-酮酸酯和α，β-不饱和酯的常用前体

  摘要：

  通过硝基烷烃和乙二醛酸乙酯的反应获得的β-硝基丙烯酸酯是两种标题化合物立即合成的关键组成部分。实际上，它们用三氯化钛处理可直接转化为β-酮酯，而它们与氢化硼钠的反应是通过用氢正式取代乙烯基硝基而一锅合成α，β-不饱和酯。

  DOI：

  10.1016/j.tetlet.2004.07.141
• 作为产物：
  描述：

  α-Hydroxy-β-nitro-n-valeriansaeure-aethylester 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以85%的产率得到ethyl (Z)-3-ethyl-3-nitroacrylate
  参考文献：
  名称：

  硝基烷和乙二醛酸乙酯是制备β-酮酸酯和α，β-不饱和酯的常用前体

  摘要：

  通过硝基烷烃和乙二醛酸乙酯的反应获得的β-硝基丙烯酸酯是两种标题化合物立即合成的关键组成部分。实际上，它们用三氯化钛处理可直接转化为β-酮酯，而它们与氢化硼钠的反应是通过用氢正式取代乙烯基硝基而一锅合成α，β-不饱和酯。

  DOI：

  10.1016/j.tetlet.2004.07.141

文献信息

• Conjugate Addition of Indoles to Nitroalkenes Promoted by Basic Alumina in Solventless Conditions
  作者：Roberto Ballini、Roberto Rabanedo Clemente、Alessandro Palmieri、Marino Petrini

  DOI：10.1002/adsc.200505339

  日期：2006.1

  alumina is found to promote the conjugate addition of indoles to nitroalkenes in solventless conditions at 60 °C. Nitroalkenes can be replaced by nitro alcohols that are converted into nitroolefins under the reaction conditions. Alternatively, a tandem nitroaldol-dehydration allows the utilization of nitroalkanes and aldehydes as remote precursors of reactive nitroalkenes in a ‘one–pot’ synthesis of 3-substituted

  发现碱性氧化铝可在60°C无溶剂条件下促进吲哚与硝基烯烃的共轭加成。硝基烯烃可以被在反应条件下转化为硝基烯烃的硝基醇代替。另外，串联的硝基羟醛脱水可以在三取代的吲哚的“一锅法”合成中利用硝基烷和醛作为反应性硝基烯的遥远前体。
• Visible‐Light‐Driven Photocatalyst‐Free Preparation of ( <i>Z)</i> β‐Nitroacrylate Isomers
  作者：Muhammad Ehtisham Ibraheem Khan、Lorenzo Di Terlizzi、Stefano Protti、Alessandro Palmieri

  DOI：10.1002/ejoc.202200635

  日期：2022.7.14

  A new easy and efficient protocol for synthesizing poorly available (Z) β-nitroacrylates through visible-light driven conversion of the corresponding (E) isomers is reported. The process can be profitably performed under both batch and flow conditions.

  报道了一种通过相应 ( E ) 异构体的可见光驱动转换来合成低效 ( Z ) β-硝基丙烯酸酯的简单有效的新方案。该过程可以在分批和流动条件下有利地进行。
• REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED COMPOUNDS
  申请人：Oregon State University

  公开号：US20230117370A1

  公开（公告）日：2023-04-20

  Disclosed herein are embodiments of a method for making substituted compounds with specific and selectable regiochemistry. Also disclosed are compounds made by the method. The method may comprise contacting a compound having a formula I with a compound according to formula II in the presence of a Lewis acid to form a phenol compound according to formula III and/or a benzofuranone compound according to formula IV

  本文公开了一种制造具有特定和可选择区域化学性质的取代化合物的方法的实施例。还公开了用该方法制得的化合物。该方法可包括将具有式 I 的化合物 与根据式 II 的化合物接触 在路易斯酸存在下，生成根据式 III 的苯酚化合物和/或根据式 IV 的苯并呋喃酮化合物
• 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.
• Stereoselective Synthesis of Functionalized Chiral 2-Nitrocyclohexanecarboxylic Esters<i>via</i>Catalytic Dienamine Addition to β-Substituted β-Nitroacrylates
  作者：Elisabetta Massolo、Maurizio Benaglia、Rita Annunziata、Alessandro Palmieri、Giuseppe Celentano、Alessandra Forni

  DOI：10.1002/adsc.201301074

  日期：2014.2.10

  AbstractA metal‐free stereoselective catalytic addition of in situ generated dienamine to β‐nitroacrylates has been developed. Starting from simple α,β‐unsaturated ketones, highly functionalized chiral β‐nitrocyclohexanecarboxylic esters were obtained in a single step, in good yields and up to 98% ee. By an unprecedented mechanistic pathway, starting from the synthetically readily available E‐nitroacrylate, the present methodology allowed us to obtain as major product the isomer bearing a cis relative disposition between the nitro and the ester groups, which is not accessible via a classical Diels–Alder reaction.magnified image