ethyl 2-acetoxy-4-(4-methoxyphenyl)-3-nitrobut-(3E)-enoate | 1268720-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-acetoxy-4-(4-methoxyphenyl)-3-nitrobut-(3E)-enoate
• 英文别名: ethyl (E)-2-acetyloxy-4-(4-methoxyphenyl)-3-nitrobut-3-enoate
• CAS: 1268720-03-1
• 化学式: C₁₅H₁₇NO₇
• 分子量: 323.302
• InChiKey: AHYOAGVWRORUAO-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetoxy-4-(4-methoxyphenyl)-3-nitrobut-(3E)-enoate 、 2-氨基苯甲酰胺 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到(E)-ethyl 2-(2-carbamoylphenylamino)-4-(4-methoxyphenyl)-3-nitrobut-3-enoate
  参考文献：
  名称：

  Base and catalyst-free synthesis of nitrobenzodiazepines via a cascade N-nitroallylation-intramolecular aza-Michael addition involving o-phenylenediamines and nitroallylic acetates

  摘要：

  DOI：

  10.1016/j.tet.2019.130761

文献信息

• Highly Efficient Organocatalytic Kinetic Resolution of Activated Nitroallylic Acetates with Aldehydes via Conjugate Addition−Elimination
  作者：Raju Jannapu Reddy、Kwunmin Chen

  DOI：10.1021/ol200133y

  日期：2011.3.18

  A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a−i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition−elimination. The densely functionalized products 3a−o were obtained with excellent enantioselectivities (up to >99% ee), and unreacted substrates 1a−i were recovered

  已经开发出新颖，有效和空前的有机催化动力学拆分。第一次，通过共轭加成-消除反应，在2（2.5 mol％）存在下，各种醛基乙酸烯丙基酯1a - i用醛进行了拆分。获得具有优异的对映选择性（高达> 99％ee）的致密官能化产物3a - o，并且以良好至优异的光学纯度（高达98％ee）回收未反应的底物1a - i。
• An Efficient Friedel-Crafts/Oxa-Michael/Aromatic Annulation: Rapid Access to Substituted Naphtho[2,1-<i>b</i>]furan, Naphtho[1,2-<i>b</i>]furan, and Benzofuran Derivatives
  作者：Shaik Anwar、Wan-Yun Huang、Chih-Hao Chen、You-Song Cheng、Kwunmin Chen

  DOI：10.1002/chem.201204221

  日期：2013.3.25

  naphthofurans and benzofurans are easily accessible by treatment of naphthols/substituted phenols with nitroallylic acetates through a substitution–elimination process promoted by cesium carbonate. Reactions between naphthols and aromatic/heteroaromatic‐substituted nitroallylic acetates gave the desired functionalized naphthofurans in high to excellent chemical yields (14–97 %). On the other hand, treatment of

  通过碳酸铯促进的取代-消除过程，用硝基烯丙基乙酸酯处理萘酚/取代的苯酚很容易获得取代的萘呋喃和苯并呋喃。萘酚与芳族/杂芳族取代的硝基烯丙基乙酸酯之间的反应以高至极好的化学收率（14-97％）提供了所需的官能化萘呋喃。另一方面，用各种硝基烯丙基乙酸酯处理苯酚衍生物（即3-二甲氨基，3-甲氧基和3,5-二甲氧基苯酚）可得到相应的苯并呋喃，其化学收率中等至良好（24-91％）。该反应通过有趣的Friedel-Crafts S N 2'过程进行，然后进行分子内的氧杂-Michael环化和随后的芳构化。对数图（k/ ķ ħ）针对哈米特常数σ p表明良好的线性具有正ρ值，表明初始的Friedel-Crafts型S Ñ 2'处理过程构成的速率决定步骤。该方法已被用于以邻苯二酚和间苯三酚为亲核伴侣的各种新颖的C 2和C 3对称的双呋喃和三呋喃的合成。当使用烷基取代的硝基烯丙基乙酸酯体系时，反应性降低。这可能与这些底物的亲电子特性降低有关。
• Three-Component Organocascade Kinetic Resolution of Racemic Nitroallylic Acetates via Sequential Iminium/Enamine Asymmetric Catalysis
  作者：Suparna Roy、Kwunmin Chen

  DOI：10.1021/ol300783e

  日期：2012.5.18

  Nitroallylic acetates 1a–f have been kinetically resolved via an asymmetric three-component coupling that involves indoles, acrolein, and nitroolefin allylic acetates and is mediated by the chiral catalyst 2 (5 mol %). The reactions proceed via iminium/enamine cascade catalysis. Both recovered starting substrates and reaction products are typically obtained in high chemical yield and in good to excellent

  硝基烯丙基乙酸酯1a – f已通过不对称的三组分偶联而动力学拆分，该偶联涉及吲哚，丙烯醛和硝基烯烃烯丙基乙酸酯，并由手性催化剂2（5 mol％）介导。反应通过亚胺/烯胺级联催化进行。回收的起始底物和反应产物通常都以高化学收率和良好至优异的对映体纯度获得（1a – f的ee为79–95％ee，3a – n的ee为83–99％ee ）。首次证明了高效的三组分有机级联动力学拆分。
• Correction to Three-Component Organocascade Kinetic Resolution of Racemic Nitroallylic Acetates via Sequential Iminium/Enamine Asymmetric Catalysis
  作者：Suparna Roy、Kwunmin Chen

  DOI：10.1021/ol503315p

  日期：2014.12.19

  Revised file containing experimental data and spectra. This material is available free of charge via the Internet at http://pubs.acs.org. This article is cited by 1 publications. Revised file containing experimental data and spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

  包含实验数据和光谱的修订文件。可通过Internet（http://pubs.acs.org）免费获得此材料。这篇文章被1个出版物引用。包含实验数据和光谱的修订文件。可通过Internet（http://pubs.acs.org）免费获得此材料。
• Synthesis of tetrahydrochromenes and dihydronaphthofurans <i>via</i> a cascade process of [3 + 3] and [3 + 2] annulation reactions: mechanistic insight for 6-<i>endo-trig</i> and 5-<i>exo-trig</i> cyclisation
  作者：Yeruva Pavankumar Reddy、V. Srinivasadesikan、Rengarajan Balamurugan、M. C. Lin、Shaik Anwar

  DOI：10.1039/d2ra08163f

  日期：——

  styrene derived Morita–Baylis–Hillman (MBH) acetates through a formal [3 + 3]/[3 + 2] annulation. The reaction proceeds through a cascade Michael/oxa-Michael pathway with moderate to good yields. A DFT study was carried out to account for the formation of the corresponding six and five-membered heterocycles via 6-endo-trig and 5-exo-trig cyclization.

  通过正式的 [3 + 3]/[3 + 2] 环化，用反式-β-硝基苯乙烯衍生的 Morita-Baylis-Hillman (MBH) 乙酸酯处理β-四氢萘酮，很容易获得取代的四氢苯并呋喃和二氢萘并呋喃。该反应通过级联 Michael/oxa-Michael 途径进行，收率适中。进行了 DFT 研究以解释通过6-内三角和 5-外三角环化形成相应的六元和五元杂环。