ethyl 3-(furan-2-yl)-2-nitroacrylate | 73604-89-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-(furan-2-yl)-2-nitroacrylate
• 英文别名: ethyl (Z)-2-nitro-3-(2-furyl)propenoate；ethyl (Z)-3-(furan-2-yl)-2-nitroacrylate；(Z)-ethyl 2-nitro-3-(furan-2-yl)acrylate；ethyl (Z)-3-(furan-2-yl)-2-nitroprop-2-enoate
• CAS: 73604-89-4
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: LVCPHMLSIWYXMA-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(furan-2-yl)-2-nitroacrylate 以 氘代二甲亚砜 为溶剂， 反应 168.0h， 以41%的产率得到ethyl 3-(furan-2-yl)-2-nitroacrylate
  参考文献：
  名称：

  1 H NMR光谱法研究β-芳基（杂芳基）-α-硝基丙烯酸乙酯的几何异构

  摘要：

  根据α-硝基丙烯酸酯的β位上取代基的性质，氘代溶剂和样品的暴露时间，研究了α-硝基肉桂酸乙酯的Z → E异构化及其呋喃基和噻吩基杂类似物的特征。1 H NMR光谱。

  DOI：

  10.1134/s1070363216010102
• 作为产物：
  描述：

  N-(2-furylmethylene)aniline 、 硝基乙酸乙酯 在 乙酸酐 作用下， 反应 8.0h， 以39.86%的产率得到
  参考文献：
  名称：

  3,4,5-三取代异恶唑啉N-氧化物的催化对映选择性合成和3,4,5-三取代异恶唑的区域选择性合成

  摘要：

  已开发出方便的3,4,5-三取代的异恶唑啉N-氧化物的催化不对称合成和3,4,5-三取代的异恶唑的区域选择性合成。

  DOI：

  10.1002/ejoc.201801693

文献信息

• Water-compatible Cascade Reaction: An Efficient Route to Substituted 2,3-Dihydrofurans
  作者：Ya-Ru Zhang、Fang Luo、Xu-Jiao Huang、Jian-Wu Xie

  DOI：10.1246/cl.2012.777

  日期：2012.8.5

  A highly efficient domino Michael addition–alkylation reaction of 1,3-dicarbonyl derivatives with 2-nitroacrylates was developed in water. The procedure tolerates a series of functional groups such as methoxy, bromo, chloro, and heteroaromatic groups, providing three types of 2,3-dihydrofuran derivatives in moderate to good yields.

  在水中开发了一种高效的多米诺迈克尔加成-烷基化反应，通过1,3-二酮衍生物与2-硝基丙烯酸酯反应。该方法对一系列功能团（如甲氧基、溴、氯和杂环芳香族基团）具有良好的耐受性，提供了三种类型的2,3-二氢呋喃衍生物，产率中等至良好。
• Domino reactions for the synthesis of various α-substituted nitro alkenes
  作者：Stefania Fioravanti、Lucio Pellacani、Maria Cecilia Vergari

  DOI：10.1039/c1ob06260c

  日期：——

  Efficient one-pot methods for the synthesis of variously functionalised conjugated nitro alkenes have been reported. Despite the utility in different fields of these compounds, only a few multi-step syntheses have been reported in the literature, giving the target compounds in low overall yields. α-Nitro acrylates or cinnamates, α-nitro α,β-unsaturated ketones and, most importantly, aromatic and heteroaromatic

  已经报道了用于合成各种官能化的共轭硝基烯烃的有效的一锅法。尽管这些化合物在不同领域有实用性，但文献中仅报道了几步合成，以较低的总收率得到了目标化合物。以高收率获得了α-硝基丙烯酸酯或肉桂酸酯，α-硝基α，β-不饱和酮，以及最重要的是芳香族和杂芳香族（E）-2-硝基烯丙醇，这些化合物具有众所周知的抗癌活性。通过多米诺骨牌缩合脱水过程获得高非对映异构体纯度。
• Selective Amination Reactions of α-Nitro Aryl and Heteroaryl Enoates
  作者：Stefania Fioravanti、Lucio Pellacani、Maria Cecilia Vergari

  DOI：10.1021/jo4012859

  日期：2013.8.16

  Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various alpha-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-beta-amino alpha-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for alpha-nitro alkyl enoates or beta-nitro allylic alcohols.
• Synthesis of pyrrole- and indole-containing nitropropanoates on the basis of β-heteryl-α-nitroacrylates
  作者：L. V. Baichurina、R. I. Baichurin、N. I. Aboskalova、V. M. Berestovitskaya

  DOI：10.1134/s1070363210100221

  日期：2010.10

  Synthetic approach to beta-furyl- and beta-thienyl-alpha-nitroacrylates was modified. It was established that these nitroethenes react with pyrrole, N-methylpyrrole, and substituted indole derivatives in the absence of catalyst to afford products of the alkylation of pyrrole C-2 and indole C-3 reaction sites. A possibility of this reaction to proceed under "dry reaction" condition on a silicagel surface was shown.
• Catalytic Enantioselective Synthesis of 3,4,5-Trisubstituted Isoxazoline <i>N</i> -Oxides and Regioselective Synthesis of 3,4,5-Trisubstituted Isoxazoles
  作者：Subas Chandra Sahoo、Subhas Chandra Pan

  DOI：10.1002/ejoc.201801693

  日期：2019.2.14

  A convenient catalytic asymmetric synthesis of 3,4,5‐trisubstituted isoxazoline N‐oxides and regioselective synthesis of 3,4,5‐trisubstituted isoxazoles has been developed.

  已开发出方便的3,4,5-三取代的异恶唑啉N-氧化物的催化不对称合成和3,4,5-三取代的异恶唑的区域选择性合成。