2-(4-Nitrobuta-1,3-dienyl)furan | 20164-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(4-Nitrobuta-1,3-dienyl)furan
• CAS: 20164-02-7
• 化学式: C₈H₇NO₃
• 分子量: 165.148
• InChiKey: VVYPXKHTNVZRQI-UHFFFAOYSA-N

物化性质

• 沸点：
  286.8±23.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Nitrobuta-1,3-dienyl)furan 、 1,7-bis(4-methoxyphenyl)hepta-1,6-diene-3,5-dione 在 水 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到3-(furan-2-yl)-5-(4-methoxyphenyl)-2-((E)-3-(4-methoxyphenyl)acryloyl)-4-nitrocyclohexanone
  参考文献：
  名称：

  Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes

  摘要：

  The reaction of curcumins with nitroalkenes has been investigated for the first time. Highly functionalized cyclohexanones possessing three contiguous chiral centers with complete diastereoselectivity have been synthesized through an inter-intramolecular double Michael reaction involving curcumin and nitroalkene under extremely simple experimental conditions (K2CO3 in aqueous THF). Under identical conditions, curcumins react with alpha-bromonitroalkenes to afford dihydrofurans through an intermolecular Michael addition-intramolecular nucleophilic substitution (O-alkylation), which is analogous to an 'interrupted' Feist-Benary reaction. These novel transformations of curcumins empower us to expand the repertoire of curcumin based therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.017

文献信息

• N-Heterocyclic Carbene Catalyzed Homoenolate-Addition Reaction of Enals and Nitroalkenes: Asymmetric Synthesis of 5-Carbon-Synthon δ-Nitroesters
  作者：Biswajit Maji、Li Ji、Siming Wang、Seenuvasan Vedachalam、Rakesh Ganguly、Xue-Wei Liu

  DOI：10.1002/anie.201203449

  日期：2012.8.13

  Synthesizing synthons: The highly enantioselective title reaction is described. It employs catalytic amounts of N‐heterocyclic carbene precursors and transforms a broad range of nitroalkenes, such as nitrodienes, nitroenynes, and nitrostyrenes, through reaction with a broad range of enals, into δ‐nitroesters via homoenolate intermediates (see scheme).

  合成合成子：描述了高度对映选择性的标题反应。它利用催化量的N杂环卡宾前体，通过与多种烯类反应，通过均烯酸酯中间体将多种硝基链烯（如硝基二烯，硝基炔和硝基苯乙烯）转化为δ-硝基酯（参见方案）。
• Au-Catalyzed Formal Allylation of Diazo(thio)oxindoles: Application to Tandem Asymmetric Synthesis of Quaternary Stereocenters
  作者：Xiao-Yuan Cui、Yu-Lei Zhao、Yan-Mei Chen、Su-Zhen Dong、Feng Zhou、Hai-Hong Wu、Jian Zhou

  DOI：10.1021/acs.orglett.1c01399

  日期：2021.6.18

  using traditional alkylation methods under basic conditions. The approach enables a highly stereoselective synthesis of quaternary (thio)oxindoles via a formal allylation-asymmetric Michael addition sequence. These adducts are versatile synthons for spirocyclic (thio)oxindoles. Initial biological studies reveal that chiral thiooxindoles show promising antiproliferation activity that is better than that

  我们报告了使用烯丙基三甲基硅烷对重氮（硫代）吲哚进行有效的 Au（I）催化的形式烯丙基化，得到 3-烯丙基（硫代）吲哚，在碱性条件下使用传统的烷基化方法难以获得。该方法通过正式的烯丙基化-不对称迈克尔加成序列实现了季（硫代）羟吲哚的高度立体选择性合成。这些加合物是用于螺环（硫代）吲哚的多功能合成子。初步的生物学研究表明，手性硫代吲哚显示出比相应的羟吲哚更好的抗增殖活性。
• One-pot three component α-aminoalkylation of conjugated nitroalkenes and nitrodienes
  作者：Kunjanpillai Rajesh、Pramod Shanbhag、Manjoji Raghavendra、Pallavi Bhardwaj、Irishi N.N. Namboothiri

  DOI：10.1016/j.tetlet.2009.12.015

  日期：2010.2

  Nitroethylenes possessing aryl, heteroaryl, and alkyl substituents at the beta-position as well as delta-substituted nitrobutadienes undergo facile aminoalkylation at the alpha-position upon treatment with formaldehyde and a secondary amine in the presence of imidazole and trifluoroacetic acid to afford alpha-aminoalkylated nitroalkenes and nitrodienes in good to excellent yield and stereoselectivity. (c) 2009 Elsevier Ltd. All rights reserved.
• Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes
  作者：Narasimham Ayyagari、Deena Jose、Shaikh M. Mobin、Irishi N.N. Namboothiri

  DOI：10.1016/j.tetlet.2010.11.017

  日期：2011.1

  The reaction of curcumins with nitroalkenes has been investigated for the first time. Highly functionalized cyclohexanones possessing three contiguous chiral centers with complete diastereoselectivity have been synthesized through an inter-intramolecular double Michael reaction involving curcumin and nitroalkene under extremely simple experimental conditions (K2CO3 in aqueous THF). Under identical conditions, curcumins react with alpha-bromonitroalkenes to afford dihydrofurans through an intermolecular Michael addition-intramolecular nucleophilic substitution (O-alkylation), which is analogous to an 'interrupted' Feist-Benary reaction. These novel transformations of curcumins empower us to expand the repertoire of curcumin based therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.