(R)-3-(furan-2-yl)-2,2-dimethyl-4-nitrobutanal

• 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: (R)-3-(furan-2-yl)-2,2-dimethyl-4-nitrobutanal
• 英文别名: (r)-3-(2-Furyl)-2,2-dimethyl-4-nitrobutanal；(3R)-3-(furan-2-yl)-2,2-dimethyl-4-nitrobutanal
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: JQJXIRODANROQK-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 异丁醛 在 (S)-1-(pyrrolidine-2-ylmethyl)-1H-pyrazole 、 苯甲酸 作用下， 以 neat (no solvent) 为溶剂， 反应 36.33h， 以85%的产率得到(R)-3-(furan-2-yl)-2,2-dimethyl-4-nitrobutanal
  参考文献：
  名称：

  吡咯烷-吡唑催化的α，α-二取代醛对硝基烯烃的对映选择性迈克尔加成

  摘要：

  为α的不对称催化Michael加成的高效的协议，α二取代的醛与吡咯烷吡唑nitroolefins进行说明。期望的产物γ-nitrocarbonyl化合物具有全碳季中心，是在良好的产率和高对映选择性的水平的无溶剂反应条件下获得的，使用苯甲酸作为添加剂。

  DOI：

  10.1016/j.tetasy.2014.06.009

文献信息

• Highly enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins
  作者：Xing-Tao Guo、Feng Sha、Xin-Yan Wu

  DOI：10.1007/s11164-016-2468-0

  日期：2016.7

  A highly enantioselective Michael addition reaction of α,α-disubstituted aldehydes to β-nitrostyrenes has been developed. In the presence of rosin-based chiral primary amine-thiourea, γ-nitroaldehydes were afforded in excellent enantioselectivities (up to 99 % ee) with up to 99 % yield.

  已经开发出α，α-二取代醛对β-硝基苯乙烯的高度对映选择性迈克尔加成反应。在基于松香的手性伯胺-硫脲的情况下，以极高的对映选择性（高达99％ee）提供了γ-硝基醛，产率高达99％。
• Synthesis of γ-nitroaldehydes containing quaternary carbon in the α-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst
  作者：Jelena Radivojevic、Gordana Minovska、Lidija Senerovic、Kevin O'Connor、Predrag Jovanovic、Vladimir Savic、Zorana Tokic-Vujosevic、Jasmina Nikodinovic-Runic、Veselin Maslak

  DOI：10.1039/c4ra05517a

  日期：——

  Synthetically valuable quaternary carbon containing γ-nitroaldehydes were obtained from branched chain aldehydes and a range of α,β-unsaturated nitroalkenes by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst.

  从支链醛和一系列α，β-不饱和硝基烯烃中，通过使用4-草酮丙烯酸异构酶作为催化剂的全细胞生物催化反应，合成了含有γ-硝基醛的对太碳。
• Readily Accessible 9-epi-amino Cinchona Alkaloid Derivatives Promote Efficient, Highly Enantioselective Additions of Aldehydes and Ketones to Nitroolefins
  作者：Séamus H. McCooey、Stephen J. Connon

  DOI：10.1021/ol0628006

  日期：2007.2.1

  from commercially available starting materials, have been shown to promote highly enantio- and diastereoselective Michael-type addition reactions between enolizable carbonyl compounds and nitroalkenes of broad scope. The influence of both the absolute and relative stereochemistry at C-9 on catalyst performance has also been assessed. [reaction: see text].

  通过一锅法可从市售原料中获得的简单金鸡纳生物碱衍生物已显示出可促进可烯丙基的羰基化合物与广泛范围的硝基烯烃之间的高度对映和非对映选择性迈克尔型加成反应。还评估了C-9处绝对和相对立体化学对催化剂性能的影响。[反应：请参见文字]。
• Highly enantioselective Michael addition of aldehydes to nitroolefins catalyzed by primary amine thiourea organocatalysts
  作者：Jia-Rong Chen、You-Quan Zou、Liang Fu、Fan Ren、Fen Tan、Wen-Jing Xiao

  DOI：10.1016/j.tet.2010.05.056

  日期：2010.7

  Asymmetric Michael addition reactions of aldehydes to nitroolefins have been successfully initiated by a series of primary amine thiourea bifunctional catalysts, with high enantioselectivities (90–98% ee) and excellent yields (80–96%). The privileged quinine scaffold was found to be essential to the reaction efficiency and enantioselectivity.

  一系列伯胺硫脲双功能催化剂具有高对映选择性（90-98％ee）和优异的收率（80-96％），已成功地引发了醛与硝基烯烃的迈克尔不对称迈克尔加成反应。发现特权的奎宁支架对于反应效率和对映选择性是必不可少的。
• Solvent-Free Enantioselective Michael Reactions Catalyzed by a Calixarene-Based Primary Amine Thiourea
  作者：Nicola Alessandro De Simone、Sara Meninno、Carmen Talotta、Carmine Gaeta、Placido Neri、Alessandra Lattanzi

  DOI：10.1021/acs.joc.8b01454

  日期：2018.9.7

  ability in enantioselective Michael additions. The reactions were found to conveniently proceed under solvent-free conditions, observing good to high enantioselectivities. From this preliminary study, the calix[4]arene unit is likely to play a role in affecting the conversion and to a lesser extent to the stereochemical outcome of the reactions through van der Waals contacts and C–H···π interactions with

  为了研究其在对映选择性迈克尔加成反应中的催化能力，合成了安装在（R，R）-1,2-环己二胺支架上的上边缘功能化杯[4]芳烃基硫脲。发现反应在无溶剂条件下方便地进行，观察到良好至高对映选择性。根据这项初步研究，杯芳烃[4]芳烃单元可能会通过范德华接触和C–H···π相互作用与范德华接触并在较小程度上影响反应的立体化学结果，从而影响转化率。基材。