(1R,2S)-1-(furan-2-yl)-2-nitropropan-1-ol

• 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: (1R,2S)-1-(furan-2-yl)-2-nitropropan-1-ol
• 英文别名: 1-(furan-2-yl)-2-nitropropan-1-ol
• 化学式: C₇H₉NO₄
• 分子量: 171.153
• InChiKey: VAJZYHHMLZZNTL-CAHLUQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  糠醛 、 硝基乙烷 在 (CuOTf)*toluene 、 C₂₇H₄₈N₄O₄ 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.5h， 以96%的产率得到
  参考文献：
  名称：

  通过手性硝基烷烃和醛催化不对称催化Henry反应Ñ，Ñ ' -氧化钛/铜（I）配合物的

  摘要：

  已开发出一种易于获得的N，N'-二氧化物/ Cu（I）络合物，用于醛与硝基乙烷的催化不对称硝基醛醇（Henry）反应。下温和的反应条件下，一系列的取代的芳族，杂芳族和α，β -不饱和醛转化为相应的抗-β-硝基醇以良好至优异的产率（高达99％）的中度至良好博士（高达1670： 1 anti / syn）和高ee值（高达97％）。除硝基乙烷外，还使用硝基甲烷和1-硝基丙烷作为亲核试剂，并获得了良好的对映选择性。

  DOI：

  10.1021/jo5027832

文献信息

• Novel Schiff base ligands derived from Cinchona alkaloids for Cu(II)-catalyzed asymmetric Henry reaction
  作者：Yu Wei、Lin Yao、Bangle Zhang、Wei He、Shengyong Zhang

  DOI：10.1016/j.tet.2011.08.076

  日期：2011.11

  A new series of Schiff bases derived from Cinchona alkaloids were developed as chiral ligands for the copper(II)-catalyzed asymmetric Henry reaction. The optimized catalyst can promote the Henry reaction of both aromatic and aliphatic aldehydes with nitromethane or nitroethane. Those reactions can afford the chiral β-nitro alcohol adducts with high enantioselectivities.

  开发了一系列从金鸡纳生物碱衍生的席夫碱，作为铜（II）催化的不对称亨利反应的手性配体。优化的催化剂可以促进芳香族和脂肪族醛与硝基甲烷或硝基乙烷的亨利反应。这些反应可以提供具有高对映选择性的手性β-硝基醇加合物。
• Promotion of Henry reactions using Cu(OTf)2 and a sterically hindered Schiff base: access to enantioenriched β-hydroxynitroalkanes
  作者：Lin Yao、Yu Wei、Pingan Wang、Wei He、Shengyong Zhang

  DOI：10.1016/j.tet.2012.08.029

  日期：2012.11

  The steric and electronic properties of chiral Schiff base ligands derived from cinchona alkaloids were evaluated in asymmetric Henry reactions. Amongst these, the sterically hindered ligand 2 showed outstanding catalytic efficiency in the Cu(II) catalyzed asymmetric addition of nitroalkanes to a variety of aldehydes to afford the desired adducts in high yields (up to 97%) with excellent enantioselectivities

  在不对称的亨利反应中评估了从金鸡纳生物碱衍生的手性席夫碱配体的空间和电子性质。其中，位阻配体2在Cu（II）催化的硝基链烷烃向多种醛的不对称加成反应中表现出出色的催化效率，从而以高收率（高达97％）提供了所需的加合物，并具有出色的对映选择性（高达99％） ee）和中等至良好的非对映选择性（最高达84:16 dr）。
• Chiral Tetraaminophosphonium Salt-Mediated Asymmetric Direct Henry Reaction
  作者：Daisuke Uraguchi、Sawako Sakaki、Takashi Ooi

  DOI：10.1021/ja075152+

  日期：2007.10.1

  Chiral tetraaminophosphonium salts 1 possessing the phosphorus-centered [5.5]-spirocyclic core have been designed and synthesized in a single step from L-valine-derived diamine. The three-dimensional molecular structure was successfully verified by the single-crystal X-ray diffraction analysis, which also identified a secondary interaction between the phosphonium cation and chloride ion via double hydrogen-bonding. The potential of this novel onium salt as a chiral organic molecular catalyst has been demonstrated in an application to asymmetric direct Henry reaction.
• Brucine-Derived Amino Alcohol Catalyzed Asymmetric Henry Reaction: An Orthogonal Enantioselectivity Approach
  作者：Hun Young Kim、Kyungsoo Oh

  DOI：10.1021/ol902380z

  日期：2009.12.17

  A new approach to both enantioenriched Henry products is developed by use of different molecularities of metal-ligand complexes generated from Cu(I) and Zn(II) metals with readily available chiral amino alcohol 1.
• Dual-reagent organocatalysis with a phosphine and electron-deficient alkene: application to the Henry reaction
  作者：Xiu Wang、Fan Fang、Chen Zhao、Shi-Kai Tian

  DOI：10.1016/j.tetlet.2008.08.092

  日期：2008.11

  Trip henylphosphine in combination with methyl acrylate was found to be able to catalyze the Henry (nitroaldol) reaction of various aldehydes and alpha-keto esters to give the corresponding beta-nitroalkanols in good to excellent yields, and a catalytic cycle involving a zwitterionic phosphine-alkene adduct was proposed for this dual-reagent organocatalysis according to the deuterium-labeling experiments with CD3NO2. (C) 2008 Elsevier Ltd. All rights reserved.