(R)-1-[1-(4-nitrophenyl)-2-nitroethyl]cyclopentanecarbaldehyde | 1609238-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-[1-(4-nitrophenyl)-2-nitroethyl]cyclopentanecarbaldehyde
• 英文别名: 1-[(1R)-2-nitro-1-(4-nitrophenyl)ethyl]cyclopentane-1-carbaldehyde
• CAS: 1609238-77-8
• 化学式: C₁₄H₁₆N₂O₅
• 分子量: 292.291
• InChiKey: VQYUJNACXFQZPC-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环戊基甲醛 、 1-硝基,2-(4-硝基苯基)-乙烯 在 (S)-2-(pyrrolidin-2-ylmethoxy)isoindoline-1,3-dione 、 对硝基苯甲酸 作用下， 以 neat (no solvent) 为溶剂， 反应 48.33h， 以93%的产率得到(R)-1-[1-(4-nitrophenyl)-2-nitroethyl]cyclopentanecarbaldehyde
  参考文献：
  名称：

  吡咯烷-氧酰亚胺催化的α，α-二取代醛向硝基烯烃的不对称迈克尔加成

  摘要：

  报道了使用吡咯烷-氧酰亚胺催化剂将α，α-二取代醛有机催化对映选择性迈克尔加成到硝基烯烃上。该反应在纯净条件下在0°C下以15 mol％的催化剂和10 mol％的对硝基苯甲酸为添加剂可有效地进行；这导致形成具有全碳四元中心并具有良好收率和对映选择性的迈克尔加合物。

  DOI：

  10.1016/j.tetasy.2015.07.009

文献信息

• Enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins catalyzed by a pyrrolidine-pyrazole
  作者：Togapur Pavan Kumar、Kothapalli Haribabu

  DOI：10.1016/j.tetasy.2014.06.009

  日期：2014.8

  efficient protocol for the asymmetric catalytic Michael additions of α,α-disubstituted aldehydes to nitroolefins with a pyrrolidine-pyrazole is described. The desired products γ-nitrocarbonyl compounds possessing an all-carbon quaternary center, were obtained in good yields and with high levels of enantioselectivities under solvent-free reaction conditions, employing benzoic acid as an additive.

  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。
• Highly efficient asymmetric organocatalytic Michael addition of α,α-disubstituted aldehydes to nitroolefins under solvent-free conditions
  作者：Junpeng He、Qiankun Chen、Bukuo Ni

  DOI：10.1016/j.tetlet.2014.03.107

  日期：2014.5

  with benzoic acid has been found to be an effective organocatalyst for Michael addition of α,α-disubstituted aldehydes with nitroolefins. The reaction provided the desired Michael products possessing all-carbon quaternary center with high yields (76–98%) and high levels of enantioselectivities (up to 97% ee) under solvent-free reaction conditions. The procedure presented is simple and makes this method

  已发现手性基于吡咯化物的二胺与苯甲酸组合是有效的有机催化剂，用于将α，α-二取代的醛与硝基烯烃迈克尔加成。该反应提供了所需的迈克尔产物，该产物具有全碳季铵盐中心，在无溶剂的反应条件下，具有高收率（76-98％）和高水平的对映选择性（高达97％ee）。所介绍的过程很简单，使该方法适合实际使用。
• Pyrrolidine–oxyimide catalyzed asymmetric Michael addition of α,α-disubstituted aldehydes to nitroolefins
  作者：Togapur Pavan Kumar

  DOI：10.1016/j.tetasy.2015.07.009

  日期：2015.9

  Organocatalytic enantioselective Michael addition of α,α-disubstituted aldehydes onto nitroolefins using pyrrolidine–oxyimide catalyst was reported. The reaction works effectively under neat conditions with 15 mol % of catalyst and 10 mol % of p-nitrobenzoic acid as an additive at 0 °C; this results in the formation of Michael adducts possessing an all-carbon quaternary center with good yields and

  报道了使用吡咯烷-氧酰亚胺催化剂将α，α-二取代醛有机催化对映选择性迈克尔加成到硝基烯烃上。该反应在纯净条件下在0°C下以15 mol％的催化剂和10 mol％的对硝基苯甲酸为添加剂可有效地进行；这导致形成具有全碳四元中心并具有良好收率和对映选择性的迈克尔加合物。
• Enantioselective Michael addition of aldehydes to nitroolefins catalyzed by pyrrolidine-HOBt
  作者：Togapur Pavan Kumar、Mohammad Abdul Sattar、Sthanikam Siva Prasad、Kothapalli Haribabu、Cirandur Suresh Reddy

  DOI：10.1016/j.tetasy.2017.02.005

  日期：2017.3

  The oxytriazole catalyst "pyrrolidine-HOBt" developed for asymmetric Michael addition of cyclohexanone to nitroolefins is now evaluated for the asymmetric Michael addition of aldehydes to nitroolefins under similar reaction conditions. The results of this study indicate that, the oxytriazole catalyst "pyrrolidine-HOBt" is equally effective in promoting the Michael addition of aldehydes to nitroolefins on employing benzoic acid as an additive. The desired products, gamma-nitrocarbonyl compounds were obtained in good yields and high enantioselectivities. (C) 2017 Elsevier Ltd. All rights reserved.