(S)-1-(2-nitro-1-p-tolylethyl)cyclopentanecarbaldehyde | 1426836-18-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-1-(2-nitro-1-p-tolylethyl)cyclopentanecarbaldehyde
• CAS: 1426836-18-1
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: VDAIBCGYGBJINE-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  环戊基甲醛 、 (E)-2-(4-methylphenyl)-1-nitroethene 在 1-[(1S,2S)-2-aminocyclohexyl]-3-[3-[[27-[3-[[(1S,2S)-2-aminocyclohexyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea 作用下， 以 二氯甲烷 为溶剂， 反应 108.0h， 以77%的产率得到(S)-1-(2-nitro-1-p-tolylethyl)cyclopentanecarbaldehyde
  参考文献：
  名称：

  基于杯芳烃的高效伯胺-硫脲有机催化剂用于醛与硝基苯乙烯的不对称迈克尔加成

  摘要：

  首次描述了从对叔丁基杯[4]芳烃合成基于杯[4]芳烃的手性双功能伯胺-硫脲催化剂。杯[4]芳烃基催化剂被成功应用于促进醛与硝基烯烃的迈克尔加成，优先提供（R）-或（S）-加合物的高产率（高达95%）和优异的对映选择性（高达99%） es）。

  DOI：

  10.1080/10610278.2013.773331

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。
• 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.