(S)-2-(4-cyanophenyl)-1-nitropropane

• 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)-2-(4-cyanophenyl)-1-nitropropane
• 英文别名: 4-[(2S)-1-nitropropan-2-yl]benzonitrile
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: XFXCEMAMUGIAFS-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氰基苯乙酮 在 chiral thiourea derivative 二氢吡啶 、 正丁胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (S)-2-(4-cyanophenyl)-1-nitropropane
  参考文献：
  名称：

  Organocatalytic Asymmetric Transfer Hydrogenation of Nitroolefins

  摘要：

  We describe a highly efficient and highly enantioselective Hantzsch ester mediated conjugate transfer hydrogenation of beta,beta-disubstituted nitroolefins that is catalyzed by a Jacobsen-type thiourea catalyst.

  DOI：

  10.1021/ja074045c

文献信息

• Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins
  作者：Jakob F. Schneider、Markus B. Lauber、Vanessa Muhr、Domenic Kratzer、Jan Paradies

  DOI：10.1039/c1ob05059a

  日期：——

  focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action

  本文着重于易于访问的内容 硫脲衍生自氨基酸的氢键催化剂，其位阻和电子特征受其在甲醇碳中心的取代度的调节。这些催化剂被用于硝基烯烃的不对称转移氢化，从而以高达99％的收率和86％的对映体过量提供手性产物。所提出的催化剂的作用方式得到机理研究的支持。
• Enantioselective iridium-catalyzed hydrogenation of β,β-disubstituted nitroalkenes
  作者：Yan-Bo Yu、Lei Cheng、Yi-Pan Li、Yue Fu、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1039/c6cc01273f

  日期：——

  An iridium complex with a newly prepared chiral spiro amino-phosphine ligand efficiently catalyzed the hydrogenation of both [small beta]-aryl-[small beta]-methyl-nitroalkenes and [small beta]-alkyl-[small beta]-methyl-nitroalkenes to the corresponding saturated nitroalkanes, which represents the first report...

  具有新制备的手性螺氨基氨基膦配体的铱络合物有效地催化了β-芳基-β-甲基-硝基硝基和β-烷基-β-甲基-硝基硝基的小氢化。到相应的饱和硝基烷烃，这是第一个报告。
• Organocatalytic Asymmetric Transfer Hydrogenation of Nitroolefins
  作者：Nolwenn J. A. Martin、Lidia Ozores、Benjamin List

  DOI：10.1021/ja074045c

  日期：2007.7.1

  We describe a highly efficient and highly enantioselective Hantzsch ester mediated conjugate transfer hydrogenation of beta,beta-disubstituted nitroolefins that is catalyzed by a Jacobsen-type thiourea catalyst.