(2R,3S)-2-ethyl-4-nitro-3-(3-methoxyphenyl)butanal | 1192052-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3S)-2-ethyl-4-nitro-3-(3-methoxyphenyl)butanal
• 英文别名: (2R,3S)-2-ethyl-3-(3-methoxyphenyl)-4-nitrobutanal
• CAS: 1192052-91-7
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: VDNIZTXBBTVPAD-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-methoxy-3-(2-nitro-vinyl)-benzene 、 正丁醛 在 C₁₅H₂₁N₃O₂ 、 S-1,1'-联-2-萘酚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到(2R,3S)-2-ethyl-4-nitro-3-(3-methoxyphenyl)butanal
  参考文献：
  名称：

  Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by l-prolinamide derivatives using phenols as co-catalysts

  摘要：

  The asymmetric Michael addition of aldehydes to nitroolefins was investigated using L-prolinamide derivatives of 2-(2'-piperidinyl)pyridine as catalyst and a variety of phenols as co-catalyst. Extensive screening toward the effect of prolinamides, phenols, and solvents on this transformation revealed that a combination of (S)-2-(2'-piperidinyl)pyridine-derived trans-4-hydroxy-L-prolinamide 2c, (S)-1,1'-bi-2-naphthol, and dichloromethane was a promising system. This system was shown to be amenable to a rich variety of aldehydes and nitroolefins and afforded the nitroaldehyde products with excellent yield, enantiomeric excess (up to 99%) and diastereoselectivity ratio (up to 99/1), even in the case of 1 mol % catalyst loading and 1.5 equiv of aldehydes. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.022

文献信息

• Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by l-prolinamide derivatives using phenols as co-catalysts
  作者：Yan-Qin Cheng、Zheng Bian、Ya-Bing He、Fu-She Han、Chuan-Qing Kang、Zhao-Lun Ning、Lian-Xun Gao

  DOI：10.1016/j.tetasy.2009.07.022

  日期：2009.8

  The asymmetric Michael addition of aldehydes to nitroolefins was investigated using L-prolinamide derivatives of 2-(2'-piperidinyl)pyridine as catalyst and a variety of phenols as co-catalyst. Extensive screening toward the effect of prolinamides, phenols, and solvents on this transformation revealed that a combination of (S)-2-(2'-piperidinyl)pyridine-derived trans-4-hydroxy-L-prolinamide 2c, (S)-1,1'-bi-2-naphthol, and dichloromethane was a promising system. This system was shown to be amenable to a rich variety of aldehydes and nitroolefins and afforded the nitroaldehyde products with excellent yield, enantiomeric excess (up to 99%) and diastereoselectivity ratio (up to 99/1), even in the case of 1 mol % catalyst loading and 1.5 equiv of aldehydes. (c) 2009 Elsevier Ltd. All rights reserved.