(S)-2-ethyl-3-nitropropionic acid methyl ester | 538376-63-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-ethyl-3-nitropropionic acid methyl ester
• 英文别名: methyl (2S)-2-(nitromethyl)butanoate
• CAS: 538376-63-5
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: XVHXDYYTFGOQHT-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-ethyl-3-nitropropionic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 生成 (S)-2-Aminomethyl-butyric acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β2-amino acids by Michael addition of diorgano zinc reagents to nitro acrylates

  摘要：

  Phosphoramidite-derived copper(I) catalysts readily facilitate the enantioselective 1,4-addition of dialkyl zinc reagents to nitro acrylates. The resulting 2-substituted 3-nitro propionic acid esters can easily be transformed to beta(2)-amino acids. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00788-7
• 作为产物：
  描述：

  methyl (E)-3-nitroacrylate 、 三乙基铝 在 diethylzinc 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 生成 (R)-2-ethyl-3-nitropropionic acid methyl ester 、 (S)-2-ethyl-3-nitropropionic acid methyl ester
  参考文献：
  名称：

  Stereoselective Michael addition of trimethyl aluminium to nitro acrylates: a route to 2-methyl-3-amino propionic acid

  摘要：

  The copper(I)-catalysed Michael addition of trimethyl aluminium to nitro acrylates yields 2-methyl-3-nitro propionic acid esters on a 200 g scale with enantiomeric excesses up to 92%. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00575-5

文献信息

• Stereoselective Michael addition of trimethyl aluminium to nitro acrylates: a route to 2-methyl-3-amino propionic acid
  作者：Uwe Eilitz、Frank Leßmann、Oliver Seidelmann、Volkmar Wendisch

  DOI：10.1016/s0957-4166(03)00575-5

  日期：2003.10

  The copper(I)-catalysed Michael addition of trimethyl aluminium to nitro acrylates yields 2-methyl-3-nitro propionic acid esters on a 200 g scale with enantiomeric excesses up to 92%. (C) 2003 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of β2-amino acids by Michael addition of diorgano zinc reagents to nitro acrylates
  作者：Uwe Eilitz、Frank Leßmann、Oliver Seidelmann、Volkmar Wendisch

  DOI：10.1016/s0957-4166(02)00788-7

  日期：2003.1

  Phosphoramidite-derived copper(I) catalysts readily facilitate the enantioselective 1,4-addition of dialkyl zinc reagents to nitro acrylates. The resulting 2-substituted 3-nitro propionic acid esters can easily be transformed to beta(2)-amino acids. (C) 2003 Elsevier Science Ltd. All rights reserved.