(R)-(-)-3-nitromethyl-4-phenylbutanoic acid | 1039497-60-3

• 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: (R)-(-)-3-nitromethyl-4-phenylbutanoic acid
• 英文别名: (3R)-3-benzyl-4-nitrobutanoic acid
• CAS: 1039497-60-3
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: SAGTULLNOZRMQR-SNVBAGLBSA-N

物化性质

• 沸点：
  402.6±38.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-nitromethyl-4-phenylbutanoic acid 以 phosphate buffer 为溶剂， 生成 R-2-苄基琥珀酸
  参考文献：
  名称：

  A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

  摘要：

  Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main Compounds of interest involved are given, together with their CD spectra. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.014
• 作为产物：
  描述：

  ethyl 3-nitromethyl-4-phenylbutanoate 在 potassium dihydrogenphosphate 、 sodium phosphate 、 α-chymotrypsin 作用下， 以 水 为溶剂， 反应 15.0h， 生成 (R)-(-)-3-nitromethyl-4-phenylbutanoic acid 、 (S)-(+)-3-nitromethyl-4-phenylbutanoic acid
  参考文献：
  名称：

  A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

  摘要：

  Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main Compounds of interest involved are given, together with their CD spectra. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.014

文献信息

• A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin
  作者：Fulvia Felluga、Giuliana Pitacco、Ennio Valentin、Cesare Daniele Venneri

  DOI：10.1016/j.tetasy.2008.03.014

  日期：2008.5

  Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main Compounds of interest involved are given, together with their CD spectra. (C) 2008 Elsevier Ltd. All rights reserved.