ethyl (R)-(-)-3-(nitromethyl)heptanoate | 1039497-31-8

• 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: ethyl (R)-(-)-3-(nitromethyl)heptanoate
• 英文别名: ethyl (3R)-3-(nitromethyl)heptanoate
• CAS: 1039497-31-8
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: CJCKANNWBYPUFI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  ethyl (R)-(-)-3-(nitromethyl)heptanoate 在 镍 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 以70%的产率得到(R)-(+)-4-butyl-2-pyrrolidinone
  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)heptanoate 在 potassium dihydrogenphosphate 、 Novozym 435 Candida antarctica lipase B 、 sodium phosphate 作用下， 以 水 为溶剂， 反应 3.0h， 以21%的产率得到ethyl (R)-(-)-3-(nitromethyl)heptanoate
  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.