ethyl (R)-(-)-5-methyl-3-(nitromethyl)hexanoate | 1039497-37-4

• 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)-(-)-5-methyl-3-(nitromethyl)hexanoate
• 英文别名: ethyl (3R)-5-methyl-3-(nitromethyl)hexanoate
• CAS: 1039497-37-4
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: LOHHVAYLSGONPS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 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)-(-)-5-methyl-3-(nitromethyl)hexanoate 在 镍 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 以81%的产率得到(R)-4-isobutylpyrrolidin-2-one
  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：

  5-甲基-3-(硝基甲基)己酸乙酯 在 potassium dihydrogenphosphate 、 Novozym 435 Candida antarctica lipase B 、 sodium phosphate 作用下， 以 水 为溶剂， 反应 5.0h， 以30%的产率得到ethyl (R)-(-)-5-methyl-3-(nitromethyl)hexanoate
  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

• PROCESS FOR THE STEREOSELECTIVE ENZYMATIC HYDROLYSIS OF 5-METHYL-3-NITROMETHYL-HEXANOIC ACID ESTER
  申请人：Albert Martin

  公开号：US20110165636A1

  公开（公告）日：2011-07-07

  The present invention relates to processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid ester and its salts. Also disclosed are processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid salt and a process for the preparation of 3-(aminomethyl)-5-methylhexanoic acid. (S)-5-Methyl-3-nitromethyl-hexanoic acid or (R)-5-methyl-3-nitromethyl-hexanoic acid in enantioenriched form or enantiopure form as well as salts thereof, (S)-5-methyl-3-nitromethyl-hexanoic acid ester or (R)-5-methyl-3-nitromethyl-hexanoic acid ester in enantioenriched form or enantiopure form and a compound, namely Formula (XIII), in racemic form, enantioenriched form or enantiopure form are also disclosed.

  本发明涉及制备5-甲基-3-硝基甲基己酸酯及其盐的过程。还公开了制备5-甲基-3-硝基甲基己酸盐的过程和制备3-(氨甲基)-5-甲基己酸的过程。本发明还公开了(S)-5-甲基-3-硝基甲基己酸或(R)-5-甲基-3-硝基甲基己酸的对映富集形式或对映纯形式及其盐，(S)-5-甲基-3-硝基甲基己酸酯或(R)-5-甲基-3-硝基甲基己酸酯的对映富集形式或对映纯形式，以及一种化合物，即公式(XIII)，其为外消旋体、对映富集形式或对映纯形式。
• Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
  申请人：Sandoz AG

  公开号：EP2294207B1

  公开（公告）日：2012-09-26
• US8546112B2
  申请人：——

  公开号：US8546112B2

  公开（公告）日：2013-10-01
• [EN] PROCESS FOR THE STEREOSELECTIVE ENZYMATIC HYDROLYSIS OF 5-METHYL-3-NITROMETHYL-HEXANOIC ACID ESTER<br/>[FR] PROCÉDÉ POUR L'HYDROLYSE ENZYMATIQUE STÉRÉOSÉLECTIVE D'UN ESTER D'ACIDE 5-MÉTHYL-3-NITROMÉTHYL-HEXANOÏQUE
  申请人：SANDOZ AG

  公开号：WO2009141362A2

  公开（公告）日：2009-11-26

  The present invention relates to processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid ester and its salts. Also disclosed are processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid salt and a process for the preparation of 3-(aminomethyl)-5- methylhexanoic acid. (S)-5-Methyl-3-nitromethyl-hexanoic acid or (R)-5-methyl-3-nitromethyl-hexanoic acid in enantioenriched form or enantiopure form as well as salts thereof, (S)-5-methyl-3-nitromethyl-hexanoic acid ester or (R)-5-methyl-3-nitromethyl-hexanoic acid ester in enantioenriched form or enantiopure form and a compound, namely Formula (XIII), in racemic form, enantioenriched form or enantiopure form are also disclosed.
• 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.