(R)-(-)-5-methyl-3-(nitromethyl)hexanoic acid | 181289-44-1

• 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)-(-)-5-methyl-3-(nitromethyl)hexanoic acid
• 英文别名: (3R)-5-methyl-3-(nitromethyl)hexanoic acid
• CAS: 181289-44-1
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: DTIRCYURNGJGSY-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methyl-1-(3-methyl-4-nitro-isoxazol-5-yl)-pentan-2-ol 在 N-[3,5-bis(trifluoromethyl)benzyl]cinchonidium bromide 、 potassium carbonate 、 甲基磺酰氯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 56.5h， 生成 (R)-(-)-5-methyl-3-(nitromethyl)hexanoic acid
  参考文献：
  名称：

  制备3-甲基-4-硝基亚烷基乙基异恶唑的改进方法及其在硝基甲烷催化对映选择性迈克尔加成反应中的反应†

  摘要：

  在这里，我们描述了3-甲基-4-硝基-5-烷基乙烯基异恶唑的简短合成及其作为迈克尔受体的反应性。在相转移催化下，标题化合物与硝基甲烷反应，得到高度对映体富集的加合物（最高93％ee），然后将其转化为相应的γ-硝酸。

  DOI：

  10.1039/c4ob02109f

文献信息

• [EN] METHOD FOR THE PREPARATION OF BETA-SUBSTITUTED GAMMA-AMINO CARBOXYLIC ACIDS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'ACIDES GAMMA-AMINOCARBOXYLIQUES SUBSTITUÉS EN POSITION BÊTA
  申请人：SIEGFRIED LTD

  公开号：WO2015189068A1

  公开（公告）日：2015-12-17

  The present invention relates to the preparation of β-substituted γ-amino carboxylic acids, preferably in enantiomerically enriched or even enantiomerically pure form, by a one-pot conversion of a β-substituted γ-nitro dicarboxylic acid ester or of a β-substituted γ-nitro dicarboxylate of general formula to a β-substituted γ-nitro carboxylic acid and a subsequent reduction of the γ-nitro group to an amine group. In particular, the present invention relates to the preparation of ( S ) -pregabalin. In addition, the formation of enantiomerically enriched β-substituted γ-amino carboxylic acids and β-substituted γ-nitronate carboxylic acid salts are also described.

  本发明涉及通过一锅法将β-取代γ-硝基二羧酸酯或一般式的β-取代γ-硝基二羧酸酯转化为β-取代γ-硝基羧酸，然后将γ-硝基还原为胺基，从而制备β-取代γ-氨基羧酸，优选为对映富集或甚至对映纯形式。特别是，本发明涉及(S)-盐酸普拉巴林的制备。此外，还描述了对映富集的β-取代γ-氨基羧酸和β-取代γ-硝酸盐的形成。
• 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。
• 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.
• 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