2-bromo-4-methylpentanamide | 251366-29-7

• 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: 2-bromo-4-methylpentanamide
• 英文别名: 2-bromo-4-methyl-valeric acid amide；2-Brom-4-methyl-valeriansaeure-amid；Bromisocapronsaureamid
• CAS: 251366-29-7
• 化学式: C₆H₁₂BrNO
• 分子量: 194.071
• InChiKey: DXPIXFMCCPYFES-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  261.6±23.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  DL-亮氨酸 在 ammonium hydroxide 、 氯化亚砜 、 氢溴酸 、 N,N-二甲基甲酰胺 、 potassium bromide 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-bromo-4-methylpentanamide
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched α-Bromonitriles from Amino Acids

  摘要：

  Two methods were investigated for the preparation of six chiral alpha-bromonitriles with different optic purities. The nitrous deamination of amino acids gives alpha-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford alpha-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding alpha-bromoamids using thionyl chloride gives alpha-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.

  DOI：

  10.1080/00397911.2011.608142

文献信息

• 1-(3,4,5-Trimethoxycinnamoyl)-4-aminocarbonylethyl-substituted piperazine derivatives and a process for the preparation thereof
  申请人：Hokuriku Pharmaceutical Co.,Ltd

  公开号：EP0083712A1

  公开（公告）日：1983-07-20

  1-(3,4,5-Trimethoxycinnamoyl)-4-aminocarbonylethyl-substituted piperazine derivatives represented by general formula (I): wherein R is a straight- or branched-chain alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 7 carbon atoms, and pharmaceutically acceptable acid addition salts thereof are disclosed. The 1-(3,4,5-trimethoxycinnamoyl)-4-aminocarbonylethyl-substituted piperazine derivatives are useful as vasodilator agents.

  1-(3,4,5-三甲氧基肉桂酰基)-4-氨基羰基乙基取代的哌嗪衍生物由通式(I)代表：其中R是具有1至6个碳原子的直链或支链烷基或具有5至7个碳原子的环烷基，以及其药学上可接受的酸加成盐被公开。 1-(3,4,5-三甲氧基肉桂酰基)-4-氨基羰基乙基取代的哌嗪衍生物可用作血管扩张剂。
• Bergell; Wuelfing, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1910, vol. 64, p. 360
  作者：Bergell、Wuelfing

  DOI：——

  日期：——
• US6358971B1
  申请人：——

  公开号：US6358971B1

  公开（公告）日：2002-03-19
• [EN] IMPROVED SYNTHESIS OF OPTICALLY PURE (S) - 3-CYANO-5-METHYL-HEXANOIC ACID ALKYL ESTER, AN INTERMEDIATE OF (S)- PREGABALIN<br/>[FR] SYNTHÈSE AMÉLIORÉE D'UN ESTER ALKYLIQUE OPTIQUEMENT PUR DE L'ACIDE (S) - 3-CYANO-5-MÉTHYL-HEXANOÏQUE, INTERMÉDIAIRE DE LA (S)-PRÉGABALINE
  申请人：LUPIN LTD

  公开号：WO2011141923A2

  公开（公告）日：2011-11-17

  The present invention is directed towards synthesis of (S) - 3-cyano-5-methyl-hexanoic acid ethyl ester. A cost effective, eco-friendly process for preparation of enantiomerically pure (S)-3-cyano-5-methyl-hexanoic acid alkyl ester, intermediate of γ-amino acids, particularly (S)-pregabalin.