2-(2-methylpropyl)-3-oxazoline | 1383625-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(2-methylpropyl)-3-oxazoline
• 英文别名: 2-isobutyl-3-oxazoline；2-(2-Methylpropyl)-2,5-dihydro-1,3-oxazole；2-(2-methylpropyl)-2,5-dihydro-1,3-oxazole
• CAS: 1383625-88-4
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: PHFHTSLUMSGATL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-isobutyl-3-oxazolidine 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(2-methylpropyl)-3-oxazoline
  参考文献：
  名称：

  New Insights into the Formation of Aroma-Active Strecker Aldehydes from 3-Oxazolines as Transient Intermediates

  摘要：

  2-Substituted-5-methyl-3-oxazolines, a novel class of aroma precursors that are able to release the respective Strecker aldehydes by hydrolysis, were identified. Hydrolysis can take place after the addition of water or with human saliva during mastication, respectively. 2-Isobutyl-, 2-sec-isobutyl-, 2-isopropyl, and 2-benzyl-5-methyl-3-oxazolines were synthesized and structurally identified by means of gas chromatography-mass spectrometry (GC-MS) in the electron impact mode and in the chemical ionization mode as well as by one- and two-dimensional NMR experiments. With these compounds at hand, a variety of stability experiments were performed using headspace-GC-MS or proton transfer reaction-MS techniques on the basis of stable isotope dilution assays, proving the ability to release the respective Strecker aldehydes was dependent on the pH value as well as on the hydrolysis time. After the addition of water at 37 degrees C, for example, >70 mol % of 3-methylbutanal or >40 mol % of phenylacetaldehyde was liberated from a solution of 2-isobutyl-5-methyl-3-oxazoline or 2-benzyl-5-methyl-3-oxazoline, respectively, after 5 min. Furthermore, the presence of 2-isobutyl-5-methyl-3-oxazoline in dark chocolate containing 70% cocoa was proven by GC-MS.

  DOI：

  10.1021/jf301489j

文献信息

• [EN] USE OF OXAZOLINES AS AROMA/FLAVOUR PRECURSORS<br/>[FR] UTILISATION D'OXAZOLINES COMME PRÉCURSEURS D'ARÔME/DE SAVEUR
  申请人：NESTEC SA

  公开号：WO2013143904A1

  公开（公告）日：2013-10-03

  The present invention relates to compounds based on an oxazoline moiety which liberate Strecker aldehydes under mild and controllable conditions. In addition the invention relates to food products comprising such compounds, and uses of such compounds.

  本发明涉及基于噁唑啉基团的化合物，该化合物在温和和可控条件下释放 Strecker 醛。此外，该发明涉及包含这种化合物的食品产品，以及这种化合物的用途。
• Use of oxazolines as aroma/flavour precursors
  申请人：Nestec S.A.

  公开号：EP2644602A1

  公开（公告）日：2013-10-02

  The present invention relates to compounds based on an oxazoline moiety which liberate Strecker aldehydes under mild and controllable conditions. In addition the invention relates to food products comprising such compounds, and uses of such compounds.

  本发明涉及基于噁唑烷基团的化合物，在温和和可控条件下释放Strecker醛的方法。此外，本发明涉及包含此类化合物的食品产品以及此类化合物的用途。
• USE OF OXAZOLINES AS AROMA/FLAVOUR PRECURSORS
  申请人：Nestec S.A.

  公开号：EP2831051B1

  公开（公告）日：2017-03-01
• New Insights into the Formation of Aroma-Active Strecker Aldehydes from 3-Oxazolines as Transient Intermediates
  作者：Michael Granvogl、Ersan Beksan、Peter Schieberle

  DOI：10.1021/jf301489j

  日期：2012.6.27

  2-Substituted-5-methyl-3-oxazolines, a novel class of aroma precursors that are able to release the respective Strecker aldehydes by hydrolysis, were identified. Hydrolysis can take place after the addition of water or with human saliva during mastication, respectively. 2-Isobutyl-, 2-sec-isobutyl-, 2-isopropyl, and 2-benzyl-5-methyl-3-oxazolines were synthesized and structurally identified by means of gas chromatography-mass spectrometry (GC-MS) in the electron impact mode and in the chemical ionization mode as well as by one- and two-dimensional NMR experiments. With these compounds at hand, a variety of stability experiments were performed using headspace-GC-MS or proton transfer reaction-MS techniques on the basis of stable isotope dilution assays, proving the ability to release the respective Strecker aldehydes was dependent on the pH value as well as on the hydrolysis time. After the addition of water at 37 degrees C, for example, >70 mol % of 3-methylbutanal or >40 mol % of phenylacetaldehyde was liberated from a solution of 2-isobutyl-5-methyl-3-oxazoline or 2-benzyl-5-methyl-3-oxazoline, respectively, after 5 min. Furthermore, the presence of 2-isobutyl-5-methyl-3-oxazoline in dark chocolate containing 70% cocoa was proven by GC-MS.