2-isobutyl-3-oxazolidine | 51995-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-isobutyl-3-oxazolidine
• 英文别名: 2-(2-Methylpropyl)-1,3-oxazolidine
• CAS: 51995-39-2
• 化学式: C₇H₁₅NO
• 分子量: 129.202
• InChiKey: YGRAOGDVKXUBJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  C.I.酸性橙108 、 异戊醛 在 4 A molecular sieve 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2-isobutyl-3-oxazolidine
  参考文献：
  名称：

  Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives

  摘要：

  A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.

  DOI：

  10.1021/jo062626z

文献信息

• 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。
• N-acylamino acid derivatives and their use
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0309766A2

  公开（公告）日：1989-04-05

  An N-acylamino acid derivative of the formula: wherein each of R¹, R², R⁴ and R⁶ is hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl or a monocyclic or bicyclic heterocyclic group containing from 1 to 4 hetero atoms; each of R³ and R⁵ is hydrogen or lower alkyl; A is -CH(OH)-(CH₂)qR⁷ wherein R⁷ is hydrogen, lower alkyl, cycloalkyl, cyloalkylalkyl, aryl, aralkyl, a monocyclic or bicyclic heterocyclic group containing from 1 to 4 hetero atoms or -E-R¹⁰ wherein E is -S(O)i- wherein i is 0, 1 or 2, oxygen, -NR¹¹- wherein R¹¹ is hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, or wherein each of R¹² and R¹³ is hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, and R¹⁰ is hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl or a monocyclic or bicyclic heterocyclic group containing from 1 to 4 hetero atoms provided that when R¹⁰ is hydrogen, i is 0, and q is an integer of from 0 to 5; or -CH₂-CHR⁸-CO-R⁹ wherein R⁸ is hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl or a monocyclic or bicyclic heterocyclic group containig from 1 to 4 hetero atoms, and R⁹ is hydroxyl, -OX wherein X is alkyl, aryl, lower alkoxycarbonyloxyalkyl or 1-phthalidyl, or -N(Y¹)(Y²) wherein each of Y¹ and Y² is hydrogen, lower alkyl, aryl, aralkyl or cycloalkyl, or Y¹ and Y² form together with the adjacent nitrogen atom a 5- or 6-membered heterocyclic group which may contain a further hetero atom; m is 0, 1 or 2; and n is an integer of from 1 to 5, provided that when R¹ is hydrogen, m is 0; or a salt thereof, which is useful as hypotensive drugs.

  一种 N-酰基氨基酸衍生物，其式如下 其中 R¹、R²、R⁴ 和 R⁶ 各为氢、低级烷基、环烷基、环烷基烷基、芳基、芳烷基或含有 1 至 4 个杂原子的单环或双环杂环基团；R³ 和 R⁵ 各为氢或低级烷基；A 是 -CH(OH)-(CH₂)qR⁷，其中 R⁷ 是氢、低级烷基、环烷基、环烷基烷基、芳基、芳烷基、含有 1 至 4 个杂原子的单环或双环杂环基团或 -E-R¹⁰ ，其中 E 是 -S(O)i- 其中 i 是 0、1或2、氧、-NR¹¹- 其中R¹¹是氢、低级烷基、环烷基、环烷基烷基、芳基或芳烷基，或 其中 R¹² 和 R¹³ 均为氢、低级烷基、环烷基、环烷基烷基、芳基或芳烷基，且 R¹⁰ 为氢、低级烷基、环烷基、环烷基烷基、芳基、芳烷基或含有 1 至 4 个杂质原子的单环或双环杂环基团，但当 R¹⁰ 为氢时，i 为 0，q 为 0 至 5 的整数；或-CH₂-CHR⁸-CO-R⁹，其中 R⁸ 是氢、低级烷基、环烷基、环烷基烷基、芳基、芳烷基或含有 1 至 4 个杂原子的单环或双环杂环基团，且 R𠞙 是羟基、-OX，其中 X 是烷基、芳基、或-N(Y¹)(Y²)，其中 Y¹ 和 Y² 分别为氢、低级烷基、芳基、芳烷基或环烷基，或 Y¹ 和 Y² 与邻近的氮原子一起形成 5 或 6 元杂环基团，该杂环基团可能含有另一个杂原子；m为0、1或2；n为1至5的整数，但当R¹为氢时，m为0；或其盐，可用作降血压药物。
• Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives
  作者：Luca Banfi、Andrea Basso、Giuseppe Guanti、Nicola Kielland、Claudio Repetto、Renata Riva

  DOI：10.1021/jo062626z

  日期：2007.3.1

  A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.
• 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.