3-bromo-5-butyl-4,5-dihydro-isoxazole | 110164-81-3

• 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: 3-bromo-5-butyl-4,5-dihydro-isoxazole
• 英文别名: Kqkfjvlyvmqpbr-uhfffaoysa-；3-bromo-5-butyl-4,5-dihydro-1,2-oxazole
• CAS: 110164-81-3
• 化学式: C₇H₁₂BrNO
• 分子量: 206.082
• InChiKey: KQKFJVLYVMQPBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  3-bromo-5-butyl-4,5-dihydro-isoxazole 在 镍 lithium methanolate 、 氢气 、 硼酸 作用下， 生成 methyl 3-hydroxyheptanoate
  参考文献：
  名称：

  异恶唑啉向β-羟基酯的转化。2-脱氧-D-核糖的合成

  摘要：

  使用3-溴异恶唑啉作为关键中间体，开发了一种简单有效的具有明确立体化学的β-羟基酯的制备方法。还报道了2-癸基-D-核糖的合成

  DOI：

  10.1016/s0040-4039(00)85028-5
• 作为产物：
  描述：

  1-己烯 、 1,1-二溴甲醛肟 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 以78%的产率得到3-bromo-5-butyl-4,5-dihydro-isoxazole
  参考文献：
  名称：

  异恶唑啉向β-羟基酯的转化。2-脱氧-D-核糖的合成

  摘要：

  使用3-溴异恶唑啉作为关键中间体，开发了一种简单有效的具有明确立体化学的β-羟基酯的制备方法。还报道了2-癸基-D-核糖的合成

  DOI：

  10.1016/s0040-4039(00)85028-5

文献信息

• A New Method for the Preparation of β-Hydroxy Nitriles: Transformation of 3-Bromo-2-isoxazolines to β-Hydroxy Nitriles by Treatment of Alkanethiolates
  作者：Min Hyo Seo、Youn Young Lee、Yang Mo Goo

  DOI：10.1080/00397919408011747

  日期：1994.5

  Abstract 3-Bromo-2-isoxazolines are transformed to β-hydroxy nitriles in good yields by treatment with alkanethiolates under a very mild condition.

  摘要 3-Bromo-2-isoxazolines 通过在非常温和的条件下用链烷硫醇处理以良好的产率转化为 β-羟基腈。
• Synthesis of 3-Aminoisoxazoles via the Addition−Elimination of Amines on 3-Bromoisoxazolines
  作者：Mélina Girardin、Pamela G. Alsabeh、Sophie Lauzon、Sarah J. Dolman、Stéphane G. Ouellet、Greg Hughes

  DOI：10.1021/ol9000284

  日期：2009.3.5

  A novel two-step procedure for the synthesis of 3-amino-5-substituted-isoxazoles Is described. In the presence of a base, readily available 3-bromoisoxazolines react with amines to afford 3-aminoisoxazolines. An oxidation protocol was developed for these heterocycles to provide 3-aminoisoxazoles in consistently high yield.
• Nitrile oxides in medicinal chemistry-2. synthesis of the two enantiomers of dihydromuscimol
  作者：Marco De Amici、Carlo De Micheli、Valeria Misani

  DOI：10.1016/s0040-4020(01)89765-9

  日期：1990.1
• Ring Opening of 3‐Bromo‐2‐Isoxazolines to β‐Hydroxy Nitriles
  作者：Martin G. Kociolek、Kyle P. Kalbarczyk

  DOI：10.1081/scc-200039452

  日期：2004.12.31

  3-Bromo-2-isoxazolines were converted to the corresponding beta-hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para-toluenesulfonic acid. Both methods gave beta-hydroxy nitriles under relatively mild conditions in good to moderate yields for a variety of substituted 3-bromo-2-isoxazolines.
• Nitrile oxides in medicinal chemistry. 4. Chemoenzymic synthesis of chiral heterocyclic derivatives
  作者：Marco De Amici、Paolo Magri、Carlo De Micheli、Francesca Cateni、Roberto Bovara、Giacomo Carrea、Sergio Riva、Gianluigi Casalone

  DOI：10.1021/jo00036a013

  日期：1992.5

  The two enantiomers of 3-bromo-5-(hydroxymethyl)-DELTA-2-isoxazoline (1) and 2-phenyl-5-(hydroxymethyl)-isoxazolidin-3-one (9) have been prepared in enantiomeric excess higher than 90% by hydrolysis of the corresponding butyrates under the catalysis of lipase PS, which was the most selective catalyst of the enzymes tested. The pairs of enantiomers of 1 and 9 were transformed into the chiral forms of the potent muscarinic ligands 3 and 5. The results obtained with the homogeneous set of esters 6, 7, 10a-d evidence a strong dependence of reaction rate and enantioselectivity of the lipase PS-catalyzed transformations upon both the size of the acyl moiety and the shape of the group carrying the alcoholic part of the ester. In the series of esters 10a-d, the best results were obtained with butyrate 10b. Quite interestingly, on passing from the butyrate of 1 to that of 9, the value of the enantiomeric ratio remained remarkably high but the enantiopreference switched from R to S. In between lies the butyrate of 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one [(+/-)-6] which was barely recognized by lipase PS and yielded alcohol (R)-(-)-2 in a modest enantiomeric excess.