2-ethyl-3-hydroxybutyronitrile | 38046-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethyl-3-hydroxybutyronitrile
• 英文别名: Butanenitrile, 2-ethyl-3-hydroxy-；2-ethyl-3-hydroxybutanenitrile
• CAS: 38046-53-6
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: MKLDCYVWGCYGDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氰基丙酮 、 乙醇 在 4-d-old growing cells of fungus Curvularia lunata CECT 2130 作用下， 生成 2-ethyl-3-hydroxybutyronitrile
  参考文献：
  名称：

  Stereoselective alkylation–reduction of β-keto nitriles by the fungus Curvularia lunata

  摘要：

  The alkylation-reduction (AR) reaction of beta -keto nitriles by growing cells of Curvularia lunata CECT 2130 has been explored. The reaction conditions for the ethylation of benzoylacetonitrile have been optimized in terms of both yield and stereoselectivity and the mechanism of this biotransformation vas studied. The scope of this reaction has been extended to other alkylations (R = Et, Pr, Bu, iso-Bu) and to a series of aromatic and heteroaromatic substrates, yielding the corresponding optically active alpha -alkyl beta -hydroxy nitrites. The yield (directly related to competing carbonyl reduction reaction) depends on the substrate bulk. whereas the enantiomeric and diastereomeric excesses (both up to 98%) seem to be dependent on several Factors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00269-5

文献信息

• Sur les zinciques issus des α-bromonitriles
  作者：Nicole Goasdoué、Marcel Gaudemar

  DOI：10.1016/s0022-328x(00)88900-7

  日期：1972.6

  Organozinc compounds derived from α-bromonitriles are readily prepared in solution in tetrahydrofuran (THF) and exist in the C metallated form. They condense normally with aldehydes and saturated ketones. A number of new β-hydroxy-nitriles are described. The addition of conjugated unsaturated ketones results in the formation of β-hydroxynitriles or ketonitriles, depending on the nature of the initial

  衍生自α-溴腈的有机锌化合物很容易在四氢呋喃（THF）中制成溶液，并以C金属化形式存在。它们通常与醛和饱和酮缩合。描述了许多新的β-羟基腈。取决于初始溴腈的性质，共轭不饱和酮的添加导致形成β-羟基腈或酮腈。苯甲醛与锌-α-溴腈的反应的立体化学不受溶剂性质的影响。与丙二酸二乙酯亚烷基的缩合产生预期的1，4-加成产物。
• Stereoselective alkylation–reduction of β-keto nitriles by the fungus Curvularia lunata
  作者：Juan R. Dehli、Vicente Gotor

  DOI：10.1016/s0957-4166(01)00269-5

  日期：2001.6

  The alkylation-reduction (AR) reaction of beta -keto nitriles by growing cells of Curvularia lunata CECT 2130 has been explored. The reaction conditions for the ethylation of benzoylacetonitrile have been optimized in terms of both yield and stereoselectivity and the mechanism of this biotransformation vas studied. The scope of this reaction has been extended to other alkylations (R = Et, Pr, Bu, iso-Bu) and to a series of aromatic and heteroaromatic substrates, yielding the corresponding optically active alpha -alkyl beta -hydroxy nitrites. The yield (directly related to competing carbonyl reduction reaction) depends on the substrate bulk. whereas the enantiomeric and diastereomeric excesses (both up to 98%) seem to be dependent on several Factors. (C) 2001 Elsevier Science Ltd. All rights reserved.