anti-2-(hydroxy(4-methylphenyl)methyl)butanenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: anti-2-(hydroxy(4-methylphenyl)methyl)butanenitrile
• 英文别名: (S*)-2-((S*)-hydroxy(p-tolyl)methyl)butanenitrile；(2R)-2-[(R)-hydroxy-(4-methylphenyl)methyl]butanenitrile
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: YYUPYTFQIGJEKN-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  anti-2-(hydroxy(4-methylphenyl)methyl)butanenitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (5R,6R)-5-ethyl-6-(4-methylphenyl)-1,3-oxazinan-2-one
  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
• 作为产物：
  描述：

  乙醇 、 对甲苯酰乙腈 在 4-d-old growing cells of fungus Curvularia lunata CECT 2130 作用下， 生成 anti-2-(hydroxy(4-methylphenyl)methyl)butanenitrile 、 (2S,1'S)-2-[1-hydroxy-1-(4-methylphenyl)methyl]butanenitrile 、 (rel-2R,1'S)-2-[1-hydroxy-1-(4-methylphenyl)methyl]butanenitrile
  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