(2R,1'R)-2-(1-hydroxy-1-phenylmethyl)hexanenitrile | 264229-61-0

• 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: (2R,1'R)-2-(1-hydroxy-1-phenylmethyl)hexanenitrile
• 英文别名: (2R)-2-[(R)-hydroxy(phenyl)methyl]hexanenitrile
• CAS: 264229-61-0
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: QXFAFAUAOYNZHC-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (2R,1'R)-2-(1-hydroxy-1-phenylmethyl)hexanenitrile 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-butyl-6-phenyl-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：

  苯甲酰乙腈 、 正丁醇 在 4-d-old growing cells of fungus Curvularia lunata CECT 2130 作用下， 生成 (2R,1'R)-2-(1-hydroxy-1-phenylmethyl)hexanenitrile 、 (2S,1'S)-2-(1-hydroxy-1-phenylmethyl)hexanenitrile 、 (rel-2R,1'S)-2-(1-hydroxy-1-phenylmethyl)hexanenitrile
  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

• Biotransformations of benzoylacetonitrile with the fungus Curvularia lunata: highly diastereo- and enantioselective synthesis of α-alkyl β-hydroxy nitriles and γ-amino alcohols
  作者：Vicente Gotor、Juan R. Dehli、Francisca Rebolledo

  DOI：10.1039/a909721j

  日期：——

  Incubation of alcoholic solutions of benzoylacetonitrile, 1, with a suitable aqueous culture of C. lunata results in highly diastereo- and enantioselective reactions leading to α-alkyl β-hydroxy nitriles 3, which are easily reduced to the corresponding γ-amino alcohols 6.

  将苯乙酰腈的酒精溶液与适当的C. lunata水相培养物共同孵育，会导致高度的非对映体选择性和对映体选择性反应，生成α-烷基β-羟基腈3，这些化合物可以方便地还原为相应的γ-氨基醇6。