(2R,1'R)-2-[1-(2-furyl)-1-hydroxymethyl]butanenitrile | 366814-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2R,1'R)-2-[1-(2-furyl)-1-hydroxymethyl]butanenitrile
• 英文别名: (2R)-2-[(R)-furan-2-yl(hydroxy)methyl]butanenitrile
• CAS: 366814-81-5
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: HODQKUQHFKXVOR-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,1'R)-2-[1-(2-furyl)-1-hydroxymethyl]butanenitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (1R,2R)-2-Aminomethyl-1-furan-2-yl-butan-1-ol
  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：

  3-(furan-2-yl)-2-methyl-3-oxo-butannitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (2R,1'R)-2-[1-(2-furyl)-1-hydroxymethyl]butanenitrile 、 2-(furan-2-yl(hydroxyl)methyl)butanenitrile
  参考文献：
  名称：

  Efficient methodology to produce a duloxetine precursor using whole cells of Rhodotorula rubra

  摘要：

  Different types of yeasts were employed as biocatalysts in the reduction of beta-ketonitriles. The red microorganism, Rhodotorula rubra, was selected as the best performing catalyst in the reduction of different substituted ketonitriles giving total stereoselectivity in most cases (90-99% ee). In particular, its use as fresh and lyophilised cells was expanded to a semi-preparative scale for the production of the duloxetine precursor 1a, R. rubra was screened in the reduction of alkylation products in comparison with Pichia henricii for assignment of configuration of products 2a and 11a after derivatisation with S-MPA. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2016.04.002

文献信息

• 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.
• Efficient methodology to produce a duloxetine precursor using whole cells of Rhodotorula rubra
  作者：Isabella Rimoldi、Giorgio Facchetti、Donatella Nava、Martina Letizia Contente、Raffella Gandolfi

  DOI：10.1016/j.tetasy.2016.04.002

  日期：2016.6

  Different types of yeasts were employed as biocatalysts in the reduction of beta-ketonitriles. The red microorganism, Rhodotorula rubra, was selected as the best performing catalyst in the reduction of different substituted ketonitriles giving total stereoselectivity in most cases (90-99% ee). In particular, its use as fresh and lyophilised cells was expanded to a semi-preparative scale for the production of the duloxetine precursor 1a, R. rubra was screened in the reduction of alkylation products in comparison with Pichia henricii for assignment of configuration of products 2a and 11a after derivatisation with S-MPA. (C) 2016 Published by Elsevier Ltd.