(2R,1'R)-2-(1-Hydroxy-1-phenylmethyl)butanenitrile | 264229-57-4

• 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)butanenitrile
• 英文别名: (2R)-2-[(R)-hydroxy(phenyl)methyl]butanenitrile
• CAS: 264229-57-4
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: KCNXDVXKPJLPBY-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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)butanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (5R,6R)-5-ethyl-6-phenyl-1,3-oxazinan-2-one
  参考文献：
  名称：

  Biotransformations of benzoylacetonitrile with the fungus Curvularia lunata: highly diastereo- and enantioselective synthesis of α-alkyl β-hydroxy nitriles and γ-amino alcohols

  摘要：

  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。

  DOI：

  10.1039/a909721j
• 作为产物：
  描述：

  2-乙基-3-氧代-3-苯基丙腈 在 甲酸 、 C₃₈H₄₀ClN₂O₃RhS 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以97%的产率得到(2R,1'R)-2-(1-Hydroxy-1-phenylmethyl)butanenitrile
  参考文献：
  名称：

  动态动力学拆分法对α-取代-β-酮腈进行不对称加氢

  摘要：

  描述了用于α-取代的-β-酮腈的对映体和非对映体选择性还原的催化方案。该反应涉及DKR-ATH方法，该方法同时构建具有两个连续的立体异构中心的β-羟基甲腈支架。以高产率（94％–98％）和出色的对映和非对映选择性（高达> 99％ee，高达> 99：1 dr）获得了多种α-取代-β-酮腈。非对映选择性的起源也通过DFT计算得到了合理化。此外，这种方法可以快速获得异戊ox酮和他喷他多的药物中间体。

  DOI：

  10.1021/jacs.0c13273

文献信息

• Preparation of enantiomerically enriched aromatic β-hydroxynitriles and halohydrins by ketone reduction with recombinant ketoreductase KRED1-Pglu
  作者：Martina L. Contente、Immacolata Serra、Francesco Molinari、Raffaella Gandolfi、Andrea Pinto、Diego Romano

  DOI：10.1016/j.tet.2016.05.027

  日期：2016.7

  A NADPH-dependent benzil reductase (KRED1-Pglu) was used as recombinant enzyme for catalysing the reduction of different functionalised ketones. The reactions were carried out in the presence of a catalytic amount of NADP+ and an enzyme-coupled transformation (oxidation of glucose catalysed by glucose dehydrogenase), for regenerating the cofactor and thus driving the reaction to completion. KRED1-Pglu

  NADPH依赖的苯甲酰还原酶（KRED1-Pglu）被用作重组酶，用于催化不同功能化酮的还原。反应在催化量的NADP +存在下进行酶偶联转化（葡萄糖脱氢酶催化的葡萄糖氧化），用于再生辅因子，从而驱动反应完成。KRED1-Pglu具有出色的通用性，能够在不同的pH值下还原不同的β-酮腈和α-卤代酮。值得注意的是，根据底物的性质，KRED1-Pglu可用于高效，清洁的酶促还原反应，避免了由于培养基pH引起的副反应。还原通常以高对映选择性发生，从而可以高产率制备对映体富集的β-羟基腈和卤代醇。在所有情况下，减少的立体化学结果均遵循所谓的Prelog规则。
• 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。
• 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.
• 8-Amino-5,6,7,8-tetrahydroquinolines as ligands in iridium(III) catalysts for the reduction of aryl ketones by asymmetric transfer hydrogenation (ATH)
  作者：Daniele Zerla、Giorgio Facchetti、Marco Fusè、Michela Pellizzoni、Carlo Castellano、Edoardo Cesarotti、Raffaella Gandolfi、Isabella Rimoldi

  DOI：10.1016/j.tetasy.2014.06.003

  日期：2014.7

  Aqua iridium(III) complexes with 8-amino-5,6,7,8-tetrahydroquinolines CAMPY L1 and its derivatives as chiral ligands proved to be very efficient catalysts for the reduction of a wide range of prochiral aryl ketones, revealing a variety of behaviours in terms of reaction rate and stereoselectivity. As standard substrates, differently substituted acetophenones were studied and good enantioselectivity (86% ee) was achieved in the reduction of 1-(o-tolyl)ethan-1-one 6. Particularly interesting was the ATH reaction in the case of beta-amino keto esters, precursors of beta-lactams and azetidinones. The best results were obtained with [Cp*Ir(H2O)(L1)]SO4 affording the corresponding diastereomeric alcohols in an (R,S)-configuration with an excellent 99% ee in the reduction of 2-(benzamido methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl) propanoate 12. (C) 2014 Elsevier Ltd. All rights reserved.
• Asymmetric Transfer Hydrogenation of α-Substituted-β-Keto Carbonitriles via Dynamic Kinetic Resolution
  作者：Fangyuan Wang、Tilong Yang、Ting Wu、Long-Sheng Zheng、Congcong Yin、Yongjie Shi、Xiang-Yu Ye、Gen-Qiang Chen、Xumu Zhang

  DOI：10.1021/jacs.0c13273

  日期：2021.2.17

  A catalytic protocol for the enantio- and diastereoselective reduction of α-substituted-β-keto carbonitriles is described. The reaction involves a DKR-ATH process with the simultaneous construction of β-hydroxy carbonitrile scaffolds with two contiguous stereogenic centers. A wide range of α-substituted-β-keto carbonitriles were obtained in high yields (94%–98%) and excellent enantio- and diastereoselectivities

  描述了用于α-取代的-β-酮腈的对映体和非对映体选择性还原的催化方案。该反应涉及DKR-ATH方法，该方法同时构建具有两个连续的立体异构中心的β-羟基甲腈支架。以高产率（94％–98％）和出色的对映和非对映选择性（高达> 99％ee，高达> 99：1 dr）获得了多种α-取代-β-酮腈。非对映选择性的起源也通过DFT计算得到了合理化。此外，这种方法可以快速获得异戊ox酮和他喷他多的药物中间体。