(2R,1'R)-2-(1-hydroxy-1-phenylmethyl)pentanenitrile | 264229-59-6

• 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)pentanenitrile
• 英文别名: (2R)-2-[(R)-hydroxy(phenyl)methyl]pentanenitrile
• CAS: 264229-59-6
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: CMJFIJJHWGTYFM-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 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：

  (2R,1'R)-2-(1-hydroxy-1-phenylmethyl)pentanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (5R,6R)-6-phenyl-5-propyl-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：

  苯戊醇 在 盐酸 、 三(五氟苯基)硼烷 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 水 、 甲苯 为溶剂， 反应 11.0h， 生成 (2R,1'R)-2-(1-hydroxy-1-phenylmethyl)pentanenitrile
  参考文献：
  名称：

  磺酰氰对烯烃的立体特异性氧氰化

  摘要：

  在三（五氟苯基）硼烷（B（C 6 F 5）3 ）作为催化剂存在下，使用对甲苯磺酰氰（TsCN）进行烯烃的分子间氧氰化被证明是可行的。开发的方法提供了一种简单、可扩展且直接的方法来获取合成有用的β-羟基腈衍生物。

  DOI：

  10.1002/anie.202218743

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.
• An Efficient Diastereoselective Reduction of α-Alkyl-β-keto Carbonitriles with TiCl4/BH3 or LiBH4/CeCl3 to syn- or anti-α-Alkyl-β-hydroxy Carbonitriles
  作者：Renato Dalpozzo、Giuseppe Bartoli、Marcella Bosco、Antonio De Nino、Antonio Procopio、Letizia Sambri、Antonio Tagarelli

  DOI：10.1002/1099-0690(200108)2001:15<2971::aid-ejoc2971>3.0.co;2-k

  日期：2001.8

  alpha -Alkyl-beta -keto carbonitriles can be reduced stereoselectively to syn- and anti-alpha -alkyl-beta -hydroxy carbonitriles. The stereoselectivity can be explained in terms of properties of the Lewis acid employed. TiCl4 in noncoordinating solvents such as dichloromethane, followed by reduction with the borane/pyridine complex, predominantly led to the syrz-alpha -alkyl-beta -hydroxy carbonitriles, according to a chelate transition state, whereas CeCl3 in coordinating solvents such as THF, followed by reduction with LiBH4, predominantly led to the anti-isomers, in agreement with an open-chain transition state. The reduction to syn-alpha -alkyl-beta -hydroxy carbonitriles is the first general preparation of these compounds.