(1R,2R)-2-(aminomethyl)-1-phenylpentan-1-ol | 366814-93-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-2-(aminomethyl)-1-phenylpentan-1-ol
• CAS: 366814-93-9
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: DRDLHGNHLLIVRP-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 (1R,2R)-2-(aminomethyl)-1-phenylpentan-1-ol 以 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：

  (2R,1'R)-2-(1-hydroxy-1-phenylmethyl)pentanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (1R,2R)-2-(aminomethyl)-1-phenylpentan-1-ol
  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

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。
• Stereoselective Complete Reduction of α-Alkyl-β-ketonitriles toanti γ-Amino Alcohols
  作者：Antonio De Nino、Renato Dalpozzo、Giovanna Cupone、Loredana Maiuolo、Antonio Procopio、Antonio Tagarelli、Giuseppe Bartoli

  DOI：10.1002/1099-0690(200209)2002:17<2924::aid-ejoc2924>3.0.co;2-5

  日期：2002.9

  The one-pot reduction of alpha-alkyl-beta-ketonitriles to anti gamma-amino alcohols can be efficiently performed by borane/dimethyl sulfide complex in the presence of cerium chloride as Lewis acid. Selectivities are slightly worse than monoreduction but this drawback is overcome by much better yields. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
• 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.