(R)-4-amino-3-hydroxybutyronitrile | 121799-47-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-4-amino-3-hydroxybutyronitrile
• 英文别名: (3R)-4-amino-3-hydroxybutanenitrile
• CAS: 121799-47-1
• 化学式: C₄H₈N₂O
• 分子量: 100.12
• InChiKey: AFSJSMGLWQBMPX-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-amino-3-hydroxybutyronitrile 在 盐酸 作用下， 反应 6.0h， 以80%的产率得到(R)-(-)-4-氨基-3-羟基丁酸
  参考文献：
  名称：

  Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB

  摘要：

  Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified ceramic particles (PS-C) in diisopropyl ether gave the best results. The use of base additives in this transesterification drastically reduces the reaction time without effecting the yields or enantioselectivities. Resolved 3-hydroxy-4-trityloxybutanenitrile has been utilized for the synthesis of enantiomerically pure 5-tosyloxymethyl-1,3-oxazolidine-2-one, which is an important intermediate for the preparation of beta-adrenergic blocking agents and oxazolidinone based antimicrobial agents. Enantiomerically pure (R)-3-hydroxy-4-trityloxybutanenitrile and (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one have been utilized in the enantioconvergent synthesis of (R)-GABOB. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.04.019
• 作为产物：
  描述：

  (R)-3-hydroxy-4-(p-toluenesulfonyloxy)butyronitrile 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 以80%的产率得到(R)-4-amino-3-hydroxybutyronitrile
  参考文献：
  名称：

  Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB

  摘要：

  Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified ceramic particles (PS-C) in diisopropyl ether gave the best results. The use of base additives in this transesterification drastically reduces the reaction time without effecting the yields or enantioselectivities. Resolved 3-hydroxy-4-trityloxybutanenitrile has been utilized for the synthesis of enantiomerically pure 5-tosyloxymethyl-1,3-oxazolidine-2-one, which is an important intermediate for the preparation of beta-adrenergic blocking agents and oxazolidinone based antimicrobial agents. Enantiomerically pure (R)-3-hydroxy-4-trityloxybutanenitrile and (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one have been utilized in the enantioconvergent synthesis of (R)-GABOB. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.04.019

文献信息

• Immobilized benzylpenicillin acylase: Application to the synthesis of optically active forms of carnitin and propranalol
  作者：Claudio Fuganti、Piero Grasselli、P.Fausto Seneci、Stefano Servi、Paolo Casati

  DOI：10.1016/s0040-4039(00)84449-4

  日期：1986.1

  the presence of immobilized benzylpenicillin acylase of the N-phenacetyl derivatives of the primary amines (3)-(5) affords the hydroxy amines (6)-(8), key intermediates in the synthesis of optically active forms of carnitin and propranalol, of ca. 0.4, 0.3 and 0.8 ee, respectively.

  在伯胺（3）-（5）的N-苯乙酰基衍生物固定化苄青霉素酰基转移酶存在下于pH 7.5水解可提供羟胺（6）-（8），这是旋光形式合成中的关键中间体肉碱和普萘洛尔，约。分别为0.4、0.3和0.8 ee。
• Synthetic routes to l-carnitine and l-gamma-amino-beta-hydroxybutyric acid from (S)-3-hydroxybutyrolactone by functional group priority switching
  作者：Guijun Wang、Rawle I. Hollingsworth

  DOI：10.1016/s0957-4166(99)00169-x

  日期：1999.5

  (R)-3-Hydroxy-4-trimethylaminobutyric acid (L-carnitine) and (R)-4-amino-3-hydroxybutyric acid (GABOB) are two compounds with a very high level of medical significance. They can be prepared from (R)-3-hydroxy-gamma-butyrolactone which is not readily available in significant quantities. The corresponding (S)-lactone is available in large quantities but attempts at inverting the stereochemistry of the hydroxyl group lead to elimination to give the furanone. Here we describe a straightforward route to these two compounds, starting from (S)-3-hydroxy-gamma-butyrolactone by adding a highly oxidized carbon at one end whilst removing one carbon from the other, thus switching the functional group priorities. In this method, the lactone is transformed to an (R)-4-cyano-3-hydroxybutyric acid ester which is then converted to an acyl hydrazide by treatment with hydrazine. This stable, crystalline hydrazide has not been described before. It is readily converted to (R)-4-amino-3-hydroxybutyronitrile, a precursor of L-carnitine and GABOB, by Curtius rearrangement under conditions that do not result in deamination. (C) 1999 Elsevier Science Ltd. All rights reserved.