(R)-4-氰基-3-羟基丁酰胺 | 244094-04-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (R)-4-氰基-3-羟基丁酰胺
• 英文名称: (R)-4-cyano-3-hydroxybutyramide
• 英文别名: (3R)-4-Cyano-3-hydroxybutanamide
• CAS: 244094-04-0
• 化学式: C₅H₈N₂O₂
• 分子量: 128.131
• InChiKey: JGNICYPMHKZAGS-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为产物：
  描述：

  R(-)-4-氰基-3-羟基丁酸乙酯 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (R)-4-氰基-3-羟基丁酰胺
  参考文献：
  名称：

  4-cyano-3-hydroxybutanoyl hydrazines, derivatives and process for the

  摘要：

  本文介绍了4-氰基-3-羟基丁酰肼（10），特别是R-手性中间体。这些中间体在制备（R）-3-羟基-4-三甲基氨基丁酸（L-肉碱）和R-4-氨基-3-羟基丁酸（GABOB）以及医学上有用的手性化学中间体方面非常有用。

  公开号：

  US06114566A1

文献信息

• Process for the preparation of R-(-)-carnitine
  申请人：——

  公开号：US20010031892A1

  公开（公告）日：2001-10-18

  R-(−)-carnitine is prepared by (a) conversion of (S)-3-hydroxy-4-butyrolactone [1] to alkyl (S)-4-halogen-3-hydroxy-butyrate [2] by reaction with a linear or branched C 1 -C 7 alcohol (b), substitution of a CN group for the halogen of compound [2] to yield the alkyl ester of (R)-4-cyano-3-hydroxybutyric acid [3], (c) conversion of alkyl ester [3] to yield (R)-4-cyano-3-hydroxybutyramide [4], (d) cyclization of compound [4] to yield (R)-5-(cyanomethyl)-2-oxazolidone [5] via conversion of the amide function to isocyanate, (e) hydrolysis of compound [5] to yield (R)-4-amino-3-hydroxybutyric acid [6], and finally (f) methylation of the amino group of compound [6] to yield the end product (R)-carnitine.

  (R)-(−)-肉碱的制备方法：(a)将(S)-3-羟基-4-丁酸内酯[1]与一种直链或支链的C1-C7醇[b]反应，得到烷基(S)-4-卤代-3-羟基丁酸酯[2]，(b)将化合物[2]的卤素替换为CN基，得到(R)-4-氰基-3-羟基丁酸酯[3]，(c)将烷基酯[3]转化为(R)-4-氰基-3-羟基丁酰胺[4]，(d)通过将酰胺功能团转化为异氰酸酯，使化合物[4]环化，得到(R)-5-(氰甲基)-2-噁唑烷酮[5]，(e)水解化合物[5]，得到(R)-4-氨基-3-羟基丁酸[6]，最后(f)将化合物[6]的氨基甲基化，得到最终产物(R)-肉碱。
• 4-cyano-3-hydroxybutanoyl hydrazines, derivatives and process for the
  申请人：Board of Trustees Operating Michigan State University

  公开号：US06114566A1

  公开（公告）日：2000-09-05

  Novel 4-cyano-3-hydroxybutanoyl hydrazides (10), particularly R-chiral intermediates are described. The intermediates are useful in preparing (R)-3-hydroxy-4-trimethylaminobutyric acid (L-carnitine) and R-4-amino-3-hydroxybutyric acid (GABOB) and chiral chemical intermediates which are medically useful.

  本文介绍了4-氰基-3-羟基丁酰肼（10），特别是R-手性中间体。这些中间体在制备（R）-3-羟基-4-三甲基氨基丁酸（L-肉碱）和R-4-氨基-3-羟基丁酸（GABOB）以及医学上有用的手性化学中间体方面非常有用。
• 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.