(S)-(+)-Carnitinamid-Hydrochlorid | 5261-99-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(+)-Carnitinamid-Hydrochlorid
• 英文别名: (S)-(+)-carnitinamide chloride；(S)-carnitine amide chloride；(S)-carnitinamide chloride；D-Carnitinamid-chlorid；D-carnitinamide chloride；(+)-Carnitinamidchlorid；[(2S)-4-amino-2-hydroxy-4-oxobutyl]-trimethylazanium;chloride
• CAS: 5261-99-4；6490-19-3；6490-20-6；67942-00-1
• 化学式: C₇H₁₇N₂O₂*Cl
• 分子量: 196.677
• InChiKey: MVOVUKIZAZCBRK-RGMNGODLSA-N

物化性质

• 熔点：
  213-214℃
• 密度：
  1.296[at 20℃]
• LogP：
  -4 at 20℃

计算性质

• 辛醇/水分配系数(LogP)：
  -4.07
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  (S)-(+)-Carnitinamid-Hydrochlorid 在 盐酸 、 Amberlite IRA-402 、 水 、 碳酸氢钠 作用下， 反应 73.0h， 生成 左旋肉碱
  参考文献：
  名称：

  Bernabei, Ida; Castagnani, Roberto; Angelis, Francesco De, Chemistry - A European Journal, 1996, vol. 2, # 7, p. 826 - 831

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-氰基-2-羟基丙基)三甲基氯化铵 在 盐酸 、 silver(l) oxide 作用下， 反应 504.0h， 生成 (S)-(+)-Carnitinamid-Hydrochlorid
  参考文献：
  名称：

  乙酰肉碱和其他肉碱衍生物异构体的合成

  摘要：

  肉碱，γ-三甲基铵-β-羟基丁酸，由γ-氯-β-羟基丁腈合成。乙酰肉碱是通过乙酰肉碱的酯化或肉碱的乙酰化制备的。

  DOI：

  10.1139/v69-192

文献信息

• Enantiomeric resolution of a carnitinamide salt by preferential crystallization
  申请人：UNIVERSITA' DEGLI STUDI DI MILANO

  公开号：EP1852416A1

  公开（公告）日：2007-11-07

  A process for the resolution of (D,L)-carnitinamide (D,L-I) chloride in its enantiomers (D-I) and (L-I), characterized in that a supersaturated solution or suspension of (D,L-I) in a suitable solvent or mixture of solvents, optionally added with a surfactant, is used. A series of alternate preferential crystallizations is carried out after adding minimum amount of seeds of one of the two enantiomers, (D-I) or (L-I), that is to be precipitated, and subsequently restoring the supersaturation conditions by adding an appropriate amount of (D,L-I) racemate.

  一种解决(D,L)-肉碱酰胺(D,L-I)氯化物的对映体(D-I)和(L-I)的过程，其特征在于使用适当溶剂或溶剂混合物中(D,L-I)超饱和溶液或悬浮液，可选地加入表面活性剂。在加入少量(D-I)或(L-I)中的一种对映体晶种后，进行一系列交替的优先结晶，并通过加入适量的(D,L-I)外消旋体恢复超饱和条件。
• From carnitinamide to 5-aminomethyl-2-oxazolidinones
  作者：Cristiano Bolchi、Marco Pallavicini、Matteo Binda、Laura Fumagalli、Ermanno Valoti

  DOI：10.1016/j.tetasy.2012.02.006

  日期：2012.2

  Carnitinamide chloride, an immediate synthetic precursor of carnitine, was chlorinated at the amide nitrogen. The resultant carnitinechloramide chloride, when treated with a base, revealed that the first-formed isolable and characterisable carnitinechloramide inner salt undergoes solid state conversion into 5-trimethylammoniomethyl-2-oxazolidinone chloride via Hoffmann rearrangement and intramolecular cyclization of the beta-hydroxyisocyanate. The trimethylaminomethyl substituent at C-5 of the 2-oxazolidinone was converted into a dimethylaminomethyl group by microwave-assisted demethylation in DMF and then into a methylaminomethyl group by decomposition of the alpha-chloroethyl carbamate obtained by treatment with alpha-chloroethyl chloroformate. This sequence of reactions was then applied to both (S)- and (R)-carnitinamide chloride without any racemization to yield both enantiomers of 5-aminomethyl-2-oxazolidinones that are mono-, di- and tri-methylated at the exocyclic nitrogen. (C) 2012 Elsevier Ltd. All rights reserved.
• Bernabei, Ida; Castagnani, Roberto; Angelis, Francesco De, Angewandte Chemie, 1994, vol. 106, # 20, p. 2202 - 2203
  作者：Bernabei, Ida、Castagnani, Roberto、Angelis, Francesco De、Witt Scalfaro, Paolo De、Giannessi, Fabio、et al.

  DOI：——

  日期：——
• Entrainment resolution of carnitinamide chloride
  作者：Marco Pallavicini、Cristiano Bolchi、Matteo Binda、Rossana Ferrara、Laura Fumagalli、Oreste Piccolo、Ermanno Valoti

  DOI：10.1016/j.tetasy.2008.06.011

  日期：2008.7

  The ready availability of(R)-carnitinamide, an immediate synthetic precursor of (R)-carnitine, is an ambitious goal and resolutions, due to the very low cost of racemic carnitinamide, can be the most convenient stereotechnology to reach it. We have efficiently resolved carnitinamide chloride by preferential crystallization from methanol according to simple entrainment procedure. The previous transformation of the chloride into other salts or the use of specific solvent systems was not required for successful resolution, as in the case of the reported entrainment of carnitinamide precursor, carnitine nitrile. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of isomers of acetylcarnitylcholine and other carnitine derivatives
  作者：Gabor Kato、E. A. Hosein

  DOI：10.1139/v69-192

  日期：1969.4.1

  Carnitine, γ-trimethylammonium-β-hydroxy butyric acid, was synthesized from γ-chloro-β-hydroxy butyronitrile. Acetylcarnitylcholine was prepared either by the esterification of acetylcarnitine or by the acetylation of carnitylcholine.

  肉碱，γ-三甲基铵-β-羟基丁酸，由γ-氯-β-羟基丁腈合成。乙酰肉碱是通过乙酰肉碱的酯化或肉碱的乙酰化制备的。