(R)-3-methyl-4-aminobutyric acid | 1116-92-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-3-methyl-4-aminobutyric acid
• 英文别名: R-(-)-4-Amino-3-methyl-buttersaeure；(3R)-4-azaniumyl-3-methylbutanoate
• CAS: 1116-92-3
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: CZGLBWZXGIAIBU-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-3-methylglutaramide 在 bis-(trifluoroacetoxy)-iodo-benzene 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以84%的产率得到(R)-3-methyl-4-aminobutyric acid
  参考文献：
  名称：

  Andruszkiewicz, Ryszard; Barret, Anthony G. M.; Silverman, Richard B., Synthetic Communications, 1990, vol. 20, # 1, p. 159 - 166

  摘要：

  DOI：

文献信息

• The 5-exo-trig radical cyclization reaction under reductive and oxidative conditions in the synthesis of optically pure GABA derivatives
  作者：Verónica Rodríguez、Mario Sánchez、Leticia Quintero、Fernando Sartillo-Piscil

  DOI：10.1016/j.tet.2004.09.053

  日期：2004.11

  Free radical precursors 4a and 4b were synthesized and treated under reductive or oxidative conditions to obtain the corresponding optically pure pyrrolidinones 5-8, which were subsequently transformed into corresponding optically pure GABA derivatives 9-11. When reductive radical conditions (4a-->7 and 8) were used, a Ph1-5 migration product 14 was obtained; presumably depending upon the specific conformation of the rotamer precursor and also 14 was found to be a kinetic product. (C) 2004 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of γ-aminobutyric acid derivatives by Ni(II)-catalyzed reaction of diethyl malonate with nitroalkenes
  作者：A. N. Reznikov、E. V. Golovin、Yu. N. Klimochkin

  DOI：10.1134/s1070428013050047

  日期：2013.5

  A new synthetic approach to (3R)-4-amino-3-methylbutyric acid and [(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetamide [(R)-phenotropil] has been developed. Asymmetric center with a required configuration has been generated via enantioselective addition of diethyl malonate to 1-nitropropene and beta-nitrostyrene, catalyzed by Ni(II) complexes with (R,R)- and (S,S)-N,N'-dibenzylcyclohexane-1,2-diamine.