(S)-3-(N-methylamino)butanoic acid

• 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: (S)-3-(N-methylamino)butanoic acid
• 英文别名: (S)-N-methyl-3-aminobutyric acid；S-N-methyl-3-aminobutyric acid；N-methyl-3-aminobutyric acid；(3S)-3-(methylazaniumyl)butanoate
• 化学式: C₅H₁₁NO₂
• mdl: MFCD12131685
• 分子量: 117.148
• InChiKey: VWQSQYOPIHNGBY-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-3-Cbz-氨基丁酸 在 palladium on activated charcoal 4 A molecular sieve 、 camphor-10-sulfonic acid 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (S)-3-(N-methylamino)butanoic acid
  参考文献：
  名称：

  Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones

  摘要：

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.

  DOI：

  10.1021/jo0700326

文献信息

• Evaluating β-amino acids as enantioselective organocatalysts of the Hajos–Parrish–Eder–Sauer–Wiechert reaction
  作者：Stephen G. Davies、Angela J. Russell、Ruth L. Sheppard、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b711171a

  日期：——

  A systematic study of the effect of substitution within the β-amino acid framework indicates that both β2- and β3-amino acids catalyse the Hajos–Parrish–Eder–Sauer–Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained β-amino acid (1R,2S)-cispentacin, which catalyses the Hajos–Parrish–Eder–Sauer–Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

  对β-氨基酸框架内取代效应的系统研究表明，β2-和β3-氨基酸催化Hajos–Parrish–Eder–Sauer–Wiechert反应的对映选择性较低至合理。这些结果促使对构象受限的β-氨基酸(1R,2S)-cispentacin进行评估，该氨基酸催化Hajos–Parrish–Eder–Sauer–Wiechert反应的对映选择性与L-脯氨酸相比相当或更高。
• Cyclombandakamines A₁and A₂, Oxygen-Bridged Naphthylisoquinoline Dimers from a Congolese<i>Ancistrocladus</i>Liana
  作者：Blaise Kimbadi Lombe、Torsten Bruhn、Doris Feineis、Virima Mudogo、Reto Brun、Gerhard Bringmann

  DOI：10.1021/acs.orglett.7b00209

  日期：2017.3.17

  Cyclombandakamines A1 (1) and A2 (2), both with an unprecedented pyrane–cyclohexenone–dihydrofuran sequence and six stereocenters and two chiral axes, are the first oxygen-bridged dimeric naphthylisoquinoline alkaloids. They were isolated from the leaves of an as yet unidentified Congolese Ancistrocladus species. Their stereostructures were established by spectroscopic, chemical, and chiroptical methods

  Cyclombandakamines A 1（1）和A 2（2）都是氧桥联的二聚萘基异喹啉生物碱，它们具有前所未有的吡喃-环己烯酮-二氢呋喃序列，并具有六个立体中心和两个手性轴。它们是从尚未鉴定的刚果Ancistrocladus物种的叶子中分离出来的。它们的立体结构是通过光谱，化学和按摩方法结合DFT和TDDFT计算而建立的。它们显然源自“开链”萘基异喹啉二聚体的一系列氧化环化反应，并表现出显着的抗原生动物活性。
• Gentrymine B, an N -Quaternary Ancistrocladus Alkaloid: Stereoanalysis, Synthesis, and Biomimetic Formation from Gentrymine A 1
  作者：Gerhard Bringmann、Michael Ochse、Manuela Michel

  DOI：10.1016/s0040-4020(99)01054-6

  日期：2000.1

  The total synthesis of the N-quaternary isoquinoline alkaloid gentrymine B (1) and of its unnatural enantiomer as well as its oxidative degradation is described. A further proof of stereostructure and hints at the biosynthetic origin of the unusual S,S-configuration in gentrymine B (1) were obtained by an additional biomimetic synthesis of 1 from the related-but 1R-configured-natural product gentrymine A (2), by N-methylation and subsequent spontaneous epimerization at C-l. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones
  作者：Brad E. Sleebs、Andrew B. Hughes

  DOI：10.1021/jo0700326

  日期：2007.4.1

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.