(-)-(R)-4-amino-2-methylbutanoic acid | 96192-37-9

• 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)-4-amino-2-methylbutanoic acid
• 英文别名: (R)-2MeGABA；(2R)-4-azaniumyl-2-methylbutanoate
• CAS: 96192-37-9
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: AEBRINKRALSWNY-SCSAIBSYSA-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：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(R)-4-amino-2-methylbutanoic acid 在 四氢呋喃 、 lithium aluminium tetrahydride 作用下， 生成 (R)-4-氨基-2-甲基丁醇
  参考文献：
  名称：

  The Absolute Configuration of the C₈-Atom in the Pyrrolizidine Moieties of the Senecio Alkaloids

  摘要：

  DOI：

  10.1021/ja01530a063
• 作为产物：
  描述：

  惕各酸乙酯 在 palladium on activated charcoal 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 氢气 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 20.0~140.0 ℃ 、405.3 kPa 条件下， 反应 182.0h， 生成 (-)-(R)-4-amino-2-methylbutanoic acid
  参考文献：
  名称：

  Synthesis and resolution of 2-methyl analogues of GABA

  摘要：

  E-4-Amino-2-methylbut-2-enoic acid, (+/-)-4-amino-2-methylbutanoic acid, (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid, which are analogues of the inhibitory neurotransmitter GABA (gamma-aminobutyric acid, 4-aminobutanoic acid), were synthesised from ethyl 2-methyl-4-phthalimidobut-2-enoate, ethyl 2-methyl-4-phthilimidobutanoate, (+)+2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2S)-methyl-4-phthalimidobutanoate and (-)-[(2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2R)-methyl-4-phthalimidobutanoate, respectively. The assignment of the absolute configuration of (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid was based on the X-ray crystallographic structure of the (+)-(R,S)-diastereoisomer, and direct comparison of specific rotations with the published data for (-)-(R)-4-amino-2-methylbutanoic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.002

文献信息

• Total Synthesis and Antitrypanosomal Activity of Janadolide and Simplified Analogues
  作者：Jonathan H. Chung、Arthur H. Tang、Kieran Geraghty、Leo Corcilius、Marcel Kaiser、Richard J. Payne

  DOI：10.1021/acs.orglett.0c00840

  日期：2020.4.17

  Herein, we describe the total synthesis of janadolide, along with eight simplified analogues, via an efficient solid-phase strategy. Crucial to the synthesis of the natural product was the construction of a key polyketide fragment via an enantioselective (−)-B-chlorodiisopinocampheylborane-mediated reduction and a B-alkyl Suzuki reaction. Janadolide and the simplified analogues exhibited antitrypanosomal

  Janadolide是从海洋蓝藻Okeania sp分离出的一种环状二肽天然产物。在这里，我们通过有效的固相策略描述了janadolide的总合成以及八个简化的类似物。天然产物的合成至关重要的是通过对映选择性（-）- B-氯二异opinocampheylborane介导的还原反应和B-烷基铃木反应来构建关键的聚酮化合物片段。Janadolide和简化的类似物对病原性布氏锥虫罗得氏菌和克氏锥虫具有抗锥虫活性。
• Enantioselective synthesis of 2-substituted 4-aminobutanoic acid (GABA) analogues via cyanomethylation of chiral enolates
  作者：Shamim Azam、Alice A. D'Souza、Peter B. Wyatt

  DOI：10.1039/p19960000621

  日期：——

  Cyanomethylation by bromoacetonitrile of sodium or lithium enolates derived from (4S,5R)-3-acyl-4-methyl-5-phenyl-1,3-oxazolidin-2-ones usually shows good stereoselectivity; although the reaction of 3-(3-carboxypropanoyl)oxazolidinone 5d is exceptionally unselective, the 3-(pent-4-enoyl)- and 3-(3,4-dimethoxyhydrocinnamoyl)oxazolidinones 5e and 5f are found to be effective synthetic equivalents of 5d. The cyanomethylation products can be converted into 2-substituted derivatives of 4-aminobutanoic acid (γ-aminobutyric acid, GABA) by the alkaline hydrolysis of the oxazolidinone chiral auxiliary followed by hydrogenation of the cyano group.

  由溴乙腈对源自(4S,5R)-3-酰基-4-甲基-5-苯基-1,3-恶唑烷-2-酮的钠或锂烯醇盐进行的氰甲基化通常显示出良好的立体选择性；尽管3-(3-羧基丙酰)恶唑烷酮5d的反应特别不选择性，3-(戊-4-烯酰)和3-(3,4-二甲氧基氢桂皮酰)恶唑烷酮5e和5f被发现是5d的有效合成等价物。这些氰甲基化产物可以通过恶唑烷酮手性辅助剂的碱性水解，并随之对氰基进行氢化，转化为4-氨基丁酸（γ-氨基丁酸，GABA）的2-取代衍生物。
• Asymmetric Synthesis of α-Alkyl-ω-amino Acids and α-Alkyllactams
  作者：Antje Rottmann、M. Bartoczek、Jürgen Liebscher

  DOI：10.1055/s-1997-4465

  日期：1997.3

  A versatile access to optically active α-branched ω-amino acids 8 and 9 and corresponding lactams 11 was developed allowing the synthesis of either enantiomer of these products. This asymmetric synthesis is based on amino alcohols 3 as chiral auxiliaries, which were converted to 2-(ω-benzenesulfonylaminoalkyl)oxazolines 4 by reaction with ω-amino-imido esters 2 or derivatives of lactams 1. The 2-(ω-benzenesulfonylaminoalkyl)oxazolines 4 were deprotonated by LDA and α-alkylated by alkyl halides 5. Final hydrolytic cleavage of the oxazoline ring afforded the amino acids 8 and 9 or lactams 11. The method does not follow Meyers model of α-alkylation of 2-alkyloxazolines and requires BEt3 as additive in order to achieve complete stereoselectivity.

  我们开发了一种通用的方法，用于光学活性β-支链-氨基酸8和9以及相应的内酰胺11，从而能够合成这些产品的对映体。这种不对称合成基于氨基醇3作为手性助剂，通过与β-氨基-亚胺酯2或内酰胺1的衍生物反应转化为2-(β-苯磺酰氨基烷基)恶唑啉4。2-(β-苯磺酰氨基烷基)恶唑啉4通过LDA脱质子化，并通过烷基卤化物5进行β-烷基化。最终通过水解裂解恶唑啉环得到氨基酸8和9或内酰胺11。该方法不遵循2-烷基恶唑啉的β-烷基化Meyers模型，需要添加BEt3以实现完全的立体选择性。
• The preparation of enantiomerically enriched γ-amino acids (GABAs) using palladium catalysed allylic substitution
  作者：Christopher J. Martin、David J. Rawson、Jonathan M.J. Williams

  DOI：10.1016/s0957-4166(98)00383-8

  日期：1998.10

  Enantioselective palladium catalysed allylic substitution reactions have been employed as the asymmetry-producing step in the synthesis of enantiomerically enriched gamma-amino acids. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 10.24820/ark.5550190.p011.106dummy2
  作者：González-Alvarez, Carmen María、Mendoza, Angel、Ortiz, Aurelio、Sabala, Rocio、Sansinenea, Estibaliz

  DOI：10.24820/ark.5550190.p011.106dummy2

  日期：——