methyl (S)-3-methyl-2-(3-oxobutylamido) n-butyric acid | 34990-55-1

• 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: methyl (S)-3-methyl-2-(3-oxobutylamido) n-butyric acid
• 英文别名: Methyl N-acetoacetyl-L-valinate；methyl (2S)-3-methyl-2-(3-oxobutanoylamino)butanoate
• CAS: 34990-55-1
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: KWICYEJIPNTQCK-VIFPVBQESA-N

物化性质

• 沸点：
  344.5±22.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-3-methyl-2-(3-oxobutylamido) n-butyric acid 在 lithium aluminium tetrahydride 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 乙腈 为溶剂， 生成 2-(4-Methoxy-phenyl)-5-methyl-3H-imidazole-4-carboxylic acid ((S)-1-hydroxymethyl-2-methyl-propyl)-amide
  参考文献：
  名称：

  Novel Synthetic Approach to 6,7-Dihydro-5H-imidazo[1,5-a]-pyrazin-8-ones

  摘要：

  [GRAPHICS]A novel route to highly substituted chiral 6,7-dihydro-5H-imidazo[1,5-a]pyrazine-8-ones starting from Meldrum's acid is disclosed. The key features of the methodology are the incorporation of amino esters as a chiral pool and facile mild intramolecular cyclization to form the pyrazine ring. Incorporation of various substituents at different stages of the synthesis from various building block sets makes this methodology readily amenable to parallel synthesis.

  DOI：

  10.1021/ol035455i
• 作为产物：
  描述：

  L-缬氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl (S)-3-methyl-2-(3-oxobutylamido) n-butyric acid
  参考文献：
  名称：

  真菌毒素tenuazonic acid的结构与植物毒性的关系

  摘要：

  摘要 Tenuazonic 酸（3-乙酰5-仲丁基吡咯烷-2,4-二酮）是由水稻Pyricularia oryzae 真菌病原体产生的代谢产物。它通过在核糖体水平干扰蛋白质合成来抑制植物的生长。我们已经合成了在 C-3 和 C-5 具有各种取代基的tenuazonic acid 类似物。除了仲丁基或正丙基之外的 C-5 上的取代基降低了类似物的植物毒性。但是 C-3 处的取代消除了毒性。因此，tenuazonic acid 似乎具有最佳的植物毒性结构。Tenuazonic acid 会诱导对米根霉具有抗性的活性品种的水稻叶片防御反应（褐变）。一些合成的类似物具有低水平的植物毒性，并且能够诱导活性水稻品种的叶片褐变。

  DOI：

  10.1016/0031-9422(88)80594-6

文献信息

• Fe(III) Complex Compounds For The Treatment And Prophylaxis Of Iron Deficiency Symptoms And Iron Deficiency Anemias
  申请人：Bark Thomas

  公开号：US20130109662A1

  公开（公告）日：2013-05-02

  The invention relates to iron(III) complex compounds and pharmaceutical compositions comprising them for the use as medicaments, in particular for the treatment and/or prophylaxis of iron deficiency symptoms and iron deficiency anemias.

  这项发明涉及铁（III）配合物和包括它们的药物组合物，用作药物，特别是用于治疗和/或预防缺铁症状和缺铁性贫血。
• One-Pot Two-Step Microwave-Assisted Synthesis of Alkylidene Acetoacetamido Esters, Useful Intermediates for β-Dehydropeptides
  作者：Angelo Viola、Lucia Ferrazzano、Roberto Greco、Lucia Cerisoli、Jonathan Caldi、Alessandra Tolomelli

  DOI：10.1002/ejoc.201600376

  日期：2016.7

  Alkylidene acetoacetamides are useful building blocks for the preparation of a number of biologically active derivatives, including dehydro-β-amino-acid-containing peptidomimetics. A one-pot two-step protocol for the preparation of amino-acid-derived unsaturated acetoacetamides has been optimized. The use of microwave activation avoids, or at least decreases, the need for catalysts in both steps. A

  亚烷基乙酰乙酰胺是制备许多生物活性衍生物的有用构件，包括含脱氢-β-氨基酸的肽模拟物。一种用于制备氨基酸衍生的不饱和乙酰乙酰胺的一锅两步方案已得到优化。微波活化的使用避免或至少减少了两个步骤中对催化剂的需要。从获得的小分子集合中选择亮氨酸衍生物以转化成相应的含脱氢-β-氨基酸的肽模拟物。已知这样的片段能够诱导β-转变成肽序列，并且由于不饱和的存在，它们可能代表选择性修饰和结合的位点。
• (R)-3-甲基-2-(3-氧代酰胺基)正丁酸酯
  申请人：烟台益诺依生物医药科技有限公司

  公开号：CN107857712B

  公开（公告）日：2022-09-09

  本发明提供一类（R）‑3‑甲基‑2‑（3‑氧代酰胺基）正丁酸酯化合物及其制备方法和药物用途，该类化合物能发挥保护脑缺血损伤的治疗作用，还可用于中枢神经系统创伤、情感障碍性疾病、癫痫、包括帕金森病、阿尔茨海默病、亨廷顿氏病等在内的神经退行性疾病等。
• Formation of Dihydropyridone- and Pyridone-Based Peptide Analogs through Aza-Annulation of β-Enamino Ester and Amide Substrates with α-Amido Acrylate Derivatives
  作者：Lars G. Beholz、Petr Benovsky、Donald L. Ward、Nancy S. Barta、John R. Stille

  DOI：10.1021/jo9600520

  日期：1997.2.1

  The aza-annulation of beta-enamino ester and amide substrates with the mixed anhydride of 2-acetamidoacrylic acid was used for the efficient construction of highly substituted alpha-acetamido delta-lactam products. With the alpha-acetamido substituent, lactam functionality, and gamma-carboxylate group, these delta-lactam products represent an interesting class of conformationally restricted dipeptide analogs. The framework of this lactam hub is structurally related to that of an alpha-amino acid coupled with a beta-amino acid. When alpha-amino esters derived from naturally occurring amino acids were used in the enamine formation step, subsequent aza-annulation led to branched peptide surrogates with two C-termini that extended from a common N-terminus. Oxidation of the aza-annulation products resulted in the generation of a planar system with peptide functionality radiating from the 1, 3, and 5 positions of the pyridone hub. Alternatively, pyridone products could be formed directly from the enamino amides by reaction with 2-phenyl-4-(ethoxymethylene)oxazolone. Subsequent hydrolysis of the acetamido and ester substituents of the N-benzylpyridones was selectively performed to access unique beta-amino acid products. Formation of the mixed anhydride of this acid, followed by amide bond formation with the ester of an alpha-amino acid, allowed extension of the peptide chain from the dihydropyridone structure.
• Sabri; El-Abadelah; Za'ater, Journal of the Chemical Society. Perkin transactions I, 1977, # 11, p. 1356 - 1359
  作者：Sabri、El-Abadelah、Za'ater

  DOI：——

  日期：——