methyl (S)-2-bromo-4-methyl-pentanoate | 114438-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (S)-2-bromo-4-methyl-pentanoate
• 英文别名: (S)-Methyl2-bromo-4-methylpentanoate；methyl (2S)-2-bromo-4-methylpentanoate
• CAS: 114438-66-3
• 化学式: C₇H₁₃BrO₂
• 分子量: 209.083
• InChiKey: SRPGFJDOALJGMR-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-bromo-4-methyl-pentanoate 在 palladium on activated charcoal 盐酸 、 sodium azide 、 hemin copolymer 2 、 氢气 作用下， 反应 18.5h， 生成 L-leucine isopropyl ester
  参考文献：
  名称：

  使用含血红素的新型聚合物负载试剂进行烷基卤的亲核取代反应

  摘要：

  通过悬浮共聚反应合成了一种由氯化血红素、二乙烯基苯和2-甲基-5-乙烯基吡啶组成的新型高分子试剂。伯、仲和叔烷基卤与氯化血红素共聚物与氰化物、叠氮化物和硫氰酸根离子的取代反应得到了令人满意的产率。根据立体化学研究，该反应机理被揭示为 SNi 型。氯化血红素共聚物不仅是具有功能性的聚合物负载试剂，而且还用于将产物与反应混合物分离。

  DOI：

  10.1246/bcsj.62.2562
• 作为产物：
  描述：

  L-亮氨酸 在 硫酸 、 sodium bromide 、 sodium nitrite 作用下， 以 硫酸 为溶剂， 反应 8.0h， 生成 methyl (S)-2-bromo-4-methyl-pentanoate
  参考文献：
  名称：

  用于合成 β2-氨基酸的新型可扩展不对称氨基甲基化反应

  摘要：

  β-氨基酸是设计拟肽的有用工具，开发其合成的新方法，尤其是 β2-氨基酸的合成，仍然是一个重要的挑战。在这里，我们报告了一种新的可扩展路线，该路线基于 Mannich 型亚胺鎓亲电试剂对甲硅烷基乙烯酮 N,O-缩醛的氨甲基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600926

文献信息

• Efficient Synthesis of β²-Amino Acid by Homologation of α-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile
  作者：Roba Moumne、Solange Lavielle、Philippe Karoyan

  DOI：10.1021/jo060316a

  日期：2006.4.1

  Development of new methods for the synthesis of β-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of β2-amino acids by homologation of α-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.

  合成β-氨基酸的新方法的开发是重要的，因为这些化合物的聚合物是药物化学中有希望的拟肽候选物。我们在这里报告我们发现一个新的，高效的总体战略为合成β 2 -氨基酸的α氨基酸的亿安科技，涉及reformatsky反应和曼尼希型亚铵电体。
• Synthesis, Characterization, Docking Studies and Antiepileptic Activity of Novel Piracetam Derivatives
  作者：Nidhi Dhama、Sucheta、Aadesh Kumar、Vikrant Verma、Rohan Narkhede、Vaishali M. Patil

  DOI：10.14233/ajchem.2023.24037

  日期：——

  Piracetam is a nootropic drug that has been used in clinical trials for decades, but is still a mystery due to a lack of understanding of its mechanism of action. In this research, sixteen novel piracetam derivatives were synthesized in three steps and characterized by IR, NMR and mass spectroscopic techniques. Based on the docking studies, two derivatives were identified as more active based on the drug receptor interactions studies and were further subjected to animal studies for the evaluation of the activity. Compounds 6 and 10 had shown a strong anticonvulsant activity based on the molecular docking studies. It was hypothesized from the synthesized analogues that the non-substitution with thio moiety at has a major effect on reducing the contagiousness of seizure discharge and increasing the seizure threshold.

  吡拉西坦（Piracetam）是一种已在临床试验中使用了数十年的促智药物，但由于对其作用机制缺乏了解，至今仍是一个谜。 但由于对其作用机制缺乏了解，至今仍是一个谜。在这项研究中，通过三个步骤合成了十六种新型吡拉西坦衍生物 并通过红外光谱、核磁共振和质谱技术对其进行了表征。 在对接研究的基础上，通过对药物受体 相互作用研究，确定了两种活性更强的衍生物，并进一步进行了动物实验以评估其活性。 根据分子对接研究，化合物 6 和 10 显示出很强的抗惊厥活性。 的抗惊厥活性。根据合成的类似物推测，不取代硫代基 在降低癫痫放电的传染性和提高癫痫发作阈值方面具有重要作用。 阈值。
• An optimized BRD4 inhibitor effectively eliminates NF-κB-driven triple-negative breast cancer cells
  作者：Guan-Jun Yang、Ying-Qi Song、Wanhe Wang、Quan-Bin Han、Dik-Lung Ma、Chung-Hang Leung

  DOI：10.1016/j.bioorg.2021.105158

  日期：2021.9
• A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics
  作者：Vommina V. Sureshbabu、B. Vasantha、G. Nagendra

  DOI：10.1016/j.tetlet.2011.12.093

  日期：2012.3

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Characterization of Chiral N−O Turns Induced by α-Aminoxy Acids
  作者：Dan Yang、Bing Li、Fei-Fu Ng、Yi-Long Yan、Jin Qu、Yun-Dong Wu

  DOI：10.1021/jo010376a

  日期：2001.11.1

  Chiral alpha -aminoxy acids of various side chains were synthesized with high optical purity starting from chiral alpha -amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.