(S)-2-azido-3-methylpentan-1-ol | 848828-70-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-2-azido-3-methylpentan-1-ol
• 英文别名: (2S)-2-azido-4-methylpentan-1-ol
• CAS: 848828-70-6
• 化学式: C₆H₁₃N₃O
• 分子量: 143.189
• InChiKey: WOYMUTATNIHZHI-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-azido-3-methylpentan-1-ol 在 三氟甲磺酸 、 sodium hydride 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (S)-1-benzyl-4-(1'-(benzyloxy)-3'-methylpentan-2'-yl)-1,4-diazepan-5-one
  参考文献：
  名称：

  Modular Synthesis of Cyclic Peptidomimetics Inspired by γ-Turns

  摘要：

  A series of peptidomimetics based on a gamma-turn motif were synthesized using a modular approach, in which N-protected piperidones were reacted with a selection of 2-hydroxyalkyl azides derived from common L-amino acids. Hydrolysis of the initially formed iminium ethers afforded the targeted series of substituted 1,4-diazepin-5-ones.

  DOI：

  10.1021/ol047323a
• 作为产物：
  描述：

  L-亮氨醇 在 4-二甲氨基吡啶 、 triflic azide 、 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以59%的产率得到(S)-2-azido-3-methylpentan-1-ol
  参考文献：
  名称：

  Universal Peptidomimetics

  摘要：

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.

  DOI：

  10.1021/ja1071916

文献信息

• Nucleophilic Addition to Iminium Ethers in the Preparation of Functionalized <i>N</i>-Alkyl Heterocycles
  作者：Erik Fenster、Brenton T. Smith、Vijaya Gracias、Gregory L. Milligan、Jeffrey Aubé

  DOI：10.1021/jo702193g

  日期：2008.1.1

  synthesized by the reactions of ketones with hydroxyalkyl azides. These cationic species react with a variety of nucleophiles via two possible pathways. The initially formed, kinetic product arises from direct addition to the iminium carbon in the substrate. In some cases, the initial adduct reverts to the starting iminium ether and the ultimate product arises from nucleophilic displacement at the

  双环亚胺醚可以通过酮与羟烷基叠氮化物的反应来合成。这些阳离子物质通过两种可能的途径与多种亲核试剂反应。最初形成的动力学产物来自直接添加到基材中的亚胺碳中。在某些情况下，最初的加合物还原为起始的亚胺醚，最终产物来自O-烷基上的亲核取代，以提供末端官能化的N取代的酰胺。通过使用几种亚胺醚研究了一系列亲核试剂的行为。通常，可以通过表征所形成的产物来鉴定相关途径。对于氢氧化物的添加，无论机理如何，其只能提供一种产物，使用18 O标记的氢氧化物通过动力学途径显示了反应的发生。还开发了一种功能化内酰胺的一锅合成方法，该方法首先用羟烷基叠氮化物处理酮，然后进行亲核加成处理。
• Novel Application of α-Azido Aldehydes in Multicomponent Reactions: Synthesis of Triazolo-Fused Dihydrooxazinones via a Passerini Reaction–Dipolar Cycloaddition Strategy
  作者：Fabio De Moliner、Stefano Crosignani、Andrea Galatini、Renata Riva、Andrea Basso

  DOI：10.1021/co200072z

  日期：2011.9.12

  α-Azido aldehydes can be employed in Passerini reactions with isocyanides and various propiolic acids to afford the three-component adducts in moderate to good yields. These compounds undergo a straightforward azide-alkyne dipolar cycloaddition to furnish triazolo-fused dihydrooxazinones.

  α-叠氮基醛可与异氰化物和各种丙酸一起用于Passerini反应中，以中等至良好的收率得到三组分加合物。这些化合物经过直接的叠氮化物-炔烃偶极环加成反应，得到三唑并稠合的二氢恶嗪酮。
• Synthesis of 5-Carboxamide-oxazolines with a Passerini−Zhu/Staudinger−Aza−Wittig Two-Step Protocol
  作者：Fabio De Moliner、Stefano Crosignani、Luca Banfi、Renata Riva、Andrea Basso

  DOI：10.1021/cc100122n

  日期：2010.9.13
• Universal Peptidomimetics
  作者：Eunhwa Ko、Jing Liu、Lisa M. Perez、Genliang Lu、Amber Schaefer、Kevin Burgess

  DOI：10.1021/ja1071916

  日期：2011.1.26

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.
• Modular Synthesis of Cyclic Peptidomimetics Inspired by γ-Turns
  作者：Senthil Kumar Ramanathan、John Keeler、Huey-Lih Lee、D. Srinavasa Reddy、Gerald Lushington、Jeffrey Aubé

  DOI：10.1021/ol047323a

  日期：2005.3.1

  A series of peptidomimetics based on a gamma-turn motif were synthesized using a modular approach, in which N-protected piperidones were reacted with a selection of 2-hydroxyalkyl azides derived from common L-amino acids. Hydrolysis of the initially formed iminium ethers afforded the targeted series of substituted 1,4-diazepin-5-ones.