一个试图氧化合的方法,以scholarinine A框架
Kerry E Jones1, Fernando Martínez Lara1, Blane P Zavesky2
1Department of Chemistry, University of California, Berkeley, CA 94720, United States.
Tetrahedron letters
|December 17, 2024
概括
研究人员探索了氧化碳-碳键的形成,用于化物合成. 一个受约束的基质导致了意想不到的碳键,突出了这些反应对特定分子结构的挑战.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 类化合物是一个重要的自然产品类别,具有多样化的药理活动.
- 氧化碳-碳键形成是构建复杂分子框架的关键策略,包括类化合物中发现的结构.
- 斯科拉林因A是一种类化合物的例子,其合成可以从高效的键形成方法学中获益.
研究的目的:
- 为了研究一种特定的氧化碳-碳键形成反应在构建化物支架上的实用性.
- 为了探索这种反应的应用,使用一种受结构约束的基质.
- 了解与将这种方法应用于复杂基质相关的局限性和挑战.
主要方法:
- 采用氧化反应,准道C3位置.
- 采用一种被限制的基板,该基板旨在与一个有酸组形成碳-碳键.
- 分析反应产物以识别形成的键并了解反应途径.
主要成果:
- 没有观察到醇C3和酸组之间所需的碳-碳键的形成.
- 在酸和醇C3位置之间形成了竞争的碳键.
- 该研究表明,基质的受约束性影响了反应结果.
结论:
- 探索的氧化反应并不普遍适用于所有基质,特别是那些受结构约束的基质.
- 碳键的形成突出显示了在特定的固体条件下可以占据主导地位的竞争途径.
- 这项工作扩大了对氧化碳-碳键形成的基质范围的理解,并确定了限制.
相关概念视频
Phase I Oxidative Reactions: Overview
233
Phase I biotransformation, or functionalization, is a crucial chemical process that converts drugs and other xenobiotics into more water-soluble forms, facilitating expulsion from the body. It involves oxidative, reductive, and hydrolytic reactions that add or unveil polar functional groups on lipophilic substrates. Key players in phase I reactions are the mixed-function oxidases. Situated in liver cell microsomes, these enzymes predominantly carry out drug metabolism. They require molecular...
233
Oxidation and Reduction of Organic Molecules
6.1K
Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...
The removal of an electron from a molecule, results in a...
6.1K
Redox Equilibria: Overview
522
A reduction-oxidation reaction is commonly called a redox reaction. In a redox reaction, electrons are transferred from one species to another rather than being shared between or among atoms. The reducing agent or reductant is the species that loses electrons and gets oxidized in the process. The species that gains electrons and gets reduced in the process is the oxidizing agent or oxidant. Redox reactions are represented as two separate equations called half-reactions, where one equation...
522
Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems
63
Oxidative reactions are pivotal in metabolizing numerous compounds, including pharmaceutical drugs. These reactions often occur in carbon-heteroatom systems, such as carbon-nitrogen, carbon-sulfur, and carbon-oxygen.
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
63
Oxidation of Phenols to Quinones
2.9K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
2.9K
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
142
Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
142


