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Facile Preparation of 4-Substituted Quinazoline Derivatives
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电化学驱动的迈克尔反应:基二乙烯的合成
Natalia V Moiseeva1, Alexey E Sokolov1, Igor V Trushkov1
1N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, Moscow 119991, Russian Federation. kokorekin@yandex.ru.
Organic & biomolecular chemistry
|December 18, 2024
概括
一种新的电压测量方法在温和条件下高效合成多种化二甲基. 这种电生成技术,随后添加醇,提供高产量,促进有机合成.
科学领域:
- 有机化学 有机化学
- 电化学 电化学 电化学
- 合成方法论 合成方法论
背景情况:
- 氨酸二甲基乙烯是有机合成中有价值的化合物.
- 现有的合成基二乙烯的方法可能需要恶劣的条件或缺乏多样性.
- 开发温和高效的合成路径对于获取这些化合物至关重要.
研究的目的:
- 开发一种原始的,温和的,高效的方法来合成多种多样的化二甲基.
- 为了利用电压计控制用于发电关键中间体.
- 为了在一系列基板上实现高产量.
主要方法:
- 电压计控制质子化p-金的电生成.
- 随后将各种 thiol 添加到发电中间体中.
- 反应条件的优化,以温和和高效.
主要成果:
- 成功合成了多种类型的化乙烯基乙烯的库.
- 取得的收益率在36%至99%之间.
- 证明了温和,电化学控制条件的有效性.
结论:
- 描述的电压计方法提供了一种通用且高效的途径,用于化二甲基.
- 这种方法在温和条件和广泛的基板范围方面具有优势.
- 发电策略是合成有机化学的一个有前途的工具.
相关概念视频
Preparation and Reactions of Thiols
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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Conjugate Addition of Enolates: Michael Addition
2.4K
The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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Preparation and Reactions of Sulfides
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Oxidation of Phenols to Quinones
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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...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Thermal Electrocyclic Reactions: Stereochemistry
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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