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関連する概念動画

Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

2.7K
Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
2.7K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.3K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.9K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
18.9K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.1K
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

4.5K
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
4.5K
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

9.1K
Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.       
9.1K

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関連する実験動画

Updated: Sep 14, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

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異なるアルキルアミンの挿入によるα,β-不飽和ケトンのスキップ

Huiguang Yu1,2, Lili Xu1,2, Luyao Li1,2

  • 1Department of Gastrointestinal Oncology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430072, China.

Journal of the American Chemical Society
|July 22, 2025
PubMed
まとめ

この研究は,α,β-不飽和ケトンのための新しい骨格編集戦略を導入し,炭素-炭素結合に選択的なアミンの挿入を可能にします. この方法は 医薬品や天然製品を含む複雑な分子を 合成するための強力な新しい経路を提供します

さらに関連する動画

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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関連する実験動画

Last Updated: Sep 14, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.1K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.3K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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科学分野:

  • 有機化学
  • 合成方法論
  • 薬剤化学

背景:

  • α,β-不飽和カルボニル化合物は重要な合成中間物質である.
  • 主要なアミンは 薬の発見と生物活性分子合成に不可欠です
  • これらの化合物にアミンを挿入する既存の方法は限られている.

研究 の 目的:

  • α,β-不飽和ケトンの異なる骨格編集戦略を開発する.
  • 選択的な2,3および3,4アミンをC−C結合に挿入する.
  • 伝統的な方法に対する地域選択的で補完的な代替手段を提供すること.

主な方法:

  • アミン挿入のための反応剤制御プロトコルを使用します.
  • 地域選択性アジリジンの中間形を用いる.
  • 骨格編集のための標的型C-C結合割れを実行します.

主要な成果:

  • α,β-不飽和ケトンにアルキルアミンを選択的に組み込むことが実証されています.
  • 調整可能な挿入部位は,制御されたアジリジン形成とC-C結合分裂によって達成される.
  • アミン挿入製品の単発合成を可能にした.

結論:

  • 開発された戦略は,α,β-不飽和ケトンの骨格編集のための新しいアプローチを提供します.
  • この方法は,シュミット反応と比較して異なる地域選択性を提供します.
  • 薬の発見と天然製品の合成に価値のある様々なピリジル同位体の合成を容易にする.