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関連する概念動画

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Oxidation of Alcohols02:37

Oxidation of Alcohols

In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems01:19

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems

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...

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関連する実験動画

Updated: Jul 22, 2026

Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications
09:22

Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications

Published on: August 28, 2015

炭化水素酸化によるマクロラクトニゼーション.

Kenneth J Fraunhoffer1, Prabagaran Narayanasamy, Lauren E Sirois

  • 1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.

Journal of the American Chemical Society
|July 13, 2006
PubMed
まとめ

新しいパラジアム触媒反応により,オメガアルケノ酸のマクロラクトニゼーションが可能になる. この効率的な方法は,複雑な分子合成に有用な,幅広い基板範囲と高い機能群耐性を実証しています.

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • カタリシス カタリシス カタリシス
  • 合成方法論 合成方法論

背景:

  • マクロラクトニゼーションは,複雑な天然製品や医薬品を合成する際の重要な変化です.
  • 既存の方法は,しばしば厳しい条件を必要とし,幅広い機能グループとの互換性が欠けている.

研究 の 目的:

  • 新しく,効率的で,広く適用可能な,パラジウム触媒によるマクロラクトニゼーション反応の開発.
  • 様々なラクトンを合成するための反応機構と範囲を調査する.

主な方法:

  • 線形オメガアルケノ酸のマクロラクトニゼーションのために,新しいPd/硫酸化物触媒システムを利用しました.
  • シリアルリガンド触媒によるアリルC-H酸化経路を使用した.
  • 様々なアリル,アルキル,不飽和酸の反応範囲を調査し,機能群の適合性を評価した.

主要な成果:

  • オメガアルケノ酸の効率的なマクロラクトニゼーションが,新しいPd/硫酸化物触媒システムによって達成された.
  • (Z) -アルファ,ベータ不飽和酸を含む,同位体化のない広範な基板範囲が実証されています.
  • ペプチドやエステルなどの生物学的に重要な部分と高機能群の互換性を示した.

さらに関連する動画

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-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

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
11:42

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

関連する実験動画

Last Updated: Jul 22, 2026

Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications
09:22

Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications

Published on: August 28, 2015

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-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

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
11:42

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

結論:

  • 報告されたPd/硫酸化物触媒反応は,マクロラクトン合成のための強力な新しいツールを提供します.
  • 反応は,テンプレートされたpi-allylPdカルボキシラート中間体からの内球機能化を経由して進行する.
  • この方法論は,複雑な分子合成の効率,範囲,および機能群の許容性という点で重要な利点を提供します.