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関連する概念動画

Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

15.1K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
15.1K
Halogenation of Alkenes02:46

Halogenation of Alkenes

21.2K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
21.2K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

4.4K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
4.4K
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

3.2K
A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
3.2K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

4.4K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
4.4K
Preparation of Epoxides03:00

Preparation of Epoxides

9.8K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
9.8K

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関連する実験動画

Updated: Apr 3, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.8K

ハロモン,プロカメノン,およびイソプロカメノンの高度選択的合成

Cyril Bucher1, Richard M Deans1, Noah Z Burns1

  • 1Department of Chemistry, Stanford University , Stanford, California 94305, United States.

Journal of the American Chemical Society
|September 24, 2015
PubMed
まとめ

ハロモンのような抗癌化合物を含めた 複雑なハロゲン化天然物質を 合成するための新しい方法を開発しました この画期的な発見により これらの貴重な分子の 選択的かつスケーラブルな生産が可能になりました

科学分野:

  • 有機化学
  • 自然製品合成
  • 薬剤化学

背景:

  • 160種類以上のキラル・ヴィチナル・ブロム塩化天然製品が知られている.
  • ハロゲン化有機分子の選択的合成は依然として課題です

研究 の 目的:

  • ハロゲンを選択的に組み込むための新しい合成方法を開発する.
  • イソプロカメノンとプロカメノンの最初の完全合成を 達成する.
  • ハロモンの抗がん剤の 拡張可能な合成を可能に

主な方法:

  • 新しく開発された化学,地域,およびエナチオ選択的二酸化反応を用いた.
  • イソプロカメノン,プロカメノン,ハロモンを合成した.

主要な成果:

  • イソプロカメノンとプロカメノンを 初めて合成した
  • ハロモンの選択的・スケーラブルな合成を達成した.
  • 複雑な天然製品に対する新しい二酸化反応の有用性を実証した.

結論:

  • 開発された二酸化酸化反応は,キラル近隣塩素化天然製品を合成するための強力なツールです.

さらに関連する動画

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.9K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K

関連する実験動画

Last Updated: Apr 3, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.8K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.9K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K
  • この研究は,抗がん作用を持つ重要な天然製品へのアクセスを提供します.
  • この方法論は,ハロゲン製薬の発見と開発のための新しい道を開きます.