Jove
Visualize
お問い合わせ
JoVE
x logofacebook logolinkedin logoyoutube logo
JoVEについて
概要リーダーシップブログJoVEヘルプセンター
著者向け
出版プロセス編集委員会範囲と方針査読よくある質問投稿
図書館員向け
推薦の声購読アクセスリソース図書館諮問委員会よくある質問
研究
JoVE JournalMethods CollectionsJoVE Encyclopedia of Experimentsアーカイブ
教育
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab Manual教員リソースセンター教員サイト
利用規約
プライバシーポリシー
ポリシー

関連する概念動画

Preparation of Epoxides03:00

Preparation of Epoxides

9.2K
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...
9.2K
Sharpless Epoxidation02:57

Sharpless Epoxidation

5.1K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
5.1K
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

7.9K
Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
7.9K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

8.8K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
8.8K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.1K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.1K
Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

21.6K
A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
21.6K

こちらも読む

関連記事

共著者、ジャーナル、引用グラフによってこの研究に関連する記事。

並び替え
Same author

Dual-component water-lean diamines as high-efficiency CO<sub>2</sub> absorbents: unveiling the two-fold role of proton acceptors.

Chemical communications (Cambridge, England)·2026
Same author

Ultrastrong Polyketone Hot-Melt Adhesives Enabled by Ni-Catalyzed Carbonylative Polymerization.

Journal of the American Chemical Society·2026
Same author

Systematic Catalyst Variation for Improved Stereoselective Epoxide Polymerization: Subtle Modifications Resulting in Superior Efficiency.

Journal of the American Chemical Society·2026
Same author

Intramolecularly Synergic Catalysis Enables Efficient Closed-Loop Recycling of Polyesters and Polycarbonates.

Angewandte Chemie (International ed. in English)·2026
Same author

π-π Interaction Promoting Kinetic Resolution Copolymerization of <i>rac</i>-Epoxides and Isocyanates.

Journal of the American Chemical Society·2026
Same author

Living Carbonylative Polymerization of Vinylarenes Using P-Chirogentic Pd Catalyst: A Route to Functionalized Polyketone with Chirality Recognition.

Angewandte Chemie (International ed. in English)·2025

関連する実験動画

Updated: Jan 25, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
13:05

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Published on: June 28, 2019

8.7K

レイセミックエポキシドとアンヒドリドのエナンチオセレクティブ解像度共聚化:ステレオレギュラーポリエステルとキラルエポキシドのための効率的なアプローチ

Jie Li1, Bai-Hao Ren1, Zhao-Qian Wan1

  • 1State Key Laboratory of Fine Chemicals , Dalian University of Technology , Dalian 116024 , China.

Journal of the American Chemical Society
|May 14, 2019
PubMed
まとめ

この研究では,エナチオセレクティブ共ポリメリゼーションを用いた異質性ポリエステルとキラルエポキシドの製造のための新しい方法が導入されています. このプロセスは高いエナチオ選択性を達成し,調節可能な融点を持つ半結晶ポリマーを生産します.

さらに関連する動画

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

7.8K
A Micropatterning Assay for Measuring Cell Chirality
08:07

A Micropatterning Assay for Measuring Cell Chirality

Published on: March 11, 2022

2.7K

関連する実験動画

Last Updated: Jan 25, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
13:05

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Published on: June 28, 2019

8.7K
Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

7.8K
A Micropatterning Assay for Measuring Cell Chirality
08:07

A Micropatterning Assay for Measuring Cell Chirality

Published on: March 11, 2022

2.7K

科学分野:

  • ポリマー化学
  • 非対称な触媒
  • 有機合成

背景:

  • アイソタクティックポリマーとキラルエポキシドの制御された合成は,依然として重要な課題です.
  • エナンチオセレクティブの運動解像度は,エナンチオピュア化合物を得るために極めて重要です.

研究 の 目的:

  • エナチオセレクティブ解離共ポリメリゼーションのための効率的な戦略を開発する.
  • 高いイソタキシ性ポリエステルと 価値のあるキラルエポキシドを製造する.
  • キラル誘導における触媒構造の役割を調査する.

主な方法:

  • ラセミク末端エポキシドとアンヒドリドのエナンチオセレクティブ運動解像度共聚化.
  • キラルリガンドと核愛性コカタリストを併用した 純二金属複合体を利用する.
  • ポリマーの微細構造,戦術性,熱的性質の特徴

主要な成果:

  • 様々なラセミックエポキシドに対して,例外的なエナチオセレクティブ性 (運動解像度係数 > 300) を達成した.
  • 選択性因子300以上で完全に交替する構造を持つ高同位性共ポリマーです.
  • 合成された半結晶型ポリエステルで,融解温度77~160°C,ポリ分散度が低い.

結論:

  • 開発された触媒システムは,イソタキシ性ポリエステルとキラルエポキシドの効率的な製造を可能にします.
  • リガンドのキラリティは,運動解像度共聚化において高いエナチオ選択性を達成する鍵となる.
  • この方法は,制御されたステレオ化学で,明確に定義された半結晶ポリマーへの堅固な経路を提供します.