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関連する概念動画

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.3K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.0K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.7K
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).
2.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.5K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
9.5K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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薬剤のようなビサイクロペンタンの銅媒介合成

Xiaheng Zhang1, Russell T Smith1, Chip Le1

  • 1Merck Center for Catalysis at Princeton University, Princeton, NJ, USA.

Nature
|February 18, 2020
PubMed
まとめ
この要約は機械生成です。

新しい1段階の多成分反応により,多様なビサイクロ[1.1.1]ペンタン (BCP) 化合物の迅速な合成が可能になる. このメタラフォトレドックス触媒プロトコルは 薬のような複雑な分子を作るための 時間効率の良い代替手段を提供します.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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関連する実験動画

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

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科学分野:

  • 合成有機化学
  • 薬剤化学
  • キャタリシス

背景:

  • 多成分反応は,化学合成のステップと原子の経済性において利点をもたらします.
  • Bicyclo[1.1.1]pentane (BCP) モチーフは,薬剤開発におけるベンゼンリングのバイオイソステルとしてますます使用されています.
  • [1.1.1]プロペランからポリ置換されたBCPを合成する現在の方法は,多くの場合,複数ステップで時間がかかります.

研究 の 目的:

  • 薬剤のような複雑なBCP製品の効率的な合成のための単段階の多成分反応を開発する.
  • BCP合成の伝統的な段階的なアプローチに対して,より時間効率の良い代替案を提供するためです.

主な方法:

  • [1.1.1]プロペランを含む1段階の3つの構成要素のラジカルカップリング反応.
  • メタルフォトレドックス触媒を用いて 銅を媒介したプロトコルです
  • 様々な原発前駆体とヘテロアトム核愛者を採用した.

主要な成果:

  • 一つのステップで様々な機能のバイサイクロペンタンを 合成しました
  • 反応には10種類以上の核愛素と様々な原始素 (アルキル,α-アシル,トリフローロメチル,スルフォニル) が含まれる.
  • 反応時間は5分から1時間でした
  • 有名な医薬品のBCP類型を生成し,そのうちの1つは代謝安定性を高めています.

結論:

  • 開発されたメタルフォトレドックスプロトコルは,複雑なBCP構造への迅速かつ効率的な経路を提供します.
  • この方法は,医学化学の応用のための貴重なBCPモチーフの合成を大幅に効率化します.
  • このプロトコルの汎用性とスピードは 薬の発見と開発のための強力なツールです