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関連する概念動画

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.4K
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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

8.0K
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.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

29.7K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
29.7K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.1K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.1K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.3K
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).
2.3K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.3K

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

7.4K

ダイオロマティブインドル (3 + 2) サイクル添加反応

Hui Li1, Russell P Hughes, Jimmy Wu

  • 1Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.

Journal of the American Chemical Society
|April 18, 2014
PubMed
まとめ
この要約は機械生成です。

新しいダイアステロ選択式無効反応により,機能化されたインドリン化合物の効率的な合成が可能になる. この方法は,天然製品のコア構造にアクセスし,反応機構を明らかにします.

さらに関連する動画

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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関連する実験動画

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 合成化学 合成化学とは
  • 薬用化学 薬用化学について

背景:

  • インドリン・スキャフォールは,重要な生物学的活動を持つ多くの天然製品に多く見られます.
  • 複雑な溶融インドリンへの効率的な合成経路の開発は,有機合成における重要な課題です.

研究 の 目的:

  • 機能化されたインドリン誘導体を合成するための新しいダイアステロセレクティブ (3 + 2) dearomative キャンセル反応を開発する.
  • 自然製品の簡潔な合成におけるこの方法の有用性を示すために.
  • 計算的研究を用いて反応機構を解明する.

主な方法:

  • 3-置換されたインドルをα-ハロケトンでダイアステロセレクティブ (3 + 2) dearomative キャンセルを開発しました.
  • 反応経路を調査するために,密度関数理論 (DFT) 計算 (B3LYP-D3/6-311++G**/MeOH) を利用した.
  • ビンコリン,イソコリミン,アスピドフィリンAのコア構造を合成する方法を適用した.

主要な成果:

  • キャンセル反応において,有意な地域化学的制御を達成した.
  • 高機能のサイクロペンタとサイクロヘキサと融合したインドリン化合物へのアクセスは容易でした.
  • DFTの研究は,2-ヒドロキシアリルカチオンとオキシアリルカチオン経路の両方の生存可能性を支持し,地域化学的および立体化学的結果を説明しました.

結論:

  • 開発された無効反応は,複雑なインドリンフレームワークを構築するための強力なツールです.
  • この方法論は,価値ある自然産物構造への簡潔な経路を提供します.
  • 計算分析は,運動および熱力学的好みを含む反応機構の詳細な理解を提供します.