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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
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.
2.8K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.9K
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.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
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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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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  3. サイクロペンタノンの炭素結合の触媒活性化
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  3. サイクロペンタノンの炭素結合の触媒活性化

関連する実験動画

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

10.9K

サイクロペンタノンの炭素結合の触媒活性化

Ying Xia1,2, Gang Lu3, Peng Liu3

  • 1Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, USA.

Nature
|November 5, 2016

PubMed で要約を見る

まとめ
この要約は機械生成です。

研究者らは,サイクルケトンの無圧性炭素-炭素結合を活性化するための新しい触媒方法を開発しました. この突破により 機能化されたテトラロンや天然製品を含む 複雑な分子の効率的な合成が可能になりました

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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関連する実験動画

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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科学分野:

  • 有機化学
  • カタリシス
  • 合成方法論

背景:

  • 炭素の骨格は 化学産業のほとんどの分子に 基礎をなしています
  • 炭素と炭素の単一結合 (C−C結合) を活性化することは,複雑な有機分子合成に不可欠である.
  • 既存の方法は多くの場合,ストレートリングシステムに依存し,広範な適用性を制限しています.

研究 の 目的:

  • シンプルなサイクルケトンにおける不張力C−C結合の活性化のための一般的触媒的アプローチを開発する.
  • 多様な分子構造と 複雑な有機構造の合成を可能にします
  • 機能化されたα-テトラロンと天然製品の合成の効率を向上させる.

主な方法:

  • ロジウム前触媒をN-ヘテロサイクルカルベンのリガンドとアミノピリジン共触媒と組み合わせて使用した.
  • 単純なサイクロペンタノンとサイクロヘクサノン,特にC3位置にアリル基を持つものにこの方法を適用した.
  • 反応メカニズムを解明するために,密度関数理論の計算を使用した.

主要な成果:

  • サイクロペンタノンとサイクロヘクサノンのC-C結合の触媒活性化が達成された.
  • 有機合成における重要な構造モチーフである機能化されたα-テトラロンの効率的な合成が実証された.
  • テルペノイド天然産物のエナチオセレクティブ合成の効率が向上した.
  • 計算分析でロジウムブリッジのバイサイクルの中間物質を特定した.

    • 結論:

    • 開発された方法は,非ストレインサイクルケトンの触媒C−C結合活性化に対する一般的で効率的なアプローチを提供します.
    • この方法論は複雑な有機分子や 自然製品を作るためのツールキットを拡張します
    • この発見は,有機化学と医薬品化学における合成経路の簡素化のための新しい可能性を提供します.