関連する実験動画
Updated: Jan 19, 2026
02:29
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
12.7K
阻害されたダイアルキルエーテル合成と電気生成カルボケーション
Jinbao Xiang1,2, Ming Shang1, Yu Kawamata1
1Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Nature
|September 11, 2019
まとめ
阻害されたエーテルを合成するには,炭酸から炭酸塩を生成する電気化学を用いてより簡単です. この方法では,価値ある阻害されたエーテルと関連化合物を効率的に生成し,以前の合成の課題を克服します.
科学分野:
- 有機化学
- 合成化学
- 電気化学
背景:
- 阻害されたエーターは,その代謝の安定性のために,薬剤化学で価値があります.
- 阻害されたエーサーの従来の合成は困難で,アクセシビリティを制限しています.
- 阻害されたエーサーの未開拓の化学空間は,合成のボトルネックを提示します.
研究 の 目的:
- 阻害されたエーテルを合成するためのシンプルで効率的な経路を開発する.
- 有機合成における電気化学的に生成されたカルボケーションの有用性を探求する.
- エーテルモチーフへのアクセスのための伝統的な方法の限界を克服する.
主な方法:
- 炭酸酸の電気化学的酸化により,炭酸塩酸が生成される.
- 非酸性条件下でアルコールのドナーとカルボケーションの反応.
- カーボケーションとヌクレオフィルを挟んで,阻害アルコールとアルキルフッ化物を形成する.
主要な成果:
- 阻害されたエーテル合成のための新しい電気化学的方法が確立されました.
- 80種類以上の様々な阻害エーテルが製造され,広範な適用性を示した.
- この方法は12の化学構造の 合成ボトルネックを解決し,収穫量を増やし,ステップを減らしました
- 阻害アルコールとアルキルフッ素も,カルボケーション中間物質を用いて合成された.
結論:
- 電気化学は,穏やかな条件下で非常に反応性の高い中間物質にアクセスするための強力なツールを提供します.
- この方法は,貴重な阻害エーテルおよび関連する化合物を合成する効率を大幅に改善します.
- 開発された反応マニホールドは,以前の合成の制限を克服し,以前はアクセスできない化学構造にアクセスできます.
関連する概念動画
02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
12.7K
Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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02:10Carbocations
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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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02:28Structure and Nomenclature of Ethers
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Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
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02:36Crown Ethers
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Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules...
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02:17Physical Properties of Ethers
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Overview
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
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02:23Autoxidation of Ethers to Peroxides and Hydroperoxides
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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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