氧化氨基化环裂变的Catechols为粘液酸单尼特里尔
Jianwei Yan1, Yiwan Jiang1, Xiaobing Li1
1School of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, P. R. China.
Organic letters
|September 25, 2025
概括
研究人员开发了一种有效的氧化环开放反应,产生cis,cis-酸单. 这种可扩展的方法为替代的甲基醇提供了高选择性,在有机合成中证明了其实用性.
科学领域:
- 有机化学 有机化学
- 合成方法论 合成方法论
- 反应工程的反应工程.
背景情况:
- 甲基醇衍生物是有机合成中的重要组成部分.
- 有效的方法功能化catechols对于访问复杂的分子至关重要.
- 氧化环开放反应为有价值的化学中间体提供了独特的途径.
研究的目的:
- 为了建立一个高效的氧化环开放反应的catechols.
- 在温和的条件下合成cis,cis-酸单尼.
- 调查开发的转换的基质范围和可扩展性.
主要方法:
- 甲基醇的氧化环开放.
- 温和的反应条件.
- 广泛的基质范围评估.
- 格拉姆级反应的优化.
- 使用实验数据和DFT计算的机制研究.
主要成果:
- 开发了一种高效的方法来从catechols中合成cis,cis-muconic酸 mononitriles.
- 反应在温和条件下进行,具有广泛的基质范围.
- 不对称地替换的甲基醇主要产生一种单一的产物.
- 反应是可扩展到克的数量.
- 提出了一种反应机制,涉及到pyrocatechol氧化,金胺凝结,核友添加和环裂变.
结论:
- 已经实现了一种实用且高效的氧化环开放反应,用于catechol功能化.
- 开发的方法可以选择性地获取cis,cis-酸单.
- 反应的可扩展性和温和条件突出显示了其对工业应用的潜力.
相关概念视频
Alkynes to Carboxylic Acids: Oxidative Cleavage
6.7K
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
6.7K
Acid-Catalyzed Ring-Opening of Epoxides
8.7K
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...
8.7K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.8K
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).
2.8K
Base-Catalyzed Ring-Opening of Epoxides
10.0K
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...
10.0K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
3.7K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
3.7K
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
5.3K
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
5.3K


