催化甲基化的反应剂与PhSO2SeCH3
Xinyu Zhou1,2, Jiayi Liang1, Fengyin Duan1
1Affiliated Yueqing Hospital, Wenzhou Medical University, Wenzhou 325035, China.
Organic letters
|October 9, 2025
概括
一种新的甲基化试剂,PhSO2SeCH3,可以有效的电友甲基化利酸. 这种方法为抗瘤药物发现提供了功能化的阿里甲基化物.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 合成化学 合成化学
背景情况:
- 阿里甲基化物是开发新型抗瘤药物的关键中间体.
- 现有的合成阿里甲基化物的方法往往缺乏效率或可扩展性.
研究的目的:
- 设计和合成一种新的,稳定的,可扩展的甲基化试剂.
- 开发一种高效的方法,用于电友甲基化阿里酸试剂.
- 为了证明开发的方法在合成功能化的甲化的实用性,用于药物发现.
主要方法:
- 设计和制备硫甲基化物 (PhSO2SeCH3).
- 使用PhSO2SeCH3在 (CoCl2) 和1,10-phenanthroline (1,10-Phen) 的存在下,对酸的电友性甲基化.
- 该方法在晚期功能化和合成化化合物的应用.
主要成果:
- 一种稳定,易于处理和可扩展的甲基化试剂,PhSO2SeCH3,已成功制备.
- 一系列功能化的甲基化物从高效率的甲基试剂中合成.
- 该方法在生物活性分子的后期甲基化和三甲基化衍生物的合成中被证明是有效的.
结论:
- PhSO2SeCH3 是一种用于电友甲基化的一种强大而多用途的试剂.
- 开发的合成策略为获得甲基化物提供了一种有价值的工具,在抗瘤药物开发中具有潜在的应用.
- 该方法的可扩展性和适用于后期功能化的可用性突显了它在药物化学中的重要性.
相关概念视频
Preparation and Reactions of Sulfides
5.7K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.7K
Regioselectivity and Stereochemistry of Hydroboration
9.4K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.4K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
3.7K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.7K
Hydroboration-Oxidation of Alkenes
11.1K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
11.1K
Regioselectivity of Electrophilic Additions-Peroxide Effect
10.3K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.3K
α-Alkylation of Ketones via Enolate Ions
3.8K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.8K


![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)