一种不同的单硫-迈克尔策略,以创建β-二烯合的二林
Jagmeet Singh1, Abhijeet Singh1, Mahendra Nath1
1Department of Chemistry, Faculty of Science, University of Delhi, Delhi 110 007, India. mnath@chemistry.du.ac.in.
Organic & biomolecular chemistry
|May 13, 2024
概括
一个新的一多米诺策略高效地合成了 (II) 和铜 (II) 的β-thiophene-fused tetraarylporphyrins. 这种方法利用醇-迈克尔添加用于具有改变光物理性质的新型氨酸衍生物.
科学领域:
- * 有机化学 有机化学
- * 材料科学 材料科学
- * 超分子化学 超分子化学
背景情况:
- * 氨酸是重要的宏环化合物,具有多样化的应用.
- * 开发高效的功能氨酸合成路径至关重要.
- *与烯融合的氨酸具有独特的电子和光学特性.
研究的目的:
- * 开发一种新的单多米诺策略,用于合成β-二烯合的二烯.
- * 探索 (II),铜 (II) 和自由基氨酸衍生物的合成.
- * 调查新合成的化合物的光物理性质.
主要方法:
- * 一多米诺反应,涉及提-迈克尔添加.
- *从2-formylporphyrins和初级氨基酸中合成2-iminoporphyrinsin situ.
- *使用金属酸盐用于金属烯酸形成的金属插入.
主要成果:
- *成功合成了 (II) 和铜 (II) 的β-thiophene融合的5,10,15,20-tetraarylporphyrins.
- *形成了一种新型的自由基[2,3-b]-meso-tetrakis ((4-甲基) 氨酸.
- *新合成的氨酸与原始四氨酸氨酸相比,具有适度的低染色移位电子吸收.
结论:
- * 开发的单多米诺策略对于合成β-thiophene-fused porphyrins是有效的.
- * 合成协议允许制备各种金属烯衍生物.
- *新型氨酸具有独特的光物理特性,对潜在的应用有价值.
相关概念视频
Preparation and Reactions of Sulfides
4.8K
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.
4.8K
Preparation and Reactions of Thiols
6.2K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.2K
Conjugate Addition of Enolates: Michael Addition
2.5K
The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
2.5K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
5.9K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
5.9K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.2K
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).
2.2K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
3.0K
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...
3.0K


![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)