硫二--5-甲基四基烯酸的合成
Meng-Yang Chang1,2,3, Kuan-Ting Chen1
1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University Kaohsiung 807 Taiwan mychang@kmu.edu.tw.
RSC advances
|October 16, 2023
概括
这项研究提出了使用DABCO催化剂的硫四基的高产量,单合成. 该方法通过立体选择式取消过程有效地创建关键的碳-氧和碳-碳键.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 迈克尔的加法反应是有机合成的基础.
- 四基衍生物是天然产品和药品中重要的结构动图.
研究的目的:
- 开发一种新的,高产的,单合成途径,用于硫二--5-甲基四.
- 通过双重迈克尔添加-化序列实现立体选择性取消.
主要方法:
- 使用1,4-diazabicyclo[2.2.2]octane (DABCO) 作为一种催化剂.
- 采用一个单反应,涉及β-硫尼尔烯和2-甲基-1-propenol.
- 利用贝利斯-希尔曼型反应机制.
主要成果:
- 成功合成了具有高产量的硫二--5-甲基四基.
- 一个立体选择式取消过程的演示.
- 在单个过程中形成一个碳-氧和一个碳-碳键.
结论:
- 开发的方法提供了一种高效和简单的方法来合成有价值的硫四基架.
- 由DABCO促进的并列反应为立体选择性C-O和C-C键形成提供了一个强大的工具.
相关概念视频
Preparation and Reactions of Sulfides
4.9K
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.
4.9K
Five-Membered Heterocyclic Aromatic Compounds: Overview
4.0K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.0K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Aromatic Hydrocarbon Cations: Structural Overview
2.8K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
Removing one hydrogen from the intervening CH2 group...
2.8K
Preparation of Nitriles
2.1K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.1K

![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)
