基因的连续流合成来自isoxazolones
Aisling Loftus1, Rosa De Gregorio1, Marcus Baumann1
1University College Dublin, School of Chemistry, Science Centre South, D04 N2E5 Dublin, Ireland. marcus.baumann@ucd.ie.
一种新的连续流程方法可以有效地从isoxazolones中产生alkynes. 这种方法克服了批量限制,为这个关键功能组提供了快速合成,提高了安全性和可扩展性.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 过程化学 过程化学
背景情况:
- 类的合成在有机化学中至关重要.
- 传统的批量方法用于从异醇中产生基因,受到变量产量,安全性问题和可扩展性问题的限制.
- 外热反应和有毒气体释放使批处理复杂化.
研究的目的:
- 开发一种连续流的方法,用于从异类中合成类.
- 为了克服与传统批量方法相关的局限性.
- 提供一种更安全,更可扩展和更有效的基因合成方法.
主要方法:
- 使用了连续流反应堆设置.
- 采用了二氧化的条件,用于异佐的转化.
- 优化了反应参数,以快速生成基.
主要成果:
- 在不到1分钟的居住时间内实现了高效的基因生成.
- 证明的生产率大约为每小时2克.
- 成功生产了各种基因产品.
- 克服了变量产量的问题,过度使用试剂,以及批处理固有的安全问题.
结论:
- 连续流的方法为基合成提供了相对于批量方法的显著改进.
- 这种方法通过控制外热反应和最大限度地减少有毒气体释放来提高安全性.
- 开发的流程过程是合成化学家工具箱中获取烯的宝贵补充.
更多相关视频
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
相关概念视频
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
