从o-Triazenylarylboronic 酸产生的阿里因与西洛的功能化
Motoki Ito1, Ryuhei Oda1, Akari Shoji1
1Meiji Pharmaceutical University.
Chemical & pharmaceutical bulletin
|May 22, 2024
概括
我们开发了一种新方法,使用arynes来功能化多面体的寡聚二氧化 (POSS) 和氧化. 这种技术允许用药物化合物对POSS进行高收益的修改,从而实现复杂的分子架构.
科学领域:
- 有机化学 有机化学
- 合成有机化学 合成有机化学
背景情况:
- 多面体寡二酸 (POSS) 是具有独特性质的多功能纳米级构建块.
- 对POSS的功能化对于开发先进材料和有针对性的疗法至关重要.
- 现有的POSS修改方法在范围或效率上可能受到限制.
研究的目的:
- 报告一种新的方法,用于POSS和相关的西洛的阿里因介导功能化.
- 为了证明POSS与制药核心的结合.
- 为了实现POSS的直角双重功能.
主要方法:
- 使用o-triazenylarylboronic酸作为阿里因前体.
- 用于凝作为一个激活剂,用于aryne生成和反应.
- 应用了该方法来功能化具有阿里诺菲尔侧链的锡洛干.
- 结合POSS与一个cabozantinib合成中间体通过一个aryne.
主要成果:
- 在不改变锡洛核心的情况下,实现了锡洛的高产量功能化.
- 成功将POSS与制药中间体结合在一起.
- 通过将阿里尼化学与惠斯根循环结合,证明了POSS的直角双重功能.
结论:
- 开发的aryne化学为POSS功能化提供了一条高效和多功能途径.
- 这种方法可以更容易地将制药部分纳入POSS,为药物输送系统开辟了道路.
- 正交的功能化策略允许构建基于POSS的复杂,多功能材料.
相关概念视频
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
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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,...
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02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
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Introduction
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.
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02:27Preparation of Alkynes: Alkylation Reaction
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03:08Hydroboration-Oxidation of Alkenes
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Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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