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首頁 / 所有 / 行業(yè)資訊 / 秒級反應(yīng)，高產(chǎn)率

！連續(xù)流微反應(yīng)技術(shù)助力重氮化高效合成炔基化合物

秒級反應(yīng)
，高產(chǎn)率！連續(xù)流微反應(yīng)技術(shù)助力重氮化高效合成炔基化合物

2025/7/30

炔基是有機(jī)化學(xué)中用途廣泛的官能團(tuán)

，它的合成價(jià)值主要是生成新的C-C和C-X（X = O

，N，S）鍵以及用于加成

，環(huán)加成和過渡金屬催化的交叉偶聯(lián)反應(yīng)等

，是合成藥物分子

、功能材料、天然產(chǎn)物及精細(xì)化學(xué)品的重要途徑

。然而

，傳統(tǒng)的間歇式炔基化反應(yīng)常面臨產(chǎn)率波動(dòng)大、放大困難

、副產(chǎn)大量有害N?O氣體等問題

，制約了其工業(yè)化應(yīng)用潛力。

針對以上問題

，都柏林大學(xué)Marcus Baumann教授利用連續(xù)流技術(shù)

，采用重氮化條件提出了一種創(chuàng)新的異惡唑酮合成炔的策略。該方法成功克服了產(chǎn)率不穩(wěn)定

、安全生產(chǎn)等難題

，并且在較短時(shí)間內(nèi)高效制備多種炔烴產(chǎn)物。

連續(xù)流重氮化高效合成炔烴——以異惡唑酮為例

異惡唑酮是指一類含有異惡唑環(huán)

，并在環(huán)上特定位置帶有羰基（C=O）的有機(jī)化合物

，在藥物化學(xué)、農(nóng)藥化學(xué)和材料科學(xué)中應(yīng)用廣泛

。本研究以異惡唑-5-酮（isoxazole-5-one）為模版底物

，在連續(xù)流微反應(yīng)器中進(jìn)行炔基化反應(yīng)優(yōu)化。

圖1 流程模式下的炔合成裝置

原料配制：將異惡唑-5-酮（1當(dāng)量）溶解在乙酸（0.1 M）中

，制備炔基化所需的溶劑

。

反應(yīng)儀器配制：亞硝酸鈉和底物通過進(jìn)料泵分別進(jìn)入流動(dòng)反應(yīng)器，實(shí)現(xiàn)高效的炔基化反應(yīng)（圖1）

。

產(chǎn)品分析：反應(yīng)液收集于飽和碳酸氫鈉水溶液中

。經(jīng)有機(jī)溶劑萃取、干燥后

，以柱層析方法純化產(chǎn)品

，以評估反應(yīng)產(chǎn)率。

沈氏科技微反應(yīng)器

關(guān)鍵工藝優(yōu)化與結(jié)果

該研究重點(diǎn)考察了反應(yīng)溫度

、反應(yīng)溶劑體系

、亞硝酸鈉用量和添加劑等關(guān)鍵參數(shù)，最終確定的最優(yōu)工藝條件如下

。

反應(yīng)條件：在25 ℃

、NaNO₂與底物摩爾比為2、FeSO₂·7 H₂O與底物摩爾比為2

、AcOH/H₂O （v/v=5:1）的條件下

，原料轉(zhuǎn)化率大于90%。

優(yōu)化結(jié)果：當(dāng)?shù)孜锶芤海?.1 M）流速為0.61 mL/min，亞硝酸鈉水溶液（2 M）流速為3.04 mL/min時(shí)

，產(chǎn)品的收率達(dá)到61%

，且反應(yīng)停留時(shí)間僅需35秒，效率相比傳統(tǒng)間歇反應(yīng)提升數(shù)十倍

。

工藝普適性驗(yàn)證

優(yōu)化后的連續(xù)流工藝成功應(yīng)用于含異惡唑結(jié)構(gòu)化合物的合成中（圖2），證明了該工藝具有良好的底物適用性

，能夠高效

、穩(wěn)定地獲得多種目標(biāo)炔烴產(chǎn)物。

圖2 在流動(dòng)模式下具有產(chǎn)量的底物范圍

克級放大與生產(chǎn)力優(yōu)勢

該工藝的一個(gè)關(guān)鍵優(yōu)勢在于其放大潛力：使用Vapourtec E-Series流動(dòng)反應(yīng)器（蠕動(dòng)泵）替代注射泵

，實(shí)現(xiàn)大體積進(jìn)料。以1 g底物規(guī)模合成2a, 2c, 2l

，產(chǎn)率與小試相當(dāng)（43-57%）

，生產(chǎn)力達(dá)1.7-2.1 g/h。

連續(xù)流 vs. 傳統(tǒng)間歇反應(yīng)

本研究開發(fā)的連續(xù)流炔烴合成工藝

，有效克服了傳統(tǒng)間歇反應(yīng)的局限

，展現(xiàn)出以下優(yōu)勢。

該研究為異噁唑酮轉(zhuǎn)化為高附加值炔烴提供了可規(guī)?div id="m50uktp" class="box-center"> ；?div id="m50uktp" class="box-center"> 、本質(zhì)安全且高效的解決方案，印證了連續(xù)流微反應(yīng)技術(shù)在應(yīng)對復(fù)雜有機(jī)合成挑戰(zhàn)

、推動(dòng)綠色安全化工生產(chǎn)方面的潛力

。

沈氏科技微連續(xù)流撬裝系統(tǒng)

沈氏科技子公司微智源，專注微連續(xù)流技術(shù)領(lǐng)域十余年

，已成功服務(wù)于醫(yī)藥

、農(nóng)藥、染料

、新能源材料等多個(gè)領(lǐng)域

，助力企業(yè)解決合成難題，促進(jìn)實(shí)驗(yàn)室創(chuàng)新成果向規(guī)?div id="jpandex" class="focus-wrap mb20 cf">；?div id="jpandex" class="focus-wrap mb20 cf">、商業(yè)化生產(chǎn)的轉(zhuǎn)化。

參考文獻(xiàn)：Org. Biomol. Chem., 2025,23, 1314-1319

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