Utilization of Chlorofluorocarbons (CFCs) : Synthesis of Medicines from Abandoned

氯氟烃 (CFC) 的利用：利用废弃材料合成药物

• 批准号: 10650834
• 负责人: TSUBOI Sadao
• 金额: $ 2.3万
• 依托单位: OKAYAMA UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1998
• 资助国家: 日本
• 起止时间: 1998 至 1999
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-10650834/
• 关键词: trichlorofluoromethane; abandoned chlorofluorocarbon; medicine; reagent for fluorination; biologically active compound; fluoromethyl phenyl sulfone; diphenyl disulfide; chlorofluoromethyl phenyl sulfone; フェニルジスルフィド; クロロフルオロメチルフェニルスホン; フロン11; トリ

The aim of the present research is the utilization of chlorofluorocarbons (CFCs), especially CFC-11 for the synthesis of organointermediates, functional materials and biologically active compounds without decomposition.In 1998, we succeeded in the synthesis of propargyl alcohols via basic treatment of fluoroethylenes, which were obtained from the reaction of CFC-11 with tributylphosphine.In 1999, dichlorofluoromethyl phenyl sulfid (1) was prepared in a good yield by the reaction of CFC-11 with diphenyl disulfide. Oxidation of 1 with 30% hydrogen peroxide gave the corresponding sulfone 2 in 79% yield. Reduction of 2 with zinc afforded fluoromethyl phenyl sulfone (3) , which is an important organointermediate for the synthesis of fluorine-containing medicines such as antivirus agents and antibiotics.These compounds were prepared by experimentally simple and economical methods. The application of its patent is under preparation. Reduction of 2 with an equivalent of zinc gave chlorofluoromethyl phenyl sulfone in 80% yield, which reacted with various carbonyl compounds, giving interesting rearrangement and addition products.These results were reported to all of Japan in Yomiuri Shimbun (October 18 and 19, 1999) and also in Sanyo Shimbun (October 20, 1999). We also reported the above results in Asian Chemical Congress (Taipei, November 1999).

本研究的目的是利用氯氟烃（CFC-11）不分解地合成有机中间体、功能材料和生物活性化合物。1998年，我们成功地用CFC-11与三丁基膦反应得到的氟代乙烯经碱处理合成了炔丙醇。1999年，我们成功地利用CFC-11与三丁基膦反应得到的氟代乙烯合成了炔丙醇。二氯氟甲基苯硫醚（1）是由CFC-11与二苯二硫醚反应制得的。用30%过氧化氢氧化1得到相应的砜2，产率为79%。用锌还原2得到氟甲基苯砜（3），它是合成抗病毒药物和抗生素等含氟药物的重要有机中间体，这些化合物的制备方法简单，成本低。其专利申请正在准备中。用等量的锌还原2得到氯氟甲基苯砜，产率为80%，它与各种羰基化合物反应，得到有趣的重排和加成产物。这些结果在读卖新闻（1999年10月18日和19日）和三洋新闻（1999年10月20日）上向全日本报道。我们也在1999年11月台北举行的亚洲化学大会上报告了上述结果。

项目成果

Kentaro Kataoka and Sadao Tsuboi,: "Generation of Acetylides by Treatment of Fluoroethylenes with LDA : Preparation of Propargyl Alcohols"Synthesis. (in press). (2000)

Kentaro Kataoka 和 Sadao Tsuboi，：“用 LDA 处理氟乙烯生成乙酰化物：丙炔醇的制备”合成。

Kentaro Kataoka and Sadao Tsuboi: "Generation of Acetylides by Treatment of Fluoroethylenes with LDA : Preparation of Propargyl Alcohols"Synthesis. 2000 (in press). (2000)

Kentaro Kataoka 和 Sadao Tsuboi：“用 LDA 处理氟乙烯生成乙酰化物：丙炔醇的制备”合成。

坪井貞夫: "フロン11からプロパギルアルコール誘導体の製造" 日本特許公開公報. (1998)

Sadao Tsuboi：“从 Freon-11 生产炔丙醇衍生物”日本专利公开（1998 年）。