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化合物（CFC），尤其是CFC-11，用于合成有机体中间体，功能性材料和生物活性化合物的CFC-11。这是从CFC-11与托丁基膦的反应获得的。在1999年，通过CFC-11与二苯基二硫化物的反应，以良好的产量制备了二氯氟甲基苯基硫硫基（1）。用过氧化氢30％氧化1的氧化为相应的磺酸2分，产量为79％。用锌减少了氟苯基苯基磺酮（3），这是合成含氟的药物（例如抗病毒剂和抗生素）的重要有机体中间体。这些化合物是通过实验简单和经济的方法制备的。其专利的应用正在准备中。与锌相当于2的降低2给出了80％的产率，与各种羰基化合物反应，给出了有趣的重排和加法产品。以及在Sanyo Shimbun（1999年10月20日）。我们还报道了上述亚洲化学大会的结果（台北，1999年11月）。

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）。