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有机化学
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有机化学 ›› 2018, Vol. 38 ›› Issue (2): 519-525.DOI: 10.6023/cjoc201708011 上一篇    下一篇

研究简报

环苯基六炔烃的制备:脱Ph2P(O)/分子内Eglington偶联环化反应

彭丽芬a, 张思维a, 王丙昊a, 寻梦硕a, 唐子龙a, 焦银春a, 许新华b   

  1. a 湖南科技大学理论有机化学与功能分子教育部重点实验室 精细聚合物可控制备及功能化应用湖南省重点实验室 化学化工学院 湘潭 411201;
    b 湖南大学化学化工学院 化学生物传感与计量学国家重点实验室 长沙 410082
  • 收稿日期:2017-08-07 修回日期:2017-09-28 发布日期:2017-10-20
  • 通讯作者: 彭丽芬, 唐子龙 E-mail:1060137@hnust.edu.cn;zltang@hnust.edu.cn
  • 基金资助:

    湖南省教育厅一般项目（No.17C0629）、湖南科技大学博士启动基金（No.E51693）、湖南科技大学理论有机化学与功能分子教育部重点实验室开放基金（No.E21630）和国家自然科学基金（No.21402048）资助项目.

Synthesis of Cyclic Phenyl Polyynes: Ph2P-Deprotection/Intramolecular Eglington Coupling Cyclization

Peng Lifena, Zhang Siweia, Wang Binghaoa, Xun Mengshuoa, Tang Zilonga, Jiao Yinchuna, Xu Xinhuab   

  1. a Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201;
    b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2017-08-07 Revised:2017-09-28 Published:2017-10-20
  • Contact: 10.6023/cjoc201708011 E-mail:1060137@hnust.edu.cn;zltang@hnust.edu.cn
  • Supported by:

    Project supported by the General Project of Hunan Education Department (No. 17C0629), the Doctoral Foundation of Hunan University of Science and Technology (No. E51693), the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology (No. E21630) and the National Natural Science Foundation of China (No. 21402048).

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补充材料

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脱二苯膦酰（Ph2P（O））保护基/分子间炔烃偶联环化反应可一锅进行，高效形成环苯基六炔烃.与Haley等的脱硅基/Eglington偶联分步反应的制备方法相比，极性Ph2P（O）保护基使产物与少量剩余原料具有不同极性而易分离，且本反应与产物Rf值相近的分子间偶联副产物量较少，使得产物易分离.且一锅反应可避免脱Ph2P（O）的后处理，减少化合物损失，有效提高了环苯基六炔烃的产率.此外，本方法还具有中间体易制备、反应条件温和等优点.

关键词: 一锅反应, 二苯基膦酰基保护基, 环苯基多炔烃

Ph2P (O)-deprotection/intramolecular Eglington coupling cyclization, proceeding in one-pot manner, can be applied to synthesize cyclic phenyl polyynes. Compared to Micheal M. Haley's stepwise desilylation/Eglington coupling reaction, the polar Ph2P (O) protecting group enabled facile seperation of product from remaining starting compound for their different polarity, and it also led to easy separation of target compound because the amont of by-products which showed similar Rf to target compound decreased. Furthermore, our one-pot reaction, avoiding the workup after Ph2P (O)-deprotection and reducing losses of materials, increased the yield of cyclic aromatic polyynes. This method showed some other outstanding features including easy synthesis of intermediates and mild reaction conditions.

Key words: one-pot reaction, diphenylphosphoryl protecting group, cyclic phenyl polyyne