物理化学学报 >> 2008, Vol. 24 >> Issue (06): 955-960.doi: 10.3866/PKU.WHXB20080606

研究论文 上一篇    下一篇

BPOB的绝对不对称合成机理及固体CD光谱

宣为民; 邹方; 陈雷奇; 方雪明; 连伟; 章慧   

  1. 厦门大学化学化工学院化学系, 固体表面物理化学国家重点实验室, 福建 厦门 361005
  • 收稿日期:2008-01-21 修回日期:2008-03-14 发布日期:2008-06-03
  • 通讯作者: 连伟; 章慧 E-mail:huizhang@xmu.edu.cn;lianwei@xmu.edu.cn

Mechanism of Absolute Asymmetric Synthesis and Solid-State CD Spectroscopy of BPOB

XUAN Wei-Min; ZOU Fang; CHEN Lei-Qi; FANG Xue-Ming; LIAN Wei; ZHANG Hui   

  1. State Key Laboratory for Physical Chemistry of Solid Surface, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, P. R. China
  • Received:2008-01-21 Revised:2008-03-14 Published:2008-06-03
  • Contact: LIAN Wei; ZHANG Hui E-mail:huizhang@xmu.edu.cn;lianwei@xmu.edu.cn

摘要: 以苯乙酮与间苯二甲酸甲酯为原料经由Claisen缩合制备了1,3-二(3-苯基-3-氧代丙烯醇)苯(BPOB). 用元素分析、MS、1H NMR、UV吸收光谱、X射线单晶衍射和固体CD光谱等对其进行了表征. 晶体结构数据显示, BPOB属于Sohncke空间群P212121, UV和1H NMR谱表明, BPOB在溶液中主要以烯醇式存在, 固体CD光谱和重结晶实验证明, BPOB手性晶体的形成是结晶诱导的绝对不对称合成.

关键词: 1,3-二(3-苯基-3-氧代丙烯醇)苯, 手性对称性破缺, 绝对不对称合成, 手性晶体, 固体CD光谱

Abstract: 1,3-bis (3-phenyl-3-oxopropanoyl)benzene (BPOB) was prepared by Claisen condensation of acetophenone and dimethyl isophthalate and characterized by elemental analysis, MS, 1H NMR, UV absorption spectrum, solid-state circular dichroism(CD) spectra, and X-ray single-crystal diffraction. The X-ray crystallographic data indicated that BPOB crystallized in a Sohncke group P212121, UV and 1H NMR showed that the enol tautomer was the most dominant form in solution, and the solid-state CD spectra and repeated recrytallization revealed that the formation of chiral BPOB crystals could be regarded as crystallization-induced asymmetric synthesis.

Key words: 1,3-Bis(3-phenyl-3-oxopropanoyl)benzene, Chrial symmetry breaking, Absolute asymmetric synthesis, Chiral crystal, Solid-state circular dichroismspectroscopy

MSC2000: 

  • O641.6