Chin. J. Org. Chem. ›› 1998, Vol. 18 ›› Issue (6): 532-537. Previous Articles     Next Articles

Original Articles

光学活性N-肉桂酰R(S)-4-异丙基四氢噻唑-2-硫酮的合成及其 量子化学的研究

李叶芝;郭纯孝;鲁向阳;赵晓刚;黄化民   

  1. 吉林大学化学系.长春(130023);理论化学计算国家重点实验室
  • 发布日期:1998-12-25

Study on synthesis and quantum chemistry of R(S)-N-cinnamyl-4- isopropyl thiazolidine-2-thione

Li Yezhi;Guo Chunxiao;Lu Xiangyang;Zhao Xiaogang;Huang Huamin   

  1. Jilin Univ, Dept Chem.Changchun(130023)
  • Published:1998-12-25

Aminoalcohols R-3-methyl-2-amino-butyl alcohol 2a [α]^2^0~D -15.18° , S-3-methyl-2-amino-butyl alcohol 2b [α]^2^0~D +16.96° were prepared by the reduction of D or L-valine methyl ester. The reduction was carried out the KBH~4 and CaCl~2. R-4- isopropylthiazolidine-2-thione 3a, [α]^2^0~D +37.00° and S-4- isopropylthiazolidine-2-thione 3b, [α]^2^0~D -36.90° were obtained by refluxing a solution of R or S-3-methyl-2-aminobutylalcohol, CS~2 and KOH. The R-N-cinnamyl-4-isopropyl thiazolidine-2-thione 4a, [α] ^2^0~D -169.72° and S-N-cinnamyl-4-isopropylthiazolidine-2- thione 4b, [α]^2^0~D +173.20° was easily prepared by dehydro chlorination between cinnamyl chloride and R or S-4-isopropylthia- zolidine-2- thione under the presence of Et~3N. The electronic structure of products and reactants were studied by molecular orbital PM3 method. The reaction enthalpies and optimized configuration for products were obtained.

Key words: CHARGE DISTRIBUTION, THIAZOLE P, REACTION MECHANISM, CONFIGURATION, SYNTHESIS, OPTIMIZATION, ELECTRONIC STRUCTURE, TETRAHYDRO- COMPOUNDS, THIAZOLONE P, THIOKETONE

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