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2012 , Vol. 32 >Issue 11: 2148 - 2153

DOI: https://doi.org/10.6023/cjoc201204010

研究简报

S-(2-乙酰苯基)-二甲基硫代氨基甲酸酯环合产物的确定

  • 戈俊 ,
  • 裘亚 ,
  • 王春丽 ,
  • Jesse Yang ,
  • 陈瑛
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  • a 复旦大学药学院 上海 201203;
    b Intern from Henry M. Gunn High School, Palo Alto, CA USA

收稿日期: 2012-04-11

  修回日期: 2012-07-24

  网络出版日期: 2012-08-06

基金资助

国家自然科学基金(Nos. 20272010, 30200348, 30873164)资助项目.

收起

Clarification on the Structure of Cyclization Product of S-2-Acetylphenyl Dimethylthiocarbamate

  • Ge Jun ,
  • Qiu Ya ,
  • Wang Chunli ,
  • Yang Jesse ,
  • Chen Ying
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  • a Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, China;
    b Intern from Henry M. Gunn High School, Palo Alto, CA USA

Received date: 2012-04-11

  Revised date: 2012-07-24

  Online published: 2012-08-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20272010, 30200348, 30873164).

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摘要

通过1H NMR, NOE和X-ray等方法, 确定了S-(2-乙酰苯基)-二甲基硫代氨基甲酸酯在NaH/DMF条件下的环合产物为苯并-2H-噻喃-2-酮, 而非文献报道的苯并-4H-噻喃-4-酮. 探讨了苯并-2H-噻喃-2-酮和苯并-4H-噻喃-4-酮结构在氢谱上的规律性差异.

关键词： 苯并-4H-噻喃-4-酮; 苯并-2H-噻喃-2-酮; 环合; S-(2-乙酰苯基)-二甲基硫代氨基甲酸酯

本文引用格式

戈俊 , 裘亚 , 王春丽 , Jesse Yang , 陈瑛 . S-(2-乙酰苯基)-二甲基硫代氨基甲酸酯环合产物的确定[J]. 有机化学, 2012 , 32(11) : 2148 -2153 . DOI: 10.6023/cjoc201204010

Abstract

The structure of cyclization product from the reaction of S-2-acetylphenyl dimethylthiocarbamate with NaH in DMF was clarified by 1H NMR, NOE and X-ray. It proved to be a benzo-2H-thiopyran-2-one instead of a benzo-4H- thiopyran-4-one reported in literature. The 1H MNR chemical shift data of seven benzo-2H-thiopyran-2-ones and benzo-4H- thiopyran-4-ones were discussed, which might be useful for distinguishing benzo-2H-thiopyran-2-ones from benzo-4H- thiopyran-4-ones.

Key words： benzo-4H-thiopyran-4-one; benzo-2H-thiopyran-2-one; cyclization; S-2-acetylphenyl dimethylthiocarbamate

参考文献

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[4] Xia, P.; Yin, Z. J.; Chen, Y.; Zhang, Q.; Zhang, B. N.; Xia, Y.; Yang, Z. Y.; Kilgore, N.; Wild, C.; Morris-Natschke, S. L.; Lee, K. H. Bioorg. Med. Chem. Lett. 2004, 12, 3341.

[5] Tang, J.; Qian, K. D.; Zhang, B. N.; Chen, Y.; Xia, P.; Yu, D. L.; Xia, Y.; Yang, Z. Y.; Chen, C. H.; Morris-Natschke, S. L.; Lee, K. H. Bioorg. Med. Chem. 2010, 18, 4363.

[6] Chen, Y.; Cheng, M.; Liu, F. Q.; Xia, P.; Qian, K. D.; Yu, D. L.; Xia, Y.; Yang, Z. Y.; Chen, C. H.; Morris-Natschke, S. L.; Lee, K. H. Bioorg. Med. Chem. 2011, 46, 4924.

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