Flexible Synthesis of Enantiomeric and Racemic 3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinolines via Bischler-Napieralski Reaction
文献类型：期刊论文
| 作者 | Kang Chuan-qing; Du Zhi-jun; Wang Lan-lan; Chen Yu; Qiu Xue-peng; Guo Hai-quan; Gao Lian-xun |
| 刊名 | CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
 |
| 出版日期 | 2012-09-01 |
| 卷号 | 28期号:5页码:843-846 |
| 关键词 | Bischler-napieralski Reaction Racemerization 1 2 3 4-tetrahydroisoquinoline |
| ISSN号 | 1005-9040 |
| 英文摘要 | With methyl ester of N-acylated L-3-(3,4-dihydroxyphenyl)alanine(L-DOPA) as starting material, racemic derivatives of 3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline were obtained with cyclization by Bischler-Napieralski(BN) reaction followed by reduction of methyl ester group to hydroxymethyl, while the optical pure enantiomers were prepared by the reduction of the methyl ester group to hydroxymethyl prior to cyclization with BN reaction. Racemerization took place in the BN stage in the presence of methyl ester, an electron-withdrawing group adjacent to chiral center. Therefore, the sequence of synthetic stages of cyclization and reduction, and subsequently whether there is electron-withdrawing group or not determines the chiral optical activity of the products. |
| 语种 | 英语 |
| WOS记录号 | WOS:000312475400020 |
| 出版者 | HIGHER EDUCATION PRESS |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/49307]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Gao Lian-xun |
| 作者单位 | Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China |
| 推荐引用方式 GB/T 7714 | Kang Chuan-qing,Du Zhi-jun,Wang Lan-lan,et al. Flexible Synthesis of Enantiomeric and Racemic 3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinolines via Bischler-Napieralski Reaction[J]. CHEMICAL RESEARCH IN CHINESE UNIVERSITIES,2012,28(5):843-846. |
| APA | Kang Chuan-qing.,Du Zhi-jun.,Wang Lan-lan.,Chen Yu.,Qiu Xue-peng.,...&Gao Lian-xun.(2012).Flexible Synthesis of Enantiomeric and Racemic 3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinolines via Bischler-Napieralski Reaction.CHEMICAL RESEARCH IN CHINESE UNIVERSITIES,28(5),843-846. |
| MLA | Kang Chuan-qing,et al."Flexible Synthesis of Enantiomeric and Racemic 3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinolines via Bischler-Napieralski Reaction".CHEMICAL RESEARCH IN CHINESE UNIVERSITIES 28.5(2012):843-846. |
入库方式： OAI收割
来源：化学研究所
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