Study on the synthesis of (+)-oxocamphor

Di Zhang; Xiong Xie; Jinsheng Feng; Hongliang Wen

doi:10.6023/cjoc201506023

Study on the synthesis of (+)-oxocamphor

Di Zhang, Xiong Xie, Jinsheng Feng, Hongliang Wen^*

^*此作品的通讯作者

化学与化工学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 评论/辩论

1 引用（Scopus）

摘要

(+)-Oxocamphor is a metabolite of (+)-camphor in vivo, which is used to treat heart failure in clinic. However the present synthetic method has problems of long reaction time, serious pollution and low yield. In this paper we report an efficient synthesis of (+)-oxocamphor was reported via bromination, reduction, esterification, hydrolysis and oxidation using (+)-camphor as starting material. All the intermediates and (+)-oxocamphor were confirmed by ¹H NMR, IR and GC-MS. The absolute configuration of 3,9-dibromocamphor was also ascertained by X-ray diffraction analysis. The overall yield of these 6-step procedures was about 10%.

源语言	英语
页（从-至）	202-206
页数	5
期刊	Chinese Journal of Organic Chemistry
卷	36
期	1
DOI	https://doi.org/10.6023/cjoc201506023
出版状态	已出版 - 1 1月 2016

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Zhang, D., Xie, X., Feng, J., & Wen, H. (2016). Study on the synthesis of (+)-oxocamphor. Chinese Journal of Organic Chemistry, 36(1), 202-206. https://doi.org/10.6023/cjoc201506023

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title = "Study on the synthesis of (+)-oxocamphor",

abstract = "(+)-Oxocamphor is a metabolite of (+)-camphor in vivo, which is used to treat heart failure in clinic. However the present synthetic method has problems of long reaction time, serious pollution and low yield. In this paper we report an efficient synthesis of (+)-oxocamphor was reported via bromination, reduction, esterification, hydrolysis and oxidation using (+)-camphor as starting material. All the intermediates and (+)-oxocamphor were confirmed by 1H NMR, IR and GC-MS. The absolute configuration of 3,9-dibromocamphor was also ascertained by X-ray diffraction analysis. The overall yield of these 6-step procedures was about 10%.",

keywords = "(+)-oxocamphor, Single crystal, Synthesis",

author = "Di Zhang and Xiong Xie and Jinsheng Feng and Hongliang Wen",

note = "Publisher Copyright: {\textcopyright} 2016 Chinese Chemical Society & SIOC, CAS.",

year = "2016",

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doi = "10.6023/cjoc201506023",

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T1 - Study on the synthesis of (+)-oxocamphor

AU - Zhang, Di

AU - Xie, Xiong

AU - Feng, Jinsheng

AU - Wen, Hongliang

PY - 2016/1/1

Y1 - 2016/1/1

N2 - (+)-Oxocamphor is a metabolite of (+)-camphor in vivo, which is used to treat heart failure in clinic. However the present synthetic method has problems of long reaction time, serious pollution and low yield. In this paper we report an efficient synthesis of (+)-oxocamphor was reported via bromination, reduction, esterification, hydrolysis and oxidation using (+)-camphor as starting material. All the intermediates and (+)-oxocamphor were confirmed by 1H NMR, IR and GC-MS. The absolute configuration of 3,9-dibromocamphor was also ascertained by X-ray diffraction analysis. The overall yield of these 6-step procedures was about 10%.

AB - (+)-Oxocamphor is a metabolite of (+)-camphor in vivo, which is used to treat heart failure in clinic. However the present synthetic method has problems of long reaction time, serious pollution and low yield. In this paper we report an efficient synthesis of (+)-oxocamphor was reported via bromination, reduction, esterification, hydrolysis and oxidation using (+)-camphor as starting material. All the intermediates and (+)-oxocamphor were confirmed by 1H NMR, IR and GC-MS. The absolute configuration of 3,9-dibromocamphor was also ascertained by X-ray diffraction analysis. The overall yield of these 6-step procedures was about 10%.

KW - (+)-oxocamphor

KW - Single crystal

KW - Synthesis

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DO - 10.6023/cjoc201506023

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AN - SCOPUS:84960103689

SN - 0253-2786

VL - 36

SP - 202

EP - 206

JO - Chinese Journal of Organic Chemistry

JF - Chinese Journal of Organic Chemistry

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ER -

Study on the synthesis of (+)-oxocamphor

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