A study on the allylic oxidation of some β-rose ketones
A study on the allylic oxidation of β-rose ketones was conducted. The oxo-derivatives of three representative rose ketones β-damascone, β-damascenone and β-ionone were synthesized by using Rh-catalyzed allylic oxidation in good yields at room temperature in the presence of tert-butyl hydroperoxide....
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| Format: | Article |
| Language: | English |
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Elsevier
2025-07-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715625004278 |
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| author | Deshou Mao Shihua Zhu Yafen Zhao Wenwen Zhang Ruilin Hu Bingbiao Cai Cenming Zhu Ankun Zhou Jianfeng Li |
| author_facet | Deshou Mao Shihua Zhu Yafen Zhao Wenwen Zhang Ruilin Hu Bingbiao Cai Cenming Zhu Ankun Zhou Jianfeng Li |
| author_sort | Deshou Mao |
| collection | DOAJ |
| description | A study on the allylic oxidation of β-rose ketones was conducted. The oxo-derivatives of three representative rose ketones β-damascone, β-damascenone and β-ionone were synthesized by using Rh-catalyzed allylic oxidation in good yields at room temperature in the presence of tert-butyl hydroperoxide. Some typical oxidants for allylic oxidation were screened to compare with the Rh-catalyzed reaction by using HPLC analysis (external standard method). The conventional oxidants, i.e. CrO3 and SeO2 with different modified conditions gave generally inferior yields. These results indicated that this method exhibited high efficiency and good selectivity in the oxidation of β-rose ketones. The presence of water played an important role in promoting the oxidation reaction. The Rh-catalyzed reactions can be conducted under mild, environment friendly reaction conditions, very low loading of catalyst and the possibility of repeated use of Rh-catalyst, making it a competitive method for large scale preparations of such fragrances. |
| format | Article |
| id | doaj-art-9080430f487548e5bd113cbcb5ea9e40 |
| institution | DOAJ |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-9080430f487548e5bd113cbcb5ea9e402025-08-20T03:23:34ZengElsevierResults in Chemistry2211-71562025-07-011610244410.1016/j.rechem.2025.102444A study on the allylic oxidation of some β-rose ketonesDeshou Mao0Shihua Zhu1Yafen Zhao2Wenwen Zhang3Ruilin Hu4Bingbiao Cai5Cenming Zhu6Ankun Zhou7Jianfeng Li8R & D Center, China Tobacco Yunnan Industrial Co. Ltd, Kunming 650231, ChinaIntegrated Planning Department, China Tobacco Yunnan Industrial Co. Ltd, Kunming 650231, ChinaSchool of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicinal Utilization, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Chenggong District, Kunming 650106, PR ChinaSchool of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicinal Utilization, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Chenggong District, Kunming 650106, PR ChinaR & D Center, China Tobacco Yunnan Industrial Co. Ltd, Kunming 650231, ChinaR & D Center, China Tobacco Yunnan Industrial Co. Ltd, Kunming 650231, ChinaR & D Center, China Tobacco Yunnan Industrial Co. Ltd, Kunming 650231, ChinaYunnan Shureli Biopharma Co. Ltd, 285 Xinguang Alley, Wuhua District, Kunming 650231, Yunnan, PR ChinaSchool of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicinal Utilization, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Chenggong District, Kunming 650106, PR China; Corresponding author.A study on the allylic oxidation of β-rose ketones was conducted. The oxo-derivatives of three representative rose ketones β-damascone, β-damascenone and β-ionone were synthesized by using Rh-catalyzed allylic oxidation in good yields at room temperature in the presence of tert-butyl hydroperoxide. Some typical oxidants for allylic oxidation were screened to compare with the Rh-catalyzed reaction by using HPLC analysis (external standard method). The conventional oxidants, i.e. CrO3 and SeO2 with different modified conditions gave generally inferior yields. These results indicated that this method exhibited high efficiency and good selectivity in the oxidation of β-rose ketones. The presence of water played an important role in promoting the oxidation reaction. The Rh-catalyzed reactions can be conducted under mild, environment friendly reaction conditions, very low loading of catalyst and the possibility of repeated use of Rh-catalyst, making it a competitive method for large scale preparations of such fragrances.http://www.sciencedirect.com/science/article/pii/S2211715625004278Rose ketones4-oxo-β-damascone6-oxo-β-damascenone4-oxo-iononeRhodium catalysisAllylic oxidation |
| spellingShingle | Deshou Mao Shihua Zhu Yafen Zhao Wenwen Zhang Ruilin Hu Bingbiao Cai Cenming Zhu Ankun Zhou Jianfeng Li A study on the allylic oxidation of some β-rose ketones Results in Chemistry Rose ketones 4-oxo-β-damascone 6-oxo-β-damascenone 4-oxo-ionone Rhodium catalysis Allylic oxidation |
| title | A study on the allylic oxidation of some β-rose ketones |
| title_full | A study on the allylic oxidation of some β-rose ketones |
| title_fullStr | A study on the allylic oxidation of some β-rose ketones |
| title_full_unstemmed | A study on the allylic oxidation of some β-rose ketones |
| title_short | A study on the allylic oxidation of some β-rose ketones |
| title_sort | study on the allylic oxidation of some β rose ketones |
| topic | Rose ketones 4-oxo-β-damascone 6-oxo-β-damascenone 4-oxo-ionone Rhodium catalysis Allylic oxidation |
| url | http://www.sciencedirect.com/science/article/pii/S2211715625004278 |
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