Synthesis of α,β-Epoxy Ketones in a Water Suspension Medium

Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (08): 969-971. Previous Articles Next Articles

Original Articles

水悬浮体系中α,β-环氧酮类化合物的合成研究

王永灿，叶金星，梁鑫淼*

(中国科学院大连化学物理研究所大连 116011)

收稿日期:2004-07-14 修回日期:2005-03-05 发布日期:2005-07-30
通讯作者: 梁鑫淼

Synthesis of α,β-Epoxy Ketones in a Water Suspension Medium

WANG Yong-Can,YE Jin-Xing,LIANG Xin-Miao*

(Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116011)

Received:2004-07-14 Revised:2005-03-05 Published:2005-07-30
Contact: LIANG Xin-Miao

Abstract

Trichloroisocyanuric acid-base can be used as an efficient oxidant for the epoxidaiton of enones and tandem oxidation-epoxidation of allylic alcohols in a water-suspension system as completely organic solvent free reactions. The effects of surfactant and base have been investigated. For most of the enones and allylic alcohols, the reaction could be completed within several hours with good yields.

Key words: allylic alcohol, trichloroisocyanuric acid, surfac-tant, α,β-enone, epoxidation

Cite this article

WANG Yong-Can,YE Jin-Xing,LIANG Xin-Miao*. Synthesis of α,β-Epoxy Ketones in a Water Suspension Medium[J]. Chin. J. Org. Chem., 2005, 25(08): 969-971.

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水悬浮体系中α,β-环氧酮类化合物的合成研究

Synthesis of α,β-Epoxy Ketones in a Water Suspension Medium

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[1]	Biao Han, Yaoyao Zhang, Shuhan Chen, Mengge Zhao, Nan Li, Weishuang Li, Lei Zhu. Preparation of Axially Grafted Temperature-Responsive Chiral Salen Mn^III and Application in Asymmetric Epoxidation of Olefins in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 244-253.
[2]	Weiwei Wang, Yu Zhao, Xinlei Liu, Jiazhen Jiang, Ming'an Wang. Synthesis and Antifungal Activity of 3-Aryl-7-methyl- 7-hydroxy-2-octen-6-olide [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2343-2353.
[3]	Hongbo Dong, Weiwei Wang, Yu Zhao, Xinlei Liu, Ming'an Wang. Synthesis and Antifungal Activity of 3,7-Dimethyl-7-hydroxy-2-octen-6-olide Analogues [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1646-1657.
[4]	Jiahao Liu, Shidong Zhang, Zihong Luan, Yan Liu, Zhuofeng Ke. Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4361-4369.
[5]	Gucheng Yuan, Jiawei Liu, Shihang Yu, Chaonan Yuan, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of (3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene, Sex Pheromone Component of Hyphantria cunea [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4437-4443.
[6]	Ma Xiantao, Yu Jing, Wang Zilong, Zhang Yun, Zhou Qiuju. Efficient Activation of Allylic Alcohols in Pd-Catalyzed Allylic Substitution Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2669-2677.
[7]	Qi Lianshan, Wang Tao, Wei Yongmei, Tian Hengshui. Study on the Effect of Co-reductant Aldehydes on Epoxidation of Propylene Catalyzed by Metalloporphyrins [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1305-1309.
[8]	Zong Wuzhong, Hu Yulai, Wang Xiaoping, Liu Jiaxin, Huang Danfeng, Wang Kehu. Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source [J]. Chin. J. Org. Chem., 2019, 39(5): 1396-1403.
[9]	Ma Xiantao, Yu Jing, Ma Ruitian, Yan Ran, Zhang Zhenlei. Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols [J]. Chin. J. Org. Chem., 2019, 39(3): 830-835.
[10]	Sun Moran, Dai Lei, Yang Hua, Liu Hongmin, Yu Dequan. Enantioselective Synthesis of Core Structures of Hydramicromelins A, B and C [J]. Chin. J. Org. Chem., 2018, 38(9): 2443-2449.
[11]	Su Yingpeng, Shi Ya, Chang Bingbing, Wu Lili, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source [J]. Chin. J. Org. Chem., 2018, 38(6): 1454-1461.
[12]	Zou Xiaochuan, Shi Kaiyun, Li Jun, Wang Yue, Wang Cun, Deng Chaofang, Ren Yanrong, Tan Jun, Fu Xiangkai. Research Progress on Epoxidation of Olefins Catalyzed by Mn(II, III, V) in Different Valence States [J]. Chin. J. Org. Chem., 2016, 36(8): 1765-1778.
[13]	Zhu Qingying, Shen Haimin, Ji Hongbing. Asymmetric Epoxidation of trans-Chalcone by H₂O₂ Induced by β-Cyclodextrin Derivatives in Water [J]. Chin. J. Org. Chem., 2016, 36(8): 1907-1914.
[14]	Zhong Yexin, Ren Kai, Xie Xiaomin, Zhang Zhaoguo. Transition Metal Catalyzed Isomerization Reaction of Allylic Alcohols [J]. Chin. J. Org. Chem., 2016, 36(2): 258-273.
[15]	Zhang Jian, Wang Heng, Ren Shaobo, Zhang Wenxia, Liu Yunkui. Cu(0)/Selectfluor System-Catalyzed Epoxidation of Chalcone Compounds [J]. Chin. J. Org. Chem., 2015, 35(12): 2650-2654.