烯胺酮平台构建转化生物质产品Cyrene为增值化合物

doi:10.6023/cjoc202212002

有机化学 ›› 2023, Vol. 43 ›› Issue (6): 2096-2103.DOI: 10.6023/cjoc202212002 上一篇下一篇

研究论文

烯胺酮平台构建转化生物质产品Cyrene为增值化合物

黄丽珠^a, 刘云云^a^,^*(), 万结平^a^,^b^,^*()

a 江西师范大学化学化工学院国家单糖化学合成工程技术研究中心南昌 330022
b 南京林业大学林产化学与材料国际创新高地南京 210037

收稿日期:2022-12-03 修回日期:2023-01-06 发布日期:2023-01-18
基金资助:
国家自然科学基金(22161022)

Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction

Lizhu Huang^a, Yunyun Liu^a,*(), Jieping Wan^a^,^b,*()

a National Engineering Research Center for Carbohydrate Synthesis, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
b International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037

Received:2022-12-03 Revised:2023-01-06 Published:2023-01-18
Contact: * E-mail: chemliuyunyun@jxnu.edu.cn; wanjieping@jxnu.edu.cn
Supported by:
National Natural Science Foundation of China(22161022)

文章分享

1. 232096S.pdf(2727KB)

摘要/Abstract

发展了在二氢左旋葡萄糖酮(Cyrene, 昔兰尼)的酮α-位烯胺化构建烯胺昔兰尼(EC)的方法, 有效地构建烯胺Cyrene作为平台合成子为将生物质产品Cyrene转化为增值化学品开辟了广阔的空间. 在此研究中, 实现了将烯胺昔兰尼向多种不同的手性有机衍生物, 包括NH-/N,N-双取代结构的烯胺昔兰尼, 氰基烯-和烯基磷修饰的昔兰尼, 呋喃稠环结构的昔兰尼以及2,2-二氟二氢呋喃稠合的昔兰尼的转化.

关键词: 昔兰尼, 生物质产品, 烯胺化, 平台, 增值

The enamination of Cyrene in the ketone α-site leading to the enamino Cyrene (EC) has been developed. The practical preparation of EC as a platform synthon opens broad space of chemical transformation for Cyrene biomass feedstock in the synthesis of diverse value-added chemicals. In the present work, the transformation of the EC for the synthesis of many different chiral organic derivatives, including NH-/N,N-disubstituted ECs, the cyanoalkenyl- and vinyl phosphine oxide-elabo- rated Cyrene, Cyrene fused furan, and 2,2-difluorodihydrofuran fused Cyrene, has been realized.

Key words: Cyrene, biomass feedstock, enamination, platform, value-added

引用此文

黄丽珠, 刘云云, 万结平. 烯胺酮平台构建转化生物质产品Cyrene为增值化合物[J]. 有机化学, 2023, 43(6): 2096-2103.

Lizhu Huang, Yunyun Liu, Jieping Wan. Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2096-2103.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 4

参考文献 19

[1]	(a) Sherwood, J.; De bruyn, M.; Constantinou, A.; Moity, L.; McElroy, C. R.; Farmer, T. J.; Duncan, T.; Raverty, W.; Hunt, A. J.; Clark, J. H. Chem. Commun. 2014, 50, 9650. doi: 10.1039/C4CC04133J pmid: 19533728
	(b) Craythorne, S. J.; Anderson, K.; Lorenzini, F.; McCausland, C.; Smith, E. F.; Licence, P.; Marr, A. C.; Marr, P. C. Chem.-Eur. J. 2009, 15, 7094. doi: 10.1002/chem.200801809 pmid: 19533728
	(c) De bruyn, M.; Fan, J.; Budarin, V. L.; Macquarrie, D. J.; Gomez, L. D.; Simister, R.; Farmer, T. J.; Raverty, W. D.; McQueen-Mason, S. J.; Clark, J. H. Energy Environ. Sci. 2016, 9, 2571. doi: 10.1039/C6EE01352J pmid: 19533728
	(d) Miura, M.; Kaga, H.; Yoshida, T.; Ando, K. J. Wood Sci. 2001, 47, 502. doi: 10.1007/BF00767906 pmid: 19533728
	(e) Sui, X.-W.; Wang, Z.; Liao, B.; Zhang, Y.; Guo, Q.-X. Bioresour. Technol. 2012, 103, 466. doi: 10.1016/j.biortech.2011.10.010 pmid: 19533728
[2]	See also information in Merck product introduction: https://www.merckgroup.com/en/research/science-space/envisioning-tomorrow/scarcity-of-resources/cyrene.html.
[3]	Camp, J. E. ChemSusChem 2018, 11, 3048. doi: 10.1002/cssc.201801420
[4]	(a) Duval, A.; Avérous, L. Green Chem. 2022, 24, 338. doi: 10.1039/D1GC03395F
	(b) Meng, X.; Pu, Y.; Li, M.; Ragauskas, A. J. Green Chem. 2020, 22, 2862. doi: 10.1039/D0GC00661K
	(c) Marathianos, A.; Liarou, E.; Hancox, E.; Grace, J. L.; Lester, D. W.; Haddleton, D. M. Green Chem. 2020, 22, 5833. doi: 10.1039/D0GC02184A
	(d) Gao, F.; Bai, R.; Ferlin, F.; Vaccaro, L.; Li, M.; Gu, Y. Green Chem. 2020, 22, 6240. doi: 10.1039/D0GC02149K
	(e) Brouwer, T.; Schuur, B. ACS Sustainable Chem. Eng. 2020, 8, 14807. doi: 10.1021/acssuschemeng.0c04159
[5]	(a) Bousfield, T. W.; Pearce, K. P. R.; Nyamini, S. B.; Angelis-Dimakis, A.; Camp, J. E. Green Chem. 2019, 21, 3675. doi: 10.1039/C9GC01180C
	(b) Mistry, L.; Mapesa, K.; Bousfield, T. W.; Jason, E. C. Green Chem. 2017, 19, 2123 doi: 10.1039/C7GC00908A
[6]	Yu, H.; Yu, D.; Xue, Z.; Zhang, B.; Mu, T. Chem. Eng. J. 2022, 431, 133397. doi: 10.1016/j.cej.2021.133397
[7]	(a) Wilson, K. L.; Kennedy, A. R.; Murray, J.; Greatrex, B.; Jamieson, C.; Watson, A. J. B. Beilstein J. Org. Chem. 2016, 12, 2005. doi: 10.3762/bjoc.12.187
	(b) Wilson, K. L.; Murray, J.; Jamieson, C.; Watson, A. J. B. Synlett 2018, 29, 650. doi: 10.1055/s-0036-1589143
[8]	Mention, M. M.; Flourat, A. L.; Peyrot, C.; Allais, F. Green Chem. 2020, 22, 2077. doi: 10.1039/D0GC00122H
[9]	Gonzalo, G. Biocatal. Biotransfor. 2022, 40, 252. doi: 10.1080/10242422.2021.1887150
[10]	Tamargo, R. J. I.; Rubio, P. Y. M.; Mohandoss, S.; Shim, J.-J.; Lee, Y. R. ChemSusChem 2021, 14, 2133. doi: 10.1002/cssc.v14.9
[11]	Ray, P.; Hughes, T.; Smith, C.; Hibbert, M.; Saito, K.; Simon, G. P. Polym. Chem. 2019, 10, 3334. doi: 10.1039/C9PY00353C pmid: 32237202
	(b) Diot-Néant, F.; Mouterde, L.; Fadlallah, S.; Miller, S. A.; Allais, F. ChemSusChem 2020, 13, 2613. doi: 10.1002/cssc.202000680 pmid: 32237202
[12]	De bruyn, M.; Budarin, V. L.; Misefari, A.; Shimizu, S.; Fish, H.; Cockett, M.; Hunt, A. J.; Hofsteffter, H.; Weckhuysen, B. M.; Clark, J. H.; Macquarrie, D. J. ACS Sustainable Chem. Eng. 2019, 7, 7878. doi: 10.1021/acssuschemeng.9b00470
[13]	Bonneau, G.; Peru, A. A. M.; Flourat, A. L.; Allais, F. Green Chem. 2018, 20, 2455. doi: 10.1039/C8GC00553B
[14]	Krishna, S. H.; McClelland, D. J.; Rashke, Q. A.; Dumesic, J. A.; Huber, G. W. Green Chem. 2017, 19, 1278. doi: 10.1039/C6GC03028A
[15]	Hughes, L.; McElroy, C. R.; Whitwood, A. C.; Hunt, A. J. Green Chem. 2018, 20, 4423. doi: 10.1039/C8GC01227J
[16]	Alhifthi, A.; Harris, B. L.; Goerigk, L.; White, J. M.; Williams, S. J. Org. Biomol. Chem. 2017, 15, 10105. doi: 10.1039/c7ob02499a pmid: 29170781
[17]	(a) Wang, Z.; Zhao, B.; Liu, Y.; Wan, J.-P. Adv. Synth. Catal. 2022, 364, 1508. doi: 10.1002/adsc.v364.9
	(b) Zheng, X.; Liu, Y.; Wan, J.-P. Chin. J. Org. Chem. 2021, 41, 2700. doi: 10.6023/cjoc202104053
	(c) Guo, H.; Liu, Y.; Wen, C.; Wan, J.-P. Green Chem. 2022, 24, 5058. doi: 10.1039/D2GC01644C
	(c) Fu, L.; Xu, W.; Pu, M.; Wu, Y-D.; Liu, Y.; Wan, J.-P. Org. Lett. 2022, 24, 3003. doi: 10.1021/acs.orglett.2c00912
	(d) Guo, Y.; Liu, Y.; Wan, J.-P. Chin. Chem. Lett. 2022, 33, 855. doi: 10.1016/j.cclet.2021.08.003
	(d) Yu, Q.; Liu, Y.; Wan, J.-P. Chin. Chem. Lett. 2021, 32, 3514. doi: 10.1016/j.cclet.2021.04.037
	(e) Duan, X.; Li, H.; Li, W.; Wang, J.; Liu, N. ChemistrySelect 2021, 6, 6478. doi: 10.1002/slct.v6.25
	(f) Zhang, B.; Fu, Z.; Yang, H.; Liu, D.; Sun, Y.; Xu, Y.; Yu, F.; Yan, S. Adv. Synth. Catal. 2022, 364, 1602. doi: 10.1002/adsc.v364.9
	(g) Fu, R.; Liu, Y.; Wu, T.; Zhang, X.; Zhu, Y.; Luo, J.; Zhang, Z.; Jiang, Y. Chem. Commun. 2022, 58, 3525. doi: 10.1039/D2CC00169A
	(h) Wu, Y.; Du, J.; Hao, W.; Jiang, B. Chin. J. Org. Chem. 2021, 41, 1563. (in Chinese) doi: 10.6023/cjoc202102018
	(吴亚男, 杜建宇, 郝文娟, 姜波, 有机化学, 2021, 41, 1563.) doi: 10.6023/cjoc202102018
	(i) Xie, Y.-Y.; Wang, Y.-C.; Qu, H.-E.; Tan, X.-C.; Wang, H.-S.; Pan, Y.-M. Adv. Synth. Catal. 2014, 356, 3347. doi: 10.1002/adsc.201400315
[18]	CCDC 2201314 and 2201818 contain the crystallographic data associated with this work.
[19]	The relative configuration of the chiral centres in products 8 and 9 were assigned by NOE NMR analysis.

烯胺酮平台构建转化生物质产品Cyrene为增值化合物

Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 4

参考文献 19

相关文章 6

编辑推荐

相关统计

本文评价

Entry	Solvent	Time/h	T/℃	Yield^b/%
1	p-Xylene	6	100	32
2	Toluene	6	100	84
3	THF	6	100	66
4	DMF	6	100	n.r
5	EL	6	100	n.r
6	EtOH	6	100	n.r
7	i-PrOH	6	100	n.r
8	DMSO	6	100	n.r
9	Acetone	6	100	n.r
10	1,4-Dioxane	6	100	n.r
11	NMP	6	100	n.r
12	MeCN	6	100	n.r
13	Toluene	5	100	87
14	Toluene	4	100	89
15	Toluene	3	100	56
16	Toluene	4	110	77
17	Toluene	4	90	83
18	Toluene	4	80	53

[1]	廖旭, 王泽宇, 唐武飞, 林金清. 多孔有机聚合物用于化学固定二氧化碳的研究进展[J]. 有机化学, 2023, 43(8): 2699-2710.
[2]	张洪浩, 石枫. 2-吲哚甲醇平台分子参与的催化不对称反应研究进展[J]. 有机化学, 2022, 42(10): 3351-3372.
[3]	王胜辉, 关永风, 刘秀娟, 原信颖, 蔚广曦, 李银茹, 张雁冰, 宋健, 李雯, 张赛扬. 新型喹啉-吲哚衍生物的设计、合成及抗肿瘤活性研究[J]. 有机化学, 2021, 41(9): 3617-3624.
[4]	徐静, 范维刚, 波波维奇·弗洛伦斯, 葛诺伊夫, 顾彦龙. 多组分反应:丰富生物质基平台分子高值化转化路线的新策略[J]. 有机化学, 2019, 39(8): 2131-2138.
[5]	谢先涛, 景羽, 许胜, 丁凯. 6-取代-3-胺基雌激素的高效合成[J]. 有机化学, 2017, 37(3): 767-772.
[6]	张海峰, 杨军艳, 吴建新, 毛海舫, 孙小玲. 木质素氧化降解研究进展[J]. 有机化学, 2016, 36(6): 1266-1286.