二氢左旋葡萄糖酮

二氢左旋葡萄糖酮
	IUPAC名; (1R,5S)-7,8-Dioxabicyclo[3.2.1]octan-2-one
别名	Cyrene
识别
CAS号	53716-82-8
PubChem	16762483
ChemSpider	9150700
SMILES	[C@H]12CCC([C@H](OC1)O2)=O;
EINECS	807-130-4
性质
化学式	C6H8O3
摩尔质量	128.13 g·mol−1
外观	澄清或黄色液体
密度	1.2508 g/cm3 (20 °C)
沸点	226 °C（499 K）
溶解性（水）	miscible
蒸氣壓	14.4 Pa (25 °C)
折光度n; D	1.4732 (20 °C)
危险性
	GHS危险性符号;
GHS提示词	警告
H-术语	H319
P-术语	P305+351+338, P313
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

二氢左旋葡萄糖酮是一种有机化合物，化学式为C₆H₈O₃。它是可生物降解的非质子偶极溶剂，是二甲基甲酰胺（DMF）和N-甲基吡咯烷酮（NMP）的环保替代品。^[2]

它可以用作一些有机反应中的溶剂，用来替代DMF，如门秀金反应、^[3]薗頭耦合反應、^[4]铃木反应^[5]以及尿素的合成^[6]。

参考文献[编辑]

^ ^1.0 ^1.1 ^1.2 Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville. Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds. International Journal of Thermophysics. 6 Nov 2019, 40 (11): 102. Bibcode:2019IJT....40..102B. doi:10.1007/s10765-019-2570-9 .
^ Clark, James H.; Hunt, Andrew J.; Raverty, Warwick; Duncan, Tony; Farmer, Thomas J.; McElroy, C. Rob; Moity, Laurianne; Constantinou, Andri; Bruyn, Mario De. Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents. Chemical Communications. 2014-07-29, 50 (68): 9650–9652. ISSN 1364-548X. PMID 25007289. doi:10.1039/C4CC04133J.
^ Sherwood, James; De bruyn, Mario; Constantinou, Andri; Moity, Laurianne; McElroy, C. Rob; Farmer, Thomas J.; Duncan, Tony; Raverty, Warwick; Hunt, Andrew J. (2014-09-04). "Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents". Chem. Commun. 50 (68): 9650–9652. doi:10.1039/c4cc04133j. PMID 25007289.
^ Watson, Allan J. B.; Jamieson, Craig; Greatrex, Ben; Murray, Jane; Kennedy, Alan R.; Wilson, Kirsty L. Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation. Beilstein Journal of Organic Chemistry. 2016-09-08, 12 (1): 2005–2011. ISSN 1860-5397. PMC 5082449 . PMID 27829904. doi:10.3762/bjoc.12.187.
^ Watson, Allan J. B.; Jamieson, Craig; Murray, Jane; Wilson, Kirsty L. Cyrene as a Bio-Based Solvent for the Suzuki–Miyaura Cross-Coupling. Synlett. 2017-12-11, 29 (5): 650–654. ISSN 0936-5214. doi:10.1055/s-0036-1589143.
^ Camp, Jason E.; Bousfield, Thomas W.; Mapesa, Kopano; Mistry, Liam. Synthesis of ureas in the bio-alternative solvent Cyrene (PDF). Green Chemistry. 2017-05-08, 19 (9): 2123–2128 [2023-11-14]. ISSN 1463-9270. S2CID 99613099. doi:10.1039/C7GC00908A. （原始内容存档 (PDF)于2023-11-17）.

[Baird2019-1] 1.0 ^1.1 ^1.2 Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville. Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds. International Journal of Thermophysics. 6 Nov 2019, 40 (11): 102. Bibcode:2019IJT....40..102B. doi:10.1007/s10765-019-2570-9 .

[:1-2] Clark, James H.; Hunt, Andrew J.; Raverty, Warwick; Duncan, Tony; Farmer, Thomas J.; McElroy, C. Rob; Moity, Laurianne; Constantinou, Andri; Bruyn, Mario De. Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents. Chemical Communications. 2014-07-29, 50 (68): 9650–9652. ISSN 1364-548X. PMID 25007289. doi:10.1039/C4CC04133J.

[:2-3] Sherwood, James; De bruyn, Mario; Constantinou, Andri; Moity, Laurianne; McElroy, C. Rob; Farmer, Thomas J.; Duncan, Tony; Raverty, Warwick; Hunt, Andrew J. (2014-09-04). "Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents". Chem. Commun. 50 (68): 9650–9652. doi:10.1039/c4cc04133j. PMID 25007289.

[4] Watson, Allan J. B.; Jamieson, Craig; Greatrex, Ben; Murray, Jane; Kennedy, Alan R.; Wilson, Kirsty L. Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation. Beilstein Journal of Organic Chemistry. 2016-09-08, 12 (1): 2005–2011. ISSN 1860-5397. PMC 5082449 . PMID 27829904. doi:10.3762/bjoc.12.187.

[5] Watson, Allan J. B.; Jamieson, Craig; Murray, Jane; Wilson, Kirsty L. Cyrene as a Bio-Based Solvent for the Suzuki–Miyaura Cross-Coupling. Synlett. 2017-12-11, 29 (5): 650–654. ISSN 0936-5214. doi:10.1055/s-0036-1589143.

[6] Camp, Jason E.; Bousfield, Thomas W.; Mapesa, Kopano; Mistry, Liam. Synthesis of ureas in the bio-alternative solvent Cyrene (PDF). Green Chemistry. 2017-05-08, 19 (9): 2123–2128 [2023-11-14]. ISSN 1463-9270. S2CID 99613099. doi:10.1039/C7GC00908A. （原始内容存档 (PDF)于2023-11-17）.

[1]

[2]

[3]

[4]

[5]

[6]