二氫左旋葡萄糖酮
外觀
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二氫左旋葡萄糖酮 | |
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IUPAC名 (1R,5S)-7,8-Dioxabicyclo[3.2.1]octan-2-one | |
別名 | Cyrene |
識別 | |
CAS號 | 53716-82-8 |
PubChem | 16762483 |
ChemSpider | 9150700 |
SMILES |
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EINECS | 807-130-4 |
性質 | |
化學式 | C6H8O3 |
摩爾質量 | 128.13 g·mol−1 |
外觀 | 澄清或黃色液體 |
密度 | 1.2508 g/cm3 (20 °C) [1] |
沸點 | 226 °C(499 K) |
溶解性(水) | miscible |
蒸氣壓 | 14.4 Pa (25 °C) [1] |
折光度n D |
1.4732 (20 °C) [1] |
危險性 | |
GHS危險性符號![]() | |
GHS提示詞 | 警告 |
H-術語 | H319 |
P-術語 | P305+351+338, P313 |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
二氫左旋葡萄糖酮是一種有機化合物,化學式為C6H8O3。它是可生物降解的非質子偶極溶劑,是二甲基甲酰胺(DMF)和N-甲基吡咯烷酮(NMP)的環保替代品。[2]
它可以用作一些有機反應中的溶劑,用來替代DMF,如門秀金反應、[3]薗頭耦合反應、[4]鈴木反應[5]以及尿素的合成[6]。
參考文獻
[編輯]- ^ 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. (原始內容存檔 (PDF)於2023-11-17).