二氫左旋葡萄糖酮

化合物

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,是二甲基甲醯胺(DMF)和N-甲基吡咯烷酮(NMP)的環保替代品。[2]

二氫左旋葡萄糖酮
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
 
  • [C@H]12CCC([C@H](OC1)O2)=O
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 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
《全球化學品統一分類和標籤制度》(簡稱「GHS」)中有害物質的標籤圖案
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。

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. ^ 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 . 
  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. 
  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. (原始內容存檔 (PDF)於2023-11-17).