二氢左旋葡萄糖酮

化合物

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]

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) [1]
沸点 226 °C(499 K)
溶解性 miscible
蒸气压 14.4 Pa (25 °C) [1]
折光度n
D
1.4732 (20 °C) [1]
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》(简称“GHS”)中有害物质的标签图案
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。

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]薗头耦合反应[4]铃木反应[5]以及尿素的合成[6]

参考文献

编辑
  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. (原始内容存档 (PDF)于2023-11-17).