7-甲基-1,5,7-三氮杂双环[4.4.0]癸-5-烯
外观
7-甲基-1,5,7-三氮杂双环[4.4.0]癸-5-烯[1] | |
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IUPAC名 1-Methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine | |
别名 | mTBD; 7-Methyl-TBD; 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene; 1,3,4,6,7,8-Hexahydro-1-methyl-2H-pyrimido[1,2-a]pyrimidine |
识别 | |
CAS号 | 84030-20-6 ![]() |
PubChem | 123583 |
ChemSpider | 110177 |
SMILES |
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InChI |
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InChIKey | OEBXWWBYZJNKRK-UHFFFAOYSA-N |
EINECS | 281-791-1 |
性质 | |
化学式 | C8H15N3 |
摩尔质量 | 153.225 g/mol g·mol⁻¹ |
外观 | 澄清液体[2] |
密度 | 1.063 g/cm3[2] 1.18±0.1 g/cm3(20 °C)[3] |
熔点 | 17 °C(290 K)[2] |
沸点 | 263 °C(536 K)[2] |
熱導率 | 0.144 W/m/K[2] |
折光度n D |
1.5357[2] |
黏度 | 7.1 cP[2] |
危险性 | |
GHS危险性符号![]() | |
GHS提示词 | 危险 |
H-术语 | H314 |
P-术语 | P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P405, P501 |
热力学 | |
热容 | 1.75 J/g/K[2] |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
7-甲基-1,5,7-三氮杂双环[4.4.0]癸-5-烯(mTBD)是一种桥环胍基强碱,在乙腈中pKa = 25.43,在四氢呋喃中pKa = 17.9。[4]
制备
[编辑]标题化合物可由1,5,7-三氮杂双环[4.4.0]癸-5-烯的锂盐和氯甲烷反应得到[5];或以碳酸二甲酯为甲基化试剂进行制备[6]。
性质及用途
[编辑]7-甲基-1,5,7-三氮杂双环[4.4.0]癸-5-烯可以和一些金属化合物(如碘化亚铜等)反应,生成相应的配位化合物。[7]
它和其它1,5,7-三氮杂双环[4.4.0]癸-5-烯及胍类超碱一样,可以被用作一些化学反应的催化剂。[8]它可以和二氧化碳反应,可用于碳捕集与封存。[9]
它可以和一些酸反应,生成离子液体,并可用于纤维素的溶解。[10][11]
参考文献
[编辑]- ^ ([//web.archive.org/web/20190808190624/https://pubchem.ncbi.nlm.nih.gov/compound/123583 页面存档备份,存于互联网档案馆) 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene]. PubChem. [2019-08-14]
- ^ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 Baird, Zachariah Steven; Dahlberg, Artur; Uusi-Kyyny, Petri; Osmanbegovic, Nahla; Witos, Joanna; Helminen, Jussi; Cederkrantz, Daniel; Hyväri, Paulus; Alopaeus, Ville; Kilpeläinen, Ilkka; Wiedmer, Susanne K.; Sixta, Herbert. Physical properties of 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (mTBD). International Journal of Thermophysics. 2019, 40 (71). doi:10.1007/s10765-019-2540-2.
- ^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-08-14]
- ^ Ishikawa, T. Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts. John Wiley & Sons. 2009. ISBN 9780470740866.
- ^ Zhu, Jieping. 1,5,7-Triazabicyclo[4.4.0]dec-5-ene, Polymer-supported (PTBD). e-EROS Encyclopedia of Reagents for Organic Synthesis. 2003. doi:10.1002/047084289X.rn00330.
- ^ Thomas R. Welter. Process for the preparation of alkylated polycyclic guanidines by N-alkylation of polycyclic guanidines with dialkylcarbonate, 2013. WO 2013055747 A1.
- ^ Oakley, Sarah H.; Coles, Martyn P.; Hitchcock, Peter B. Structural Consequences of the Prohibition of Hydrogen Bonding in Copper−Guanidine Systems. Inorganic Chemistry. 2004, 43 (16): 5168–5172. ISSN 0020-1669. doi:10.1021/ic0495970.
- ^ Simoni, D.; Rondanin, R.; Morini, M.; Baruchello, R.; Invidiata, F. P. 1,5,7- Triazabicyclo[4.4.0]Dec-1-Ene (TBD), 7-Methyl-TBD (MTBD) and the PolymerSupported TBD (P-TBD): Three Efficient Catalysts for the Nitroaldol (Henry) Reaction and for the Addition of Dialkyl Phosphites to Unsaturated Systems. Tetrahedron Lett. 2000, 41 (10): 1607–1610. doi:10.1016/S0040-4039(99)02340-0.
- ^ Yang, Z.-Z.; Zhao, Y.-N.; He, L.-N. CO2 Chemistry: Task-Specific Ionic Liquids for CO2 Capture/ Activation and Subsequent Conversion. RSC Adv. 2011, 1 (4): 545– 567. doi:10.1039/C1RA00307K.
- ^ Parviainen, A.; King, A. W. T.; Mutikainen, I.; Hummel, M.; Selg, C.; Hauru, L. K. J.; Sixta, H.; Kilpeläinen, I. Predicting Cellulose Solvating Capabilities of Acid–Base Conjugate Ionic Liquids. ChemSusChem. 2013, 6 (11): 2161–2169. doi:10.1002/cssc.201300143.
- ^ Sixta, Herbert; Hummel, Michael; Le Boulch, Kadvael; Kilpelainen A., Ilkka; King, Alistair W. T.; Helminen K. J., Jussi; Hellsten, Sanna. A process for making a cellulose fiber or film using ionic liquids, 2018. WO 2018138416.