维基百科

7-甲基-1,5,7-三氮杂双环［4.4.0］癸-5-烯

化合物

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]

7-甲基-1,5,7-三氮杂双环[4.4.0]癸-5-烯[1]
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  checkY
PubChem 123583
ChemSpider 110177
SMILES
 
  • CN1CCCN2C1=NCCC2
InChI
 
  • InChI=1S/C8H15N3/c1-10-5-3-7-11-6-2-4-9-8(10)11/h2-7H2,1H3
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]
热导率 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
《全球化学品统一分类和标签制度》（简称“GHS”）中腐蚀性物质的标签图案
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。

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
  1. ^ （[//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. ^ 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. 
  3. ^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-08-14]
  4. ^ Ishikawa, T. Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts. John Wiley & Sons. 2009. ISBN 9780470740866. 
  5. ^ 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. 
  6. ^ Thomas R. Welter. Process for the preparation of alkylated polycyclic guanidines by N-alkylation of polycyclic guanidines with dialkylcarbonate, 2013. WO 2013055747 A1.
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ 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. 
  11. ^ 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.
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