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维基百科

7-甲基-1,5,7-三氮杂双环［4.4.0］癸-5-烯

十月 08, 2023

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  
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]
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。

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.

十月 08, 2023
甲基, 三氮杂双环, 甲基, 三氮杂双环, mtbd, 是一种桥环胍基强碱, 在乙腈中pka, 在四氢呋喃中pka, 甲基, 三氮杂双环, iupac名1, methyl, hexahydropyrimido, pyrimidine别名, mtbd, methyl, methyl, triazabicyclo, hexahydro, methyl, pyrimido, pyrimidine识别cas号, 84030, pubchem, 123583chemspider, 110177smiles, cn1cccn2. 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 PubChem 123583ChemSpider 110177SMILES CN1CCCN2C1 NCCC2InChI InChI 1S C8H15N3 c1 10 5 3 7 11 6 2 4 9 8 10 11 h2 7H2 1H3InChIKey OEBXWWBYZJNKRK UHFFFAOYSA NEINECS 281 791 1性质化学式 C8H15N3摩尔质量 153 225 g mol g mol 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nD 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 H314P 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 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 Hyvari Paulus Alopaeus Ville Kilpelainen 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 c 1994 2019 ACD Labs Retrieved from SciFinder 2019 08 14 Ishikawa T Superbases for Organic Synthesis Guanidines Amidines Phosphazenes and Related Organocatalysts John Wiley amp 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 Kilpelainen 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 取自 https zh wikipedia org w index php title 7 甲基 1 5 7 三氮杂双环 4 4 0 癸 5 烯 amp oldid 61932675, 维基百科，wiki，书籍，书籍，图书馆，

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