1,5,7-三氮杂双环[4.4.0]癸-5-烯

1,5,7-三氮杂双环［4.4.0］癸-5-烯
	IUPAC名; 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine
别名	TBD
识别
CAS号	5807-14-7
PubChem	79873
ChemSpider	72164
SMILES	N\2=C1/NCCCN1CCC/2;
InChI	1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9);
InChIKey	FVKFHMNJTHKMRX-UHFFFAOYAP
性质
化学式	C7H13N3
摩尔质量	139.2 g·mol−1
熔点	125—130 °C（257—266 °F；398—403 K）
pKa	15.2 ± 1.0 （共轭酸水中的pKa ); 26.03 （共轭酸乙腈中的pKa )
危险性
警示术语	R：R34
安全术语	S：S26 S36/37/39 S45
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD）是一种桥环胍基强碱，在乙腈中pK_a = 25.98，在四氢呋喃中pK_a = 21.00。^[5]

反应

TBD是一种有机可溶碱，可以被用作一些化学反应的催化剂。这些反应包括了：^[5]^[6]

参见

7-甲基-1,5,7-三氮杂双环［4.4.0］癸-5-烯

参考文献

^ 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 345571. Sigma-Aldrich. [2019-08-29]. （原始内容存档于2016-02-02）.
^ 5807-14-7 CAS Manufactory. ChemicalBook---Chemical Search Engine. [2019-08-29]. （原始内容存档于2019-08-29）.
^ Kaupmees, K.; Trummal, A.; Leito, I. Basicities of Strong Bases in Water: A Computational Study. Croat. Chem. Acta. 2014, 87: 385–395. doi:10.5562/cca2472.
^ Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pK_a Units: Unification of Different Basicity Scales. J. Org. Chem. 2005, 70: 1019–1028. PMID 15675863. doi:10.1021/jo048252w.
^ ^5.0 ^5.1 Huczynski, Adam; Brzezinski, Bogumil, 1,5,7-Triazabicyclo[4.4.0]dec-5-ene, Chichester, UK: John Wiley & Sons, Ltd, 2008-03-14, ISBN 0-471-93623-5, doi:10.1002/047084289x.rn00786
^ Sabot, Cyrille; Kumar, Kanduluru Ananda; Meunier, Stéphane; Mioskowski, Charles. A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions. Tetrahedron Lett. 2007: 3863–3866. doi:10.1016/j.tetlet.2007.03.146.
^ Pratt, Russell C.; Lohmeijer, Bas G. G.; Long, David A.; Waymouth, Robert M.; Hedrick, James L. Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters. 美国化学会志. 2006, 128 (14): 4556–4557. doi:10.1021/ja060662+.
^ Reaction specs: 自由基引发剂 4-pyrenebutanol (芘 enables end-group（英语：end-group） determination by 紫外-可见分光光度法) and 单体 caprolactone（英语：caprolactone） added in ratio 1:100, targeted 聚合度 = 100, with TBD cat. 0.5% in 苯; 72% conversion in 8 hours; polydispersity index（英语：polydispersity index） 1.16
^ Huczyński, A.; Binkowska, I.; Jarczewski, A.; Brzezinski, B. Spectroscopic studies of the 1:1 complexes of 4-nitrophenyl(bis(ethylsulfonyl))methane and phenyl(bis(ethylsulfonyl))methane with 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene and 1,5,7-triazabicyclo(4.4.0)dec-5-ene. J. Mol. Struc. 2007, 841 (1–3): 133–136. doi:10.1016/j.molstruc.2007.01.005.

[Sigma-Aldrich-1] 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 345571. Sigma-Aldrich. [2019-08-29]. （原始内容存档于2016-02-02）.

[ChemicalBook---Chemical_Search_Engine-2] 5807-14-7 CAS Manufactory. ChemicalBook---Chemical Search Engine. [2019-08-29]. （原始内容存档于2019-08-29）.

[Kaupmees_CCA-3] Kaupmees, K.; Trummal, A.; Leito, I. Basicities of Strong Bases in Water: A Computational Study. Croat. Chem. Acta. 2014, 87: 385–395. doi:10.5562/cca2472.

[Kaljurand_2005_JOC-4] Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pK_a Units: Unification of Different Basicity Scales. J. Org. Chem. 2005, 70: 1019–1028. PMID 15675863. doi:10.1021/jo048252w.

[Huczynski_Brzezinski_p.-5] 5.0 ^5.1 Huczynski, Adam; Brzezinski, Bogumil, 1,5,7-Triazabicyclo[4.4.0]dec-5-ene, Chichester, UK: John Wiley & Sons, Ltd, 2008-03-14, ISBN 0-471-93623-5, doi:10.1002/047084289x.rn00786

[6] Sabot, Cyrille; Kumar, Kanduluru Ananda; Meunier, Stéphane; Mioskowski, Charles. A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions. Tetrahedron Lett. 2007: 3863–3866. doi:10.1016/j.tetlet.2007.03.146.

[7] Pratt, Russell C.; Lohmeijer, Bas G. G.; Long, David A.; Waymouth, Robert M.; Hedrick, James L. Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters. 美国化学会志. 2006, 128 (14): 4556–4557. doi:10.1021/ja060662+.

[8] Reaction specs: 自由基引发剂 4-pyrenebutanol (芘 enables end-group（英语：end-group） determination by 紫外-可见分光光度法) and 单体 caprolactone（英语：caprolactone） added in ratio 1:100, targeted 聚合度 = 100, with TBD cat. 0.5% in 苯; 72% conversion in 8 hours; polydispersity index（英语：polydispersity index） 1.16

[9] Huczyński, A.; Binkowska, I.; Jarczewski, A.; Brzezinski, B. Spectroscopic studies of the 1:1 complexes of 4-nitrophenyl(bis(ethylsulfonyl))methane and phenyl(bis(ethylsulfonyl))methane with 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene and 1,5,7-triazabicyclo(4.4.0)dec-5-ene. J. Mol. Struc. 2007, 841 (1–3): 133–136. doi:10.1016/j.molstruc.2007.01.005.

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