1,5,7-三氮杂双环[4.4.0]癸-5-烯

化合物

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

1,5,7-三氮杂双环[4.4.0]癸-5-烯[1]
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  checkY[2]
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[3] (共轭酸水中的pKa ); 26.03[4] (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。

反应

编辑

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]

 
己内酯英语Caprolactone的开环聚合反应 。TBD是己内酯以及聚己内酯开环聚合英语ring opening polymerization的催化剂。TBD是两性催化剂英语bifunctional catalyst酰基以及氢键反应同时间内发生。[7][8]
 
碳负离子的去质子化反应。TBD可用来研究碳负离子去质子化以及酚与CH酸形成多重氢键的反应。[9]

参见

编辑

参考文献

编辑
  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). 
  2. ^ 5807-14-7 CAS Manufactory. ChemicalBook---Chemical Search Engine. [2019-08-29]. (原始内容存档于2019-08-29). 
  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. 
  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 pKa Units:  Unification of Different Basicity Scales. J. Org. Chem. 2005, 70: 1019–1028. PMID 15675863. doi:10.1021/jo048252w. 
  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 ( 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 ; 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.