1,5-Diazabicyclo(4.3.0)non-5-ene

bracket 1,5-Diazabicyclo[4.3.0]non-5-ene changed changed 477186772 1,5-Diazabicyclo[4.3.0]non-5-ene Structural formula of DBN.svg 200px DBN-3D-balls.png DBN molecule 1,5-Diazabicyclo(4.3.0)non-5-ene 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine DBN changed chemspider 68826 changed chemspider 1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2 changed chemspider SGUVLZREKBPKCE-UHFFFAOYSA-N 1/C9H12N2/c10-11-8-4-2-6-9(11)5-1-3-7(8)9/h1-6H2 HHCBYVLNFWNEJX-UHFFFAOYAD 1S/C9H12N2/c10-11-8-4-2-6-9(11)5-1-3-7(8)9/h1-6H2 HHCBYVLNFWNEJX-UHFFFAOYSA-N correct CAS 3001-72-7 76349 978M4OL12Q 221-087-3 C1CC2=NCCCN2C1 7 12 2 colorless viscous liquid 1.005 g/cm3 95 to 98 at 7.5 mmHg 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is a chemical compound with the formula C7H12N2.Savoca, Ann. C. "1,5-Diazabicyclo[4.3.0]non-5-ene" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. 10.1002/047084289X.rd010.pub2 It is an amidine base used in organic synthesis. A related compound with related functions is 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The relatively complex nature of the formal names for DBU and DBN (hence the common use of acronyms) reflects the fact that these compounds are bicyclic and contain several functional groups. Synthesis DBN could be synthesized in the following manner, similarly to DBU:Möller, F.; Oediger, H. "1,5-Diazabicyclo[5.4.0]undec-5-ene, a New Hydrogen Halide Acceptor" Angew. Chem. Int. Ed. Engl. , 1967, 5, 76. 10.1002/anie.196700761 frameless|alt=Synthesis of DBN|600px The synthetic procedure starts with a Michael addition of 2-pyrrolidone to acrylonitrile, followed by hydrogenation, and finally dehydration. Uses As a base in organic synthesis Similar to many other organic bases, DBN could be employed for dehydrohalogenation reactions, base-catalyzed rearrangement reactions, as well as Aldol condensation.Oediger, H., Möller, F., & Eiter, K. "Bicyclic Amidines as Reagents in Organic Syntheses" Synthesis, 1972, 11, 591–598. 10.1055/s-1972-21943 Several examples are shown below: Elimination: frameless|An example of elimination reaction using DBN as the base|450px Epimerization of penicillin derivatives, catalyzed by DBN:Jackson, J.R. and Stoodley, R.J. "Equilibration of penicillanic acid derivatives" J. Chem. Soc. D, 1971, 647-648 800px|frameless Aldol condensation:Corey, E.J., Andersen, N.H., Carlson, R.M. "Total synthesis of prostaglandins. Synthesis of the pure dl-E1, -F1α, -F1β, -A1, and -B1 hormones" J. Am. Chem. Soc., 1968, 90, 12, 3245–3247 10.1021/ja01014a053 frameless|An example of aldol condensation|750px DBN salt as an ionic liquid The acetate salt of DBN is a room-temperature ionic liquid used for processing cellulose fibers by acting as a replacement for the unstable N-Methylmorpholine N-oxide used for making lyocell. Zhang, Jinming; Wu, Jin; Yu, Jian; Zhang, Xiaoyu; He, Jiasong; Zhang, Jun. "Application of ionic liquids for dissolving cellulose and fabricating cellulose-based materials: state of the art and future trends." Mat. Chem. Front. 2017, 1 (7), 1273-90. 10.1039/C6QM00348FIoncell - Enter the new era of textile production! References Category:Amidines Category:Non-nucleophilic bases Category:Pyrrolopyrimidines