The correct title of this article is 1,5-Diazabicyclo[4.3.0]non-5-ene. The substitution of any brackets is due to technical restrictions.
1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is a chemical compound with the formula C7H12N2.[1] 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.
^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. doi:10.1002/047084289X.rd010.pub2
^ abMöller, 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. doi:10.1002/anie.196700761
^Oediger, H., Möller, F., & Eiter, K. "Bicyclic Amidines as Reagents in Organic Syntheses" Synthesis, 1972, 11, 591–598. doi:10.1055/s-1972-21943
^Jackson, J.R. and Stoodley, R.J. "Equilibration of penicillanic acid derivatives" J. Chem. Soc. D, 1971, 647-648
^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 doi:10.1021/ja01014a053
^ 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. doi:10.1039/C6QM00348F
^Ioncell - Enter the new era of textile production!
March 21, 2023
diazabicyclo, correct, title, this, article, diazabicyclo, substitution, brackets, technical, restrictions, diazabicyclo, chemical, compound, with, formula, c7h12n2, amidine, base, used, organic, synthesis, related, compound, with, related, functions, diazabic. The correct title of this article is 1 5 Diazabicyclo 4 3 0 non 5 ene The substitution of any brackets is due to technical restrictions 1 5 Diazabicyclo 4 3 0 non 5 ene DBN is a chemical compound with the formula C7H12N2 1 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 1 5 Diazabicyclo 4 3 0 non 5 ene NamesPreferred IUPAC name 2 3 4 6 7 8 Hexahydropyrrolo 1 2 a pyrimidineOther names DBNIdentifiersCAS Number 3001 72 7 Y3D model JSmol Interactive imageChemSpider 68826 NECHA InfoCard 100 019 171EC Number 221 087 3PubChem CID 76349UNII 978M4OL12QCompTox Dashboard EPA DTXSID10184087InChI InChI 1S C7H12N2 c1 3 7 8 4 2 6 9 7 5 1 h1 6H2 NKey SGUVLZREKBPKCE UHFFFAOYSA N NInChI 1 C9H12N2 c10 11 8 4 2 6 9 11 5 1 3 7 8 9 h1 6H2Key HHCBYVLNFWNEJX UHFFFAOYADInChI 1S C9H12N2 c10 11 8 4 2 6 9 11 5 1 3 7 8 9 h1 6H2Key HHCBYVLNFWNEJX UHFFFAOYSA NSMILES C1CC2 NCCCN2C1PropertiesChemical formula C7H12N2Molar mass 124 18 g molDensity 1 005 g cm3Boiling point 95 to 98 C 203 to 208 F 368 to 371 K at 7 5 mmHgExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis 2 Uses 2 1 As a base in organic synthesis 2 2 DBN salt as an ionic liquid 3 ReferencesSynthesis EditDBN could be synthesized in the following manner similarly to DBU 2 The synthetic procedure starts with a Michael addition of 2 pyrrolidone to acrylonitrile followed by hydrogenation and finally dehydration Uses EditAs a base in organic synthesis Edit Similar to many other organic bases DBN could be employed for dehydrohalogenation reactions base catalyzed rearrangement reactions as well as Aldol condensation 3 Several examples are shown below Elimination 2 Epimerization of penicillin derivatives catalyzed by DBN 4 Aldol condensation 5 DBN salt as an ionic liquid Edit 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 6 7 References Edit 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 amp Sons New York doi 10 1002 047084289X rd010 pub2 a b Moller 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 doi 10 1002 anie 196700761 Oediger H Moller F amp Eiter K Bicyclic Amidines as Reagents in Organic Syntheses Synthesis 1972 11 591 598 doi 10 1055 s 1972 21943 Jackson J R and Stoodley R J Equilibration of penicillanic acid derivatives J Chem Soc D 1971 647 648 Corey E J Andersen N H Carlson R M Total synthesis of prostaglandins Synthesis of the pure dl E1 F1a F1b A1 and B1 hormones J Am Chem Soc 1968 90 12 3245 3247 doi 10 1021 ja01014a053 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 doi 10 1039 C6QM00348F Ioncell Enter the new era of textile production Retrieved from https en wikipedia org w index php title 1 5 Diazabicyclo 4 3 0 non 5 ene amp oldid 1122943985, wikipedia, wiki, book, books, library,
