Просмотр кода страницы Английская Википедия:1,5-Diazabicyclo(4.3.0)non-5-ene

{{Английская Википедия/Панель перехода}}
{{correct title|reason=bracket|1,5-Diazabicyclo[4.3.0]non-5-ene}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477186772
| Name = 1,5-Diazabicyclo[4.3.0]non-5-ene
| ImageFile = Structural formula of DBN.svg
| ImageSize = 200px
| ImageFile1 = DBN-3D-balls.png
| ImageAlt1 = DBN molecule
| ImageName = 1,5-Diazabicyclo(4.3.0)non-5-ene
| PIN = 2,3,4,6,7,8-Hexahydropyrrolo[1,2-''a'']pyrimidine
| OtherNames = DBN
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 68826
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SGUVLZREKBPKCE-UHFFFAOYSA-N 
| InChI = 1/C9H12N2/c10-11-8-4-2-6-9(11)5-1-3-7(8)9/h1-6H2
| InChIKey = HHCBYVLNFWNEJX-UHFFFAOYAD
| InChI1 = 1S/C9H12N2/c10-11-8-4-2-6-9(11)5-1-3-7(8)9/h1-6H2
| InChIKey1 = HHCBYVLNFWNEJX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 3001-72-7
| PubChem = 76349
| UNII = 978M4OL12Q
| EINECS = 221-087-3
| SMILES = C1CC2=NCCCN2C1
}}
|Section2={{Chembox Properties
| Formula = C{{sub|7}}H{{sub|12}}N{{sub|2}}
| MolarMass = 124.18 g/mol
| Density = 1.005 g/cm{{sup|3}}
| MeltingPt =
| BoilingPtC = 95 to 98
| BoilingPt_notes = at 7.5 mmHg
  }}
}}

'''1,5-Diazabicyclo[4.3.0]non-5-ene''' (DBN) is a [[chemical compound]] with the formula C{{sub|7}}H{{sub|12}}N{{sub|2}}.<ref>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}}</ref>  It is an [[amidine]] base used in [[organic synthesis]].  A related compound with related functions is [[DBU (chemistry)|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:<ref name="Article1">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. {{doi|10.1002/anie.196700761}}</ref>
:[[File:Synthesis-of-DBN.svg|frameless|alt=Synthesis of DBN|600px]]

The synthetic procedure starts with a [[Michael addition]] of [[2-Pyrrolidone|2-pyrrolidone]] to [[acrylonitrile]], followed by [[hydrogenation]], and finally [[Dehydration reaction|dehydration]].

==Uses==
===As a base in organic synthesis===
Similar to many other organic bases, DBN could be employed for [[dehydrohalogenation|dehydrohalogenation reactions]], base-catalyzed [[rearrangement reactions]], as well as [[Aldol condensation]].<ref>Oediger, H., Möller, F., & Eiter, K. "Bicyclic Amidines as Reagents in Organic Syntheses" ''Synthesis'', '''1972''', ''11'', 591–598. {{doi|10.1055/s-1972-21943}} </ref> Several examples are shown below:
* Elimination:<ref name="Article1" />
:[[File:Elimination-by-DBN.svg|frameless|An example of elimination reaction using DBN as the base|450px]]

*Epimerization of [[penicillin]] derivatives, catalyzed by DBN:<ref>Jackson, J.R. and Stoodley, R.J. "Equilibration of penicillanic acid derivatives" ''J. Chem. Soc. D'', '''1971''', 647-648</ref>
:[[File:Rearrangement-by-DBN.svg|800px|frameless]]

* Aldol condensation:<ref>Corey, E.J., Andersen, N.H., Carlson, R.M. "Total synthesis of prostaglandins. Synthesis of the pure ''dl''-E<sub>1</sub>, -F<sub>1α</sub>, -F<sub>1β</sub>, -A<sub>1</sub>, and -B<sub>1</sub> hormones" ''J. Am. Chem. Soc.'', '''1968''', ''90'', 12, 3245–3247 {{doi|10.1021/ja01014a053}}</ref>
:[[File:Aldol-condensation-by-DBN.svg|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 [[Rayon|processing cellulose fibers]] by acting as a replacement for the unstable [[N-Methylmorpholine N-oxide]] used for making [[lyocell]].<ref> 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}}</ref><ref>[https://ioncell.fi/ Ioncell - Enter the new era of textile production!]</ref>

==References==
<references/>

{{DEFAULTSORT:Diazabicyclo(4.3.0)non-5-ene, 1, 5-}}
[[Category:Amidines]]
[[Category:Non-nucleophilic bases]]
[[Category:Pyrrolopyrimidines]]
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