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Revision as of 12:24, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 455753553 of page Quinuclidine for the Chem/Drugbox validation project (updated: '').  Latest revision as of 12:36, 17 September 2024 edit DielsAlderMenace (talk | contribs)9 editsm SpellingTag: Visual edit 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 412526553 | verifiedrevid = 464379026
| Reference=<ref> at ]</ref> | Reference =<ref> {{webarchive |url=https://web.archive.org/web/20071015200029/http://www.sigmaaldrich.com/catalog/search/ProductDetail?ProdNo=22709&Brand=FLUKA |date=October 15, 2007 }} at ]</ref>
| ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Quinuclidine.svg | ImageFileL1 = Quinuclidine.svg
| ImageSizeL1 = 150px | ImageSizeL1 = 140px
| ImageNameL1 = Skeletal formula of quinuclidine | ImageNameL1 = Skeletal formula of quinuclidine
| ImageFileR1 = Quinuclidine 3D.png | ImageFileR1 = Quinuclidine 3D.png
| ImageSizeR1 = 150px | ImageSizeR1 = 140px
| ImageNameR1 = Ball-and-stick model of quinuclidine | ImageNameR1 = Ball-and-stick model of quinuclidine
| PIN = 1-Azabicyclooctane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 169 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The name quinuclidine is retained for general nomenclature only (see Table 2.6).}}</ref>
| IUPACName = 1-Azabicyclooctane
| OtherNames = | OtherNames = Quinuclidine<ref name=iupac2013 />
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 100-76-5
| Beilstein = 103111
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 38420
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 1209648
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7246 | ChemSpiderID = 7246
| EC_number = 202-887-1
| Gmelin = 26726
⚫ | PubChem = 7527
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = XFX99FC5VI
| InChI = 1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 | InChI = 1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
| InChIKey = SBYHFKPVCBCYGV-UHFFFAOYAA | InChIKey = SBYHFKPVCBCYGV-UHFFFAOYAA
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 1209648
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 | StdInChI = 1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SBYHFKPVCBCYGV-UHFFFAOYSA-N | StdInChIKey = SBYHFKPVCBCYGV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 100-76-5
⚫ | PubChem = 7527
⚫ | ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ | ChEBI = 38420
| SMILES = N12CCC(CC1)CC2 | SMILES = N12CCC(CC1)CC2
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=7
| Formula = C<sub>7</sub>H<sub>13</sub>N<sub></sub>
| H=13
| MolarMass = 111.18 g/mol
| Appearance = | N=1
| Appearance =
| Density = | Density = 0.97 g/cm<sup>3</sup>
| MeltingPtC = 157 to 160
| MeltingPt = 157–160&nbsp;°C
| BoilingPt = | MeltingPt_notes =
| Solubility = | BoilingPtC = 149.5
| BoilingPt_notes = at 760 mmHg
⚫ | pKa = 11.0 (conjugate acid)
| Solubility =
⚫ }}
⚫ | pKa = 11.0 (conjugate acid)
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
| FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=Quinuclidine |url=https://pubchem.ncbi.nlm.nih.gov/compound/7527#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|310|315|318}}
| PPhrases = {{P-phrases|262|264|264+265|270|280|301+316|302+352|305+354+338|316|317|321|330|332+317|361+364|362+364|405|501}}
⚫ | MainHazards =
| FlashPtC = 36.5
| AutoignitionPtC =
⚫ }}
}} }}

'''Quinuclidine''' is an ] with the formula {{chem2|HC(C2H4)3N}}. It is a ] ] that can be viewed as a tied back version of ]. It is a colorless solid. It is used as a reagent (base) and catalyst. It can be prepared by reduction of ] and has great utility in ] When protonated, Quinuclidine's heterocyclic structure allows its amine group to serve as a strong electrophile in the Cormas-Grisius Electrophilic Benzene Addition.

==Structure and chemical properties==
Regarding its structure, quinuclidine is unusual in that the methylene hydrogen atoms are eclipsed within each of the three ethylene linkages. Furthermore, the cyclohexane rings, of which there are three, adopt the ]s, not the usual chair conformations.<ref>{{cite journal |doi=10.1021/jo00384a013 |title=Charge-Rransfer Interactions of Amines with Tetrahalomethanes. X-Ray Crystal Structures of the Donor-Acceptor Complexes of Quinuclidine and Diazabicyclo &#91;2.2.2&#93;Octane with Carbon Tetrabromide |year=1987 |last1=Blackstock |first1=S. C. |last2=Lorand |first2=J. P. |last3=Kochi |first3=J. K. |journal=The Journal of Organic Chemistry |volume=52 |issue=8 |pages=1451–1460 }}</ref>

Quinuclidine is a relatively strong organic ] with ] of the ] of 11.3.<ref>{{cite journal |title=Azatriquinanes: Synthesis, Structure, and Reactivity |author1=Hext, N. M. |author2=Hansen, J. |author3=Blake, A. J. |author4=Hibbs, D. E. |author5=Hursthouse, M. B. |author6=Shishkin, O. V. |author7=Mascal, M. |journal=J. Org. Chem. |year=1998 |volume=63 |issue=17 |pages=6016–6020 |doi=10.1021/jo980788s |pmid=11672206}}</ref> The basicity of other quinuclidines have been evaluated:
3-hydroxy- quinuclidine (9.9), ] (9.3), 3-chloroquinuclidine (8.9), ] (8.7), and ] (7.2).<ref>{{cite journal |doi=10.1021/jo026671s |title=Correlation between p''Ka'' and Reactivity of Quinuclidine-Based Catalysts in the Baylis−Hillman Reaction: Discovery of Quinuclidine as Optimum Catalyst Leading to Substantial Enhancement of Scope |year=2003 |last1=Aggarwal |first1=Varinder K. |last2=Emme |first2=Ingo |last3=Fulford |first3=Sarah Y. |journal=The Journal of Organic Chemistry |volume=68 |issue=3 |pages=692–700 |pmid=12558387 }}</ref>

It forms adducts with a variety of ]s. Because of its compact structure, quinuclidine binds to ] more tightly than does triethylamine.<ref name=JHC>{{cite journal| doi=10.1002/jhet.5570430601 | title=Chemistry of quinuclidines as nitrogen bicyclic bridged-ring structures | year=2006 | last1=Hamama | first1=Wafaa S. | last2=El-Magid | first2=Osama. M. Abd | last3=Zoorob | first3=Hanafi H. | journal=Journal of Heterocyclic Chemistry | volume=43 | issue=6 | pages=1397–1420 | doi-access=free }}</ref>

==Derivatives and analogues==
:] is a quinuclidine derivative.]]
Quinuclidine is structurally related to ], in which the other bridgehead is also nitrogen, and to ], which has a slightly different carbon frame. ] alkaloids, e.g. ], feature quinuclidine substituents.<ref name=JHC/> ], a simple quinuclidine derivative, is a drug used for treatment of ].

==References==
<references/>

]
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