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词条 Quinuclidine
释义

  1. References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464379026
| Reference =[1]
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Quinuclidine.svg
| ImageSizeL1 = 200px
| ImageNameL1 = Skeletal formula of quinuclidine
| ImageFileR1 = Quinuclidine 3D.png
| ImageSizeR1 = 200px
| ImageNameR1 = Ball-and-stick model of quinuclidine
| PIN = 1-Azabicyclo[2.2.2]octane[2]
| OtherNames = Quinuclidine[2]
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7246
| InChI = 1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
| InChIKey = SBYHFKPVCBCYGV-UHFFFAOYAA
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1209648
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SBYHFKPVCBCYGV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 100-76-5
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = XFX99FC5VI
| PubChem = 7527
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 38420
| SMILES = N12CCC(CC1)CC2
}}
|Section2={{Chembox Properties
| C=7
| H=13
| N=1
| Appearance =
| Density = 0.97 g/cm3
| MeltingPtC = 157 to 160
| MeltingPt_notes =
| BoilingPtC = 149.5
| BoilingPt_notes = at 760 mmHg
| Solubility =
| pKa = 11.0 (conjugate acid)
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 36.5
| AutoignitionPtC =
}}

Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 11.0.[3] This is due to greater availability of the nitrogen lone pair.{{Citation needed|date=February 2007}} It can be prepared by reduction of quinuclidone.

The compound is structurally related to DABCO, in which the other bridgehead is also nitrogen, and to tropane, which has a slightly different carbon frame.

Quinuclidine is found as a structural component of some biomolecules including quinine.

References

1. ^Quinuclidine {{webarchive |url=https://web.archive.org/web/20071015200029/http://www.sigmaaldrich.com/catalog/search/ProductDetail?ProdNo=22709&Brand=FLUKA |date=October 15, 2007 }} at Sigma-Aldrich
2. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | 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).}}
3. ^{{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}}

1 : Quinuclidines

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