253340
3-Quinuclidinol
99%
Synonym(s):
1-Azabicyclo[2.2.2]octan-3-ol, 3-Hydroxyquinuclidine
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About This Item
Empirical Formula (Hill Notation):
C7H13NO
CAS Number:
Molecular Weight:
127.18
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
216-578-4
Beilstein/REAXYS Number:
80122
MDL number:
Assay:
99%
InChI key
IVLICPVPXWEGCA-UHFFFAOYSA-N
InChI
1S/C7H13NO/c9-7-5-8-3-1-6(7)2-4-8/h6-7,9H,1-5H2
SMILES string
OC1CN2CC[C@H]1CC2
assay
99%
Quality Level
functional group
hydroxyl
Related Categories
General description
(R)-3-Quinuclidinol is a valuable compound for the production of various pharmaceuticals.
Application
3-Quinuclidinol has been used:
- as chiral building block for many antimuscarinic agents
- in chemoselective α−iodination of various simple and multi-functionalised acrylic esters via Morita-Baylis-Hillman protocol
- as reagent for cleavage of β-keto and vinylogous β-keto esters
- as synthon for the preparation of cholinergic receptor ligands and anesthetics
- as catalyst for condensation of methyl vinyl ketone with aldehydes
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Regulatory Information
监管及禁止进口产品
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Khim.-Farm. Zh., 26, 12-12 (1992)
Tetrahedron Letters, 31, 4509-4509 (1990)
V I Cohen et al.
Journal of medicinal chemistry, 34(10), 2989-2993 (1991-10-01)
Seven analogues of 3-quinuclidinyl benzilate (QNB) in which one phenyl ring was replaced by an alkoxyalkyl moiety were synthesized and their affinities for the muscarinic cholinergic receptor determined. An oxygen in the beta-position of the moiety was not well-tolerated. By
Wen-Xia Zhang et al.
Organic letters, 15(19), 4917-4919 (2013-09-21)
A new keto reductase (ArQR), identified from Agrobacterium radiobacter ECU2556, can efficiently reduce 3-quinuclidinone in excellent enantioselectivity and high space-time yield for the synthesis of (R)-3-quinuclidinol, a chiral building block of many antimuscarinic agents. This is the first time that
Selective Cleavage of ?-Keto and Vinylogous ?-Keto Esters by 3-Quinuclidinol.
Parish EJ, et al.
Synthetic Communications, 5(5), 341-345 (1975)
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