253340
3-Quinuclidinol
99%
Synonym(s):
1-Azabicyclo[2.2.2]octan-3-ol, 3-Hydroxyquinuclidine
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About This Item
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Quality Level
Assay
99%
mp
220-223 °C (lit.)
SMILES string
OC1CN2CC[C@H]1CC2
InChI
1S/C7H13NO/c9-7-5-8-3-1-6(7)2-4-8/h6-7,9H,1-5H2
InChI key
IVLICPVPXWEGCA-UHFFFAOYSA-N
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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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Selective Cleavage of ?-Keto and Vinylogous ?-Keto Esters by 3-Quinuclidinol.
Synthetic Communications, 5(5), 341-345 (1975)
Synthesis and local anaesthetic activities of 3-(2-alkoxyphenylcarbamoyloxy)chinuclidinium chlorides.
Die Pharmazie, 48(6), 465-466 (1993-06-01)
Khim.-Farm. Zh., 26, 12-12 (1992)
Tetrahedron Letters, 31, 4509-4509 (1990)
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
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