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253340

Sigma-Aldrich

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:
1619-34-7
Molecular Weight:
127.18
Beilstein:
80122
EC Number:
216-578-4
MDL number:
MFCD00151326
UNSPSC Code:
12352100
PubChem Substance ID:
24855306
NACRES:
NA.22

Quality Level

100

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

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

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

Certificates of Analysis (COA)

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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)
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
Khim.-Farm. Zh., 26, 12-12 (1992)
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