34583-34-1

Basic information

• Product Name: (S)-(+)-3-Quinuclidinol
• Synonyms: (S)-(+)-3-QUINUCLIDINOL;S-(+)-3-HYDROXY QUINUCLIDINE;(S)-3-Quinuclidinol. Hydrochloride;(S)-(+)-3-Hydroxy quinuclidine ,98%;(S)-quinuclidin-3-ol;(3S)-Quinuclidin-3-ol;1-Azabicyclo[2.2.2]octan-3-ol, (3S)-;Solifenacin Succinate interMediate B
• CAS NO: 34583-34-1
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18422
• Mol File: 34583-34-1.mol
• Article Data: 34

Chemical Properties

• Melting Point: 215-217 °C
• Boiling Point: 206.9 °C at 760 mmHg
• Flash Point: 97.7 °C
• Appearance: /
• Density: 1.13 g/cm³
• Vapor Pressure: 0.0545mmHg at 25°C
• Refractive Index: 1.549
• PKA: 14.75±0.20(Predicted)
• CAS DataBase Reference: (S)-(+)-3-Quinuclidinol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-3-Quinuclidinol(34583-34-1)
• EPA Substance Registry System: (S)-(+)-3-Quinuclidinol(34583-34-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 34583-34-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white crystalline powder

InChI:InChI=1/C7H13NO/c9-7-5-8-3-1-6(7)2-4-8/h6-7,9H,1-5H2/t7-/m1/s1

Upstream product

• 65732-89-0 quinuclidin-3-yl butyrate b 
• 3731-38-2 3-Quinuclidinone 
• 1200405-02-2 (S)-quinuclidin-3-ol butyric acid salt 
• 109181-80-8 (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 109175-05-5 (3S,4S)-3-Hydroxy-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 109174-98-3 Methanesulfonic acid (2S,3S,6S)-3-dimethylcarbamoylmethyl-6-methoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester 
• 109175-01-1 (2S,4aR,8aS)-2-Methoxy-octahydro-pyrano[2,3-c]pyridine-7-carboxylic acid benzyl ester 
• 109175-02-2 (4aR,8aS)-4,4a,5,6,8,8a-Hexahydro-pyrano[2,3-c]pyridine-7-carboxylic acid benzyl ester 
• 109175-00-0 (2S,4aR,8aS)-2-Methoxy-hexahydro-pyrano[2,3-c]pyridin-6-one 
• 108943-51-7 (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 64889-23-2 Methyl 4-C-<(Dimethylcarboxamido)methyl>-2,3,4-trideoxy-α-D-erythrohex-2-enopyranoside 
• 109175-07-7 (S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-aza-bicyclo[2.2.2]octane 
• 34286-16-3 2-ethoxycarbonyl-3-quinuclidinone 
• 946513-99-1 4-nitrobenzoic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester fumarate 

Downstream Products

• 62869-68-5 (S)-3-(1-azabicyclo<2.2.2>octyl) α-hydroxy-α,α-diphenylacetate 
• 114121-68-5 (S)-2-[(S)-(1-Aza-bicyclo[2.2.2]oct-3-yl)oxy]-1-cyclopentyl-1-phenyl-ethanol 
• 114121-68-5 (R)-2-[(S)-(1-Aza-bicyclo[2.2.2]oct-3-yl)oxy]-1-cyclopentyl-1-phenyl-ethanol 
• 732228-02-3 (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester 
• 774517-20-3 (3S)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate 
• 65732-89-0 (R)-quinuclidin-3-yl butyrate 
• 123442-07-9 R(-)-3-phthalimidoquinuclidine 
• 1196093-11-4 1-phenyl-cycloheptanecarboxylic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester 
• 1401090-53-6 [(3S)-1-azabicyclo[2.2.2]octan-3-yl] N-[2-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]propan-2-yl]carbamate 
• 1401090-54-7 (S)-quinuclidin-3-yl 2-(4-(4-fluorophenyl)thiazol-2-yl)propan-2-ylcarbamate 
• 1047672-60-5 (3S)-1-azabicyclo[2.2.2]oct-3-yl (2-phenyl-3-thienyl)carbamate hydrochloride 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 1233329-28-6 (R)-(4-fluoro-phenylamino)-phenyl-acetic acid (R)-(1-azabicyclo[2.2.2]oct-3-yl)ester 
• 1233329-45-7 (R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)-acetate 

Relevant articles and documents

Borneol dehydrogenase from Pseudomonas sp. TCU-HL1 possesses novel quinuclidinone reductase activities

Borneol dehydrogenase (BDH) catalyses the last step of the camphor biosynthetic pathway in plants and the first reaction in the borneol degradation pathway in soil microorganisms. Native or engineered BDH can be used to produce optically pure borneol and camphor. The recently reported apo-form crystal structure of BDH (PDB ID: 6M5N) from Pseudomonas sp. TCU-HL1 superimposes well with that of 3-quinuclidinone reductase (QR) (PDB ID: 3AK4) from Agrobacterium tumefaciens. QR catalyses the conversion of 3-quinuclidinone into (R)-3-(?)-quinuclidinol, an important chiral synthone for several drugs. However, the kinetic parameter, kcat, of QR was not determined in the previous reports even though both BDH and QR have various potential industrial applications. Here, we aimed to further characterise their structural and functional relationship. Recombinant QR with the native sequence was cloned, expressed in E. coli, and purified. We found that 3-quinuclidinone can be used as an alternative substrate for BDH. Only (R)-3-(?)-quinuclidinol was detected in this BDH-catalysed reaction. The results of 3 D molecular docking simulation show that 3-quinuclidinone and (+)-/(-)- borneol were docked to two different parts of the QR active site. In contrast, all three compounds are docked uniformly to the alpha-1 helix of BDH. There results explain why BDH can turnover 3-quinuclidinone, while QR can not act on (+)-/(-)-borneol.

Industrially viable preparation of (R)-3-Quinuclidinol, a key building block of muscarine M1, M3 agonists and M3 antagonists

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A process for producing 3-quinuclidinone hydrochloride by oxidation of unwanted isomer 3-S-quinuclidinol

An industrially efficient method was developed synthetic process for the preparation of 3-quinuclidinone HCl by recycling of 3-S-quinuclidinol in one step sequence of oxidation process. Oxidation of secondary alcohol of 3-S-quinuclidinol which utilises complexes of a sulfide such as dimethyl sulfide with N-chlorosuccinimide to give target compound in high yield.