1619-34-7

Basic information

• Product Name: 3-Quinuclidinol
• Synonyms: 1-AZABICYCLO[2.2.2]OCTAN-3-OL;3-HYDROXYCHINUCLIDIN;3-QUINUCLIDINOL;3-HYDROXYQUINUCLIDINE;3-HYDROXYQUINUELIDINE;3-Hydroxy-1-azabicyclo[2.2.2]octane;Quinuclidine-3-ol;Quinuclidinol
• CAS NO: 1619-34-7
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18
• EINECS: 216-578-4
• Product Categories: Pharmaceutical material and intermeidates;Quinuclidine derivatives;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1619-34-7.mol

Chemical Properties

• Melting Point: 220-223 °C(lit.)
• Boiling Point: 235.98°C (rough estimate)
• Flash Point: 97.7 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.0083 (rough estimate)
• Vapor Pressure: 0.0545mmHg at 25°C
• Refractive Index: 1.4790 (estimate)
• Storage Temp.: 2-8°C
• PKA: 14.75±0.20(Predicted)
• Water Solubility: soluble
• Sensitive: Air Sensitive
• Merck: 14,8082
• BRN: 104327
• CAS DataBase Reference: 3-Quinuclidinol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinuclidinol(1619-34-7)
• EPA Substance Registry System: 3-Quinuclidinol(1619-34-7)

Safety Data

• Hazard Codes: C,F
• Statements: 34-11
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 3263 8/PG 2
• WGK Germany: 3
• RTECS: VD6191700
• F: 34
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1619-34-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Quinuclidinol is used as a chiral building block for the development of various antimuscarinic agents and other active pharmaceutical ingredients. Its unique structure allows it to play a crucial role in the preparation of cholinergic receptor ligands and anesthetics, making it an essential component in the synthesis of these drugs.
Used in Chemical Industry:
3-Quinuclidinol serves as a catalyst for the condensation of methyl vinyl ketone with aldehydes, facilitating important chemical reactions in the synthesis of various compounds. Additionally, it is used as a reagent for the cleavage of beta-keto and vinylogous beta-keto esters, further expanding its utility in chemical synthesis.
Used in Hypotensive Applications:
3-Quinuclidinol is also utilized in the development of hypotensive drugs, which help lower blood pressure and are essential for the treatment of hypertension and related cardiovascular conditions.
Used in Organic Chemistry:
3-Quinuclidinol plays a significant role as a synthon in the chemoselective alpha-iodination of acrylic esters through the Morita-Baylis-Hillman reaction, which is an important synthetic method in organic chemistry for the preparation of various complex molecules.

Hazard

Mutation.

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

Upstream product

• 59653-42-8 (-)-Aceclidine 
• 221671-41-6 (S)-quinuclidin-3-yl benzoate 
• 65732-89-0 quinuclidin-3-yl butyrate b 
• 603121-51-3 isobutyric acid 1-aza-bicyclo[2.2.2]oct-3-yl ester 
• 827-61-2 3-acetoxyquinuclidine 
• 3731-38-2 3-Quinuclidinone 
• 1838-39-7 ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 946513-99-1 4-nitrobenzoic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester fumarate 
• 1200405-02-2 (S)-quinuclidin-3-ol butyric acid salt 
• 34286-16-3 2-ethoxycarbonyl-3-quinuclidinone 
• 73997-55-4 3-Hydroxy-1-[2-(4-nitro-phenyl)-ethyl]-1-azonia-bicyclo[2.2.2]octane 

Downstream Products

• 124838-74-0 (S)-1-Butyl-3-hydroxy-1-azonia-bicyclo[2.2.2]octane; bromide 
• 124838-73-9 (S)-1-Hexyl-3-hydroxy-1-azonia-bicyclo[2.2.2]octane; bromide 
• 124838-79-5 3S-benzyloxy-4RS-(2'-hydroxyethyl)-1-benzylpiperidine 
• 124838-75-1 3S-benzyloxy-1-benzylquinuclidinium chloride 
• 124838-72-8 (S)-N-benzyl-3-hydroxyquinuclidinium chloride 
• 102585-08-0 9H-Xanthene-9-carboxylic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester 
• 107757-79-9 (S)-2-Hydroxy-2-phenyl-propionic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester 
• 107757-79-9 (R)-2-Hydroxy-2-phenyl-propionic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester 
• 107770-18-3 3(S)-<<(3-oxo-4(R),7,7-trimethyl-2-oxabicyclo<2.2.1>hept-1(S)-yl)carbonyl>oxy>-1-azabicyclo<2.2.2>octane 
• 81039-90-9 (S)-(+)-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-(4-aminophenyl)-α-phenylacetate 
• 91704-71-1 (-)-2S,3'R-3-quinuclidinyl 2-(3-thienyl)-2-cyclohexyl-2-hydroxy-acetate 
• 91704-71-1 (+)-2R,3'R-3-quinuclidinyl 2-(3-thienyl)-2-cyclohexyl-2-hydroxy-acetate 
• 82326-69-0 (S)-1-azabicyclo<2.2.2>-oct-3-yl-(R,S)-α-hydroxy-α-(4-bromophenyl)-α-phenylacetate 
• 139563-14-7 (S,S)-IQNB 

Relevant articles and documents

Asymmetric hydrogenation of bicyclic ketones catalyzed by BINAP/IPHAN-Ru(II) complex

(Equation Presented). Hydrogenation of 3-quinuclidinone and bicyclo[2.2.2]octan-2-one with a combined catalyst system of RuCl 2[(S)-binap][(R)-iphan] and t-C4H9OK in 2-propanol afforded the chiral alcohols in 97-98% ee. 2-Diphenylmethyl-3- quinuclidinone was hydrogenated with the same catalyst to the cis alcohol with perfect diastereo-and enantioselectivity. The reaction of unsymmetrical ketones with a bicyclo[2.2.1] or-[2.2.2] skeleton gave the corresponding alcohols with high stereoselectivity.

Microbial stereospecific reduction of 3-quinuclidinone with newly isolated Nocardia sp. and Rhodococcus erythropolis

Two bacterium strains, Nocardia sp. WY1202 and Rhodococcus erythropolis WY1406, were isolated from soil samples. They catalyzed the asymmetric reduction of 3-quinuclidinone to give enantiomeric pure (R)- and (S)-3-quinuclidinol, respectively. The optimal temperatures for the bioreduction by Nocardia sp. and R. erythropolis were 30 °C and 37 °C, respectively, while both strains showed highest activity at pH 8.0. Without external addition of expensive NADH or NADPH, (R)-3-quinuclidinol and (S)-3-quinuclidinol were obtained with 93% and 92% isolated yield and >99% enantiomeric excess. As such, microbial reduction by Nocardia sp. WY1202 or R. erythropolis WY1406 offers a new stereospecific approach to both antipodes of 3-quinuclidinol of pharmaceutical importance.

Interactions of chiral quinuclidin-3-yl benzoates with butyrylcholinesterase: Kinetic study and docking simulations

Both enantiomers of quinuclidin-3-yl benzoate (RQBz and SQBz) were synthesized in order to examine the stereoselectivity of the hydrolysis of these esters catalyzed by horse serum butyrylcholinesterase (BChE). The hydrolysis of benzoylcholine (BzCh) was a

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.

Pincerlike molybdenum complex and preparation method thereof, catalytic composition and application thereof, and alcohol preparation method

The invention discloses a clamp-type molybdenum complex, a preparation method, a corresponding catalyst composition and application. The method comprises the steps: obtaining 9 molybdenum complexes with different structures through coordination reaction of 2-(substituent ethyl)-(5, 6, 7, 8-tetrahydroquinolyl) amine and a corresponding carbonyl molybdenum metal precursor; and catalyzing a ketone compound transfer hydrogenation reaction through a molybdenum complex to generate 40 alcohol compounds. The preparation method of the molybdenum complex is simple, high in yield and good in stability. For a transfer hydrogenation reaction of ketone, the molybdenum-based catalytic system has high catalytic activity and small molybdenum loading capacity, is used for production of aromatic and aliphatic alcohols, and has the advantages of simple method, small environmental pollution and high yield.

Preparation method of optical activity 3-quinuclidinol

The invention relates to an intermediate synthesis method, belongs to the field of organic synthesis, and particularly relates to a preparation method of optical activity 3-quinuclidinol with the advantages that the operation is simple and convenient, the cost is low, and the method is suitable for industrial production. An intermediate of 3-quinuclidinol is obtained by using 4-nipecotic acid as astarting material through esterification, nucleophilic substitution, Dieckmann condensation, decarboxylation, salification, reduction, acetylization, chemical resolution and the like. The reaction formula is shown in the description.

Solifenacin succinate raw medicine synthesis process

The invention discloses a solifenacin succinate raw medicine synthesis process. 2-phenylethylamine and 3-quinuclidinone hydrochloride are respectively used as starting raw materials for synthesizing afragment A and a fragment B; then, condensation reaction occurs to generate solifenacin; through salt formation, the solifenacin succinate is obtained. The process is characterized in that straight-chain paraffin and water are used as reaction solvents; alkali metal hydroxides or carbonate and bicarbonates of the alkali metal hydroxides are used as acid-binding agents; phenylethylamine and benzoyl chloride take acylation reaction to generate midbodies 1 of solid precipitation fragments A insoluble in reaction solvents; in the post treatment process, filtering is directly performed; isomers ofthe fragment A are subjected to catalytic racemization through alkali metal hydroxides by using dimethylsulfoxide as a solvent, so that the byproduct isomers can be recovered and utilized; in the second-step reaction post treatment of the fragment B, a conventional pressure reduced distillation method is used for obtaining high-purity and high-yield 3-acetoxyquinine acetate. The invention provides a novel synthesis process with the advantages of high yield and economic and environment-friendly effects, and is suitable for industrial mass production.

The Stereoselective Reductions of Ketones to the Most Thermodynamically Stable Alcohols Using Lithium and Hydrated Salts of Common Transition Metals

A simple method is presented for the highly stereoselective reductions of ketones to the most thermodynamically stable alcohols. In this procedure, the ketone is treated with lithium dispersion and either FeCl2·4H2O or CuCl2·2H2O in THF at room temperature. This protocol is applied to a large number and variety of ketones and is both more convenient and efficient than those commonly reported for the diastereoselective reduction of five- and six-membered cyclic ketones.

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.

"In situ" activation of racemic RuII complexes: Separation of trans and cis species and their application in asymmetric reduction

Ruthenium(II) dichlorides with racemic atropos-biaryl-based diphosphanes and optically active 1,2-diphenylethane-1,2-diamine (DPEN) as ligands have been synthesised. trans and cis isomers were formed due to the low basicity of the diphosphane ligands, in particular, with BITIANP and BIMIP. The trans and cis species were easily separated by filtration. In particular, when rac-BITIANP was used in combination with chiral DPEN, the asymmetric separation of optically pure complexes in cis and trans arrangements was realised and they were used as precatalysts in the asymmetric hydrogenation of ketones. Matching and mismatching combinations exhibited different performances.