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
• Article Data: 46

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

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 1619-34-7 differently. You can refer to the following data:
1. Hypotensive. Synthon for preparation of cholinergic receptor ligands and anesthetics
2. 3-Quinuclidinol acts as a chiral building block for various antimuscarinic agents and other active pharmaceutical ingredients. It serves as a catalyst for condensation of methyl vinyl ketone with aldehydes. It is also used as a reagent for cleavage of beta-keto and vinylogous beta-keto esters. Further, it plays an important role as a synthon in the preparation of cholinergic receptor ligands and anesthetics. In addition to this, it is used in chemoselective alfa-iodination of acrylic esters through Morita-Baylis-Hillman reaction.

Definition

ChEBI: Quinuclidine in which a hydrogen atom at position 3 is substituted by a hydroxy group.

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

• 827-61-2 3-acetoxyquinuclidine 
• 3731-38-2 3-Quinuclidinone 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 6581-06-2 quinuclidinyl benzilate 
• 34286-16-3 2-ethoxycarbonyl-3-quinuclidinone 
• 1838-39-7 ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate 
• 1200405-02-2 (S)-quinuclidin-3-ol butyric acid salt 
• 946513-99-1 4-nitrobenzoic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester fumarate 
• 603121-51-3 isobutyric acid 1-aza-bicyclo[2.2.2]oct-3-yl ester 
• 65732-89-0 quinuclidin-3-yl butyrate b 
• 221671-41-6 (S)-quinuclidin-3-yl benzoate 

Downstream Products

• 62078-97-1 3-(Diphenylacetyloxy)quinuclidine 
• 827-61-2 3-acetoxyquinuclidine 
• 98061-93-9 quinuclidin-3-yl tosylate 
• 13929-94-7 1-azabicyclo[2.2.2]oct-2-ene 
• 33601-77-3 3-chloro-1-azabicyclo[2.2.2]octane hydrochloride 
• 6581-06-2 quinuclidinyl benzilate 
• 3684-26-2 (S)-quinuclidin-3-ol 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 151643-46-8 (2-Ethoxy-phenyl)-carbamic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester; hydrochloride 
• 73997-55-4 3-Hydroxy-1-[2-(4-nitro-phenyl)-ethyl]-1-azonia-bicyclo[2.2.2]octane 
• 100611-34-5 (+/-)-quinuclidin-3-ol; picrate 
• 73997-52-1 N-(β-p-nitrophenylethyl)-3-hydroxyquinuclidinium bromide 
• 80381-20-0 3-(α-Phenylbutyroyloxy)quinuclidine 
• 151643-50-4 3-(2-hexyloxyphenylcarbamoyloxy)quinuclidium chloride 

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.

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

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Assessing the reliability of the NIST library during routine GC-MS analyses: Structure and spectral data corroboration for 5,5-diphenyl-1,3-dioxolan-4-one during a recent OPCW proficiency test

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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.

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.