35423-17-7

Basic information

• Product Name: 3-QUINUCLIDINONE OXIME
• Synonyms: 3-QUINUCLIDINONE OXIME
• CAS NO: 35423-17-7
• Molecular Formula: C7H12N2O
• Molecular Weight: 140.18
• Mol File: 35423-17-7.mol
• Article Data: 32

Chemical Properties

• Melting Point: 223-225°C
• Boiling Point: 261°Cat760mmHg
• Flash Point: 111.7°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 0.00352mmHg at 25°C
• CAS DataBase Reference: 3-QUINUCLIDINONE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 3-QUINUCLIDINONE OXIME(35423-17-7)
• EPA Substance Registry System: 3-QUINUCLIDINONE OXIME(35423-17-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 35423-17-7(Hazardous Substances Data)

Usage

General Description

3-Quinuclidinone oxime is a chemical compound that is commonly used as a reagent in organic synthesis. It is a white crystalline solid that is soluble in water and possesses a distinct odor. It is often utilized as a protecting group for amino compounds and as a precursor for other chemical reactions. 3-Quinuclidinone oxime can also act as a chelating agent in metal ion extraction processes and has been studied for its potential use in pharmaceutical and medicinal applications. However, it is important to handle this chemical with care as it may pose certain health risks if not used properly.

InChI:InChI=1/C7H12N2O.ClH/c10-8-7-5-9-3-1-6(7)2-4-9;/h6,10H,1-5H2;1H/b8-7+;

Upstream product

• 76883-37-9 3-hydroxyimino quinuclidine hydrochloride 
• 3731-38-2 3-Quinuclidinone 
• 5470-11-1 hydroxylamine hydrochloride 
• 1193-65-3 3-quinuclidinone hydrochloride 

Downstream Products

• 695184-05-5 4-(6-bromo-pyridazin-3-yl)-1, 4-diazabicyclo [3.2. 2] nonane 
• 695183-61-0 4-biphenyl-4-yl-1,4-diazabicyclo[3. 2. 2]nonane fumaric acid salt 
• 677723-95-4 4-(5-phenyl-1,3,4-thiadiazol-2-yl)-1,4-diazabicyclo[3.2.2]nonane 
• 677723-97-6 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-phenyl-1,3,4-oxadiazole 
• 283-38-5 1,4-diazabicyclo[3.2.2]nonane 

Relevant articles and documents

Structure-property relationship of quinuclidinium surfactants-Towards multifunctional biologically active molecules

Motivated by diverse biological and pharmacological activity of quinuclidine and oxime compounds we have synthesized and characterized novel class of surfactants, 3-hydroxyimino quinuclidinium bromides with different alkyl chains lengths (CnQNOH; n = 12, 14 and 16). The incorporation of non conventional hydroxyimino quinuclidinium headgroup and variation in alkyl chain length affects hydrophilic-hydrophobic balance of surfactant molecule and thereby physicochemical properties important for its application. Therefore, newly synthesized surfactants were characterized by the combination of different experimental techniques: X-ray analysis, potentiometry, electrical conductivity, surface tension and dynamic light scattering measurements, as well as antimicrobial susceptibility tests. Comprehensive investigation of CnQNOH surfactants enabled insight into structure-property relationship i.e., way in which the arrangement of surfactant molecules in the crystal phase correlates with their solution behavior and biologically activity. The synthesized CnQNOH surfactants exhibited high adsorption efficiency and relatively low critical micelle concentrations. In addition, all investigated compounds showed very potent and promising activity against Gram-positive and clinically relevant Gram-negative bacterial strains compared to conventional antimicrobial agents: tetracycline and gentamicin. The overall results indicate that bicyclic headgroup with oxime moiety, which affects both hydrophilicity and hydrophobicity of CnQNOH molecule in addition to enabling hydrogen bonding, has dominant effect on crystal packing and physicochemical properties. The unique structural features of cationic surfactants with hydroxyimino quinuclidine headgroup along with diverse biological activity have made them promising structures in novel drug discovery. Obtained fundamental understanding how combination of different functionalities in a single surfactant molecule affects its physicochemical properties represents a good starting point for further biological research.

Structure-based design of highly selective 2,4,5-trisubstituted pyrimidine CDK9 inhibitors as anti-cancer agents

Cyclin-dependent kinases (CDKs) are a family of Ser/Thr kinases involved in cell cycle and transcriptional regulation. CDK9 regulates transcriptional elongation and this unique property has made it a potential target for several diseases. Due to the conserved ATP binding site, designing selective CDK9 inhibitors has been challenging. Here we report our continued efforts in the optimization of 2,4,5-tri-substituted pyrimidine compounds as potent and selective CDK9 inhibitors. The most selective compound 30m was >100-fold selective for CDK9 over CDK1 and CDK2. These compounds showed broad anti-proliferative activities in various solid tumour cell lines and patient-derived chronic lymphocytic leukaemia (CLL) cells. Decreased phosphorylation of the carboxyl terminal domain (CTD) of RNAPII at Ser-2 and down-regulation of anti-apoptotic protein Mcl-1 were confirmed in both the ovarian cancer model A2780 and patient-derived CLL cells.

Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations

New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.