149649-90-1

Basic information

• Product Name: Hydroxylamine, O-(3-phenyl-2-propynyl)- (9CI)
• Synonyms: Hydroxylamine, O-(3-phenyl-2-propynyl)- (9CI)
• CAS NO: 149649-90-1
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17386
• Mol File: 149649-90-1.mol

Chemical Properties

• Boiling Point: 281.0±23.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• PKA: 2.90±0.70(Predicted)
• CAS DataBase Reference: Hydroxylamine, O-(3-phenyl-2-propynyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxylamine, O-(3-phenyl-2-propynyl)- (9CI)(149649-90-1)
• EPA Substance Registry System: Hydroxylamine, O-(3-phenyl-2-propynyl)- (9CI)(149649-90-1)

Safety Data

• Hazardous Substances Data: 149649-90-1(Hazardous Substances Data)

Upstream product

• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 108-86-1 bromobenzene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 188720-10-7 2-(3-Phenyl-prop-2-ynyloxy)-isoindole-1,3-dione 

Downstream Products

• 1287768-63-1 isopropyl (3-phenyl-2-propynyl)oxycarbamate 
• 1287768-62-0 benzyl (3-phenyl-2-propynyl)oxycarbamate 
• 101774-26-9 4-bromo-3-phenylisoxazole 
• 23253-50-1 4-iodo-3-phenylisoxazole 
• 1287769-00-9 benzyl 2,5-dihydro-4-iodo-3-phenyl-2H-isoxazole-2-carboxylate 
• 1287769-01-0 C₁₂H₁₂INO₃ 
• 1287769-02-1 C₁₃H₁₄INO₃ 
• 1287769-03-2 C₁₄H₁₆INO₃ 
• 1287769-04-3 C₂₄H₁₈INO₃ 
• 1287769-31-6 benzyl 2,5-dihydro-3-phenyl-4-((trimethylsilyl)ethynyl)-2H-isoxazole-2-carboxylate 
• 1287769-32-7 benzyl 2,5-dihydro-3-phenyl-4-(2-thienyl)-2H-isoxazole-2-carboxylate 
• 1287769-33-8 benzyl 2,5-dihydro-4-((E)-2-(methoxycarbonyl)ethenyl)-3-phenyl-2H-isoxazole-2-carboxylate 

Relevant articles and documents

Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2,5-dihydroisoxazoles and isoxazoles

An efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2,5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2,5-dihydro-derivative.

Design and synthesis of m1-selective muscarinic agonists: (R)-(-)-(Z)- 1-azabicyclo[2.2.1]heptan-3-one, O-(3-(3'-methoxyphenyl)-2-propynyl)-oxime maleate (CI-1017), a functionally m1-selective muscarinic agonist

The synthesis and SAR of a series of (Z)-(±)-1- azabicyclo[2.2.1]heptan-3-one, O-(3-aryl-2-propynyl)oximes are described. The biochemistry and pharmacology of 24Z (PD 142505) and its enantiomers are highlighted. 24Z is functionally an m1-selective muscari

Synthesis and biological characterization of 1,4,5,6- tetrahydropyrimidine and 2-amino-3,4,5,6-tetrahydropyridine derivatives as selective m1 agonists

Previous studies identified several novel tetrahydropyrimidine derivatives exhibiting muscarinic agonist activity in rat brain. Such compounds might be useful in treating cognitive and memory deficits associated with low acetylcholine levels, as found in Alzheimer's disease. To determine the molecular features of ligands important for binding and activity at muscarinic receptor subtypes, the series of tetrahydropyrimidines was extended. Several active compounds were examined further for functional selectivity through biochemical studies of muscarinic receptor activity using receptor subtypes expressed in cell lines. Several amidine derivatives displayed high efficacy at m1 receptors and lower activity at m3 receptors coupled to phosphoinositide (PI) metabolism in A9 L cells. Four ligands, including 1b, 1f, 2b, and 7b, exhibited marked functional selectivity for m1 vs m3 receptors. Compound 1f also exhibited low activity at m2 receptors coupled to the inhibition of adenylyl cyclase in A9 L cells. Molecular modeling studies also were initiated to help understand the nature of the interaction of muscarinic agonists with the m1 receptor using a nine amino model of the m1 receptor. Several important interactions were identified, including interactions between the ester moiety and Thr192. Additional interactions were found for oxadiazoles and alkynyl derivatives with Asn382, suggesting that enhanced potency and selectivity may be achieved by maximizing interactions with Asp105, Thr192, and Ash382. Taken together, the data indicate that several amidine derivatives display functional selectivity for m1 muscarinic receptors, warranting further evaluation as therapeutic agents for the treatment of Alzheimer's disease. In addition, several amino acid residues were identified as potential binding sites for m1 agonists. These data may be useful in directing efforts to develop even more selective m1 agonists.