20134-98-9

Basic information

• Product Name: Acetaldehyde, O-(phenylmethyl)oxime
• CAS NO: 20134-98-9
• Molecular Formula: C9H11NO
• Molecular Weight: 149.192
• Mol File: 20134-98-9.mol

Chemical Properties

• CAS DataBase Reference: Acetaldehyde, O-(phenylmethyl)oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Acetaldehyde, O-(phenylmethyl)oxime(20134-98-9)
• EPA Substance Registry System: Acetaldehyde, O-(phenylmethyl)oxime(20134-98-9)

Safety Data

• Hazardous Substances Data: 20134-98-9(Hazardous Substances Data)

Upstream product

• 107-29-9 Acetaldehyde oxime 
• 100-39-0 benzyl bromide 
• 367262-20-2 C₁₃H₁₇NO₂S₂ 
• 20549-72-8 4-phenoxybutyl iodide 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 75-07-0 acetaldehyde 
• 622-33-3 N-benzyloxyamine 

Downstream Products

• 622-33-3 N-benzyloxyamine 
• 220615-88-3 N-(1-(((4'-methoxy(1,1'-biphenyl)-4-yl)sulfonyl)methyl)ethyl)-N-benzyloxy Amine 
• 101518-63-2 (3R,4R)-1-Benzyloxy-3-isopropyl-4-methyl-azetidin-2-one 
• 91078-05-6 1-benzyloxy-3,3-dimethyl-4-methyl-2-azetidinone 

Relevant articles and documents

Iridium(I)-Catalyzed α-C(sp3)-H Alkylation of Saturated Azacycles

Saturated azacycles are commonly encountered in bioactive compounds and approved therapeutic agents. The development of methods for functionalization of the α-methylene C-H bonds of these highly privileged building blocks is of great importance, especially in drug discovery. While much effort has been dedicated toward this goal by using a directed C-H activation approach, the development of directing groups that are both general as well as practical remains a significant challenge. Herein, the design and development of novel amidoxime directing groups is described for Ir(I)-catalyzed α-C(sp3)-H alkylation of saturated azacycles using readily available olefins as coupling partners. This protocol extends the scope of saturated azacycles to piperidines, azepane, and tetrahydroisoquinoline that are incompatible with our previously reported directing group. A variety of olefin coupling partners, including previously unreactive disubstituted terminal olefins and internal olefins, are compatible with this transformation. The selectivity for a branched α-C(sp3)-alkylation product is also observed for the first time when acrylate is used as the reaction partner. The development of practical, one-step installation and removal protocols further adds to the utility of amidoxime directing groups.

Alkoxyamino glycoside acceptors for the regioselective synthesis of oligosaccharides using glycosynthases and transglycosidases

Alkoxyamino derivatives of oligosaccharides have been synthesized by enzymatic synthesis using a glycosynthase and a transglycosidase. The chemoselective assembly of unprotected oligosaccharides bearing glucose at the reducing end with N-alkyl-O-benzylhydroxylamine provides sugar derivatives that are good acceptors for enzymatic synthesis using either glycosynthase or transglycosidase. Furthermore, this method affords the possibility of controlling the regioselectivity of coupling depending on the nature of the alkoxyamino substituent and provides high-yield coupling of sugars without the need for complex protecting group chemistry.

PYRIDINYL DERIVATIVES AS INHIBITORS OF ENZYME NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE

The present application discloses a compound of the formula (I) wherein Q is optionally substituted pyridyl; p is 0-6; Y is formulae (i), (ii) and (iii) where X is =O, =S and =N-CN, r is 1-12, R is -Z-A, Z is a single bond, -S(=O)2-, >P=O, >C=O, -C(=O)NH-, and -C(=S)NH-; and A is hydrogen, C1-12-alkyl, C3-12-cycloalkyl, - [CH2CH2O]1-10-(C1-6-alkyl), C1-12-alkenyl, aryl, heterocyclyl, and heteroaryl; B is a single bond, -NRN-, -S(=O)2- and -O-; wherein RN is selected from hydrogen, C1-12-alkyl, C3-12-cycloalkyl, -[CH2CH2O]1-10-(C1-6-alkyl), C1-12-alkenyl, aryl, heterocyclyl, and heteroaryl; s is 0-6; and Cy is aryl, cycloalkyl, heterocyclyl, and heteroaryl. The compounds are usefuld for use as a medicament for the treatment of a disease or a condition caused by an elevated level of nicotinamide phosphoribosyltransferase (NAMPRT).

Decarboxylative acylation approach of thiohydroxamate esters

A decarboxylative acylation approach is achieved with thiohydroxamate ester 6, which is less reactive and more stable than Barton's ester 1.

Tin-free radical acylation reactions with methanesulfonyl oxime ether

A simple strategy involving thermal decomposition of the methanesulfonyl radical into the methyl radical and the subsequent transfer of an iodine atom or phenyl telluride group was used to develop a tin-free radical acylation reaction (see scheme; V-40 = 1,1′-azobis(cyclohexane-1-carbonitrile). The key was finding reaction conditions under which the I or PhTe transfer is faster than the direct addition of the alkyl radical to the methanesulfonyl ether.

Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates

A general method for the stereoselective coupling of unprotected oligosaccharides with any substrate containing a N,O-disubstituted hydroxylamine group is described. The cyclic nature of the oligosaccharide reducing unit is preserved and the substrate glycosylated with high diastereoseletivity to sugar through an amino (N[OR2]-) or art aminoxy (N[R1]-O-) linkage. Due to the uniquely high chemical reactivity and specificity of disubstituted hydroxylamine toward the sugar reducing end, neither protecting groups nor activation methods are required to perform the reaction in aqueous solution. The characteristic features and the scope of this new type of glycosylation reaction are exemplified for the chemoselective synthesis of model glycopeptides.

Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, amd Nitrones. A Convenient Route to Synthesis of β-Amino Alcohol

The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode.The product, β-methoxyamino alcohol was easily converted to β-amino alcohol by simple reduction.A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime.The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction.Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.

ADDITION OF ARYLLITHIUM COMPOUNDS TO OXIME ETHERS

Addition of non-stabilized organolithium reagents to O-alkyl aldoximes in the presence of boron trifluoride etherate gives rise to O-alkyl hydroxylamines.The Z oxime isomer preferentially reacts under these reaction conditions.