13858-85-0

Basic information

• Product Name: Cyclohexanone O-methyl oxime
• Synonyms: Cyclohexanone O-methyl oxime
• CAS NO: 13858-85-0
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.1842
• Mol File: 13858-85-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 173.8°Cat760mmHg
• Flash Point: 52.1°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 1.67mmHg at 25°C
• Refractive Index: 1.487
• CAS DataBase Reference: Cyclohexanone O-methyl oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone O-methyl oxime(13858-85-0)
• EPA Substance Registry System: Cyclohexanone O-methyl oxime(13858-85-0)

Safety Data

• Hazardous Substances Data: 13858-85-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 22, p. 1024, 1957 DOI: 10.1021/jo01360a007

InChI:InChI=1/C7H13NO/c1-9-8-7-5-3-2-4-6-7/h2-6H2,1H3

Upstream product

• 67-62-9 O-Methylhydroxylamin 
• 108-94-1 cyclohexanone 
• 100-64-1 cyclohexanone-oxime 
• 77-78-1 dimethyl sulfate 
• 1122-60-7 1-nitrocyclohexane 
• 593-56-6 N-methoxylamine hydrochloride 
• 74-88-4 methyl iodide 
• 2181-42-2 trimethylsulphonium iodide 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 19731-71-6 cyclohexanone-O-(phenylmethyl)oxime 
• 14371-10-9 (E)-3-phenylpropenal 
• 105532-86-3 N,O-bis(trimethylsilyl)-N-methoxycarbamate 
• 67-56-1 methanol 

Downstream Products

• 4278-87-9 dicyclohexylidenehydrazine 
• 108-94-1 cyclohexanone 
• 134023-73-7 2-(1-Methoxyamino-cyclohexyl)-propan-2-ol 
• 105-60-2 caprolactam 
• 193805-51-5 3-Methyl-3-phenyl-1,2,4-trioxaspiro[5.4]decane 
• 67-62-9 O-Methylhydroxylamin 
• 19731-71-6 cyclohexanone-O-(phenylmethyl)oxime 
• 502-42-1 cycloheptanone 
• 1443469-88-2 2,2,2-trifluoro-N-[1-(4-methoxyphenyl)cyclohexyl]acetamide 
• 1443469-77-9 C₉H₁₂F₃NO₂ 

Relevant articles and documents

Activity-based protein profiling reveals that secondary-carbon-centered radicals of synthetic 1,2,4-trioxolanes are predominately responsible for modification of protein targets in malaria parasites

Endoperoxide-containing antimalarials, such as artemisinin and the synthetic trioxolane OZ439, are prodrugs activated by heme to generate primary and secondary carbon-centered radicals. We employed activity-based protein profiling (ABPP) to show that the

Titanium-Mediated Synthesis of Spirocyclic NH-Azetidines from Oxime Ethers

The TiIV-mediated synthesis of spirocyclic NH-azetidines from oxime ethers using either an alkyl Grignard reagent or terminal olefin ligand exchange coupling partner is described. Through a proposed Kulinkovich-type mechanism, a titanacyclopropane intermediate forms and serves as a 1,2-aliphatic dianion equivalent, inserting into the 1,2-dielectrophilc oxime ether to ultimately give rise to the desired N-heterocyclic four-membered ring. This transformation proceeds in moderate yield to furnish previously unreported and structurally diverse NH-azetidines in a single step.

Rationale design of biotinylated antimalarial endoperoxide carbon centered radical prodrugs for applications in proteomics

The semisynthetic artemisinin derivatives such as artesunate and artemether, along with the fully synthetic endoperoxide antimalarials (e.g., OZ277, Nature 2004, 430, 900-904), are believed to mediate their antimalarial effects by iron-induced formation of carbon-centered radicals capable of alkylating heme and/or protein. Here, we describe the design and synthesis of a series of biotinylated endoperoxide probe molecules for use in proteomic studies. The target molecules include derivatives of the artemisinin and OZ families, and we demonstrate that these conjugates express nanomolar in vitro activity versus cultured strains of Plasmodium falciparum. We also describe the synthesis of chemically cleavable linked conjugates designed to enable mild elution of labeled proteins during target protein identification.