19835-39-3

Basic information

• Product Name: 1-ADAMANTAN-1-YL-PROPAN-2-ONE
• Synonyms: 1-(1-adamantyl)propan-2-one
• CAS NO: 19835-39-3
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.3
• Mol File: 19835-39-3.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 266.3°Cat760mmHg
• Flash Point: 110°C
• Appearance: /
• Density: 1.037g/cm³
• Vapor Pressure: 0.00874mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: 1-ADAMANTAN-1-YL-PROPAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ADAMANTAN-1-YL-PROPAN-2-ONE(19835-39-3)
• EPA Substance Registry System: 1-ADAMANTAN-1-YL-PROPAN-2-ONE(19835-39-3)

Safety Data

• Hazardous Substances Data: 19835-39-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 51, 1982 DOI: 10.1021/jm00343a010

InChI:InChI=1/C13H20O/c1-9(14)5-13-6-10-2-11(7-13)4-12(3-10)8-13/h10-12H,2-8H2,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 19835-38-2 1-adamantylacetyl chloride 
• 557-98-2 2-chloropropene 
• 768-95-6 1-adamanthanol 
• 32314-61-7 1-nitroxyadamantane 
• 24262-31-5 acetone enolate ion 
• 768-93-4 1-iodoadamantane 
• 102402-84-6 3-(adamantan-1-yl)pentane-2,4-dione 
• 917-54-4 methyllithium 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 108-22-5 Isopropenyl acetate 
• 36960-53-9 1-trimethylsiloxyadamantane 
• 935-56-8 1-chloroadamantane 
• 768-90-1 1-Adamantyl bromide 

Downstream Products

• 39978-69-3 [2-(adamantan-1-yl)-1-methyl]ethylamine 
• 20778-55-6 1-n-propyl-adamantane 
• 39917-51-6 1-(1-adamantyl)-2-propanol 
• 39978-68-2 α-methyl-1-adamantylethylamine hydrochloride 
• 56558-44-2 1-(1-Adamantyl)-2-N-benzylaminopropan 
• 20778-55-6 1-n-propyladamantane 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 16269-16-2 3-(1-adamantyl)propanoic acid 
• 56558-50-0 N-(2-Adamantan-1-yl-1-methyl-ethyl)-N'-(1-methyl-2-phenyl-ethyl)-hydrazine 
• 56558-42-0 N-(2-Adamantan-1-yl-1-methyl-ethyl)-N'-[1-methyl-2-phenyl-eth-(E)-ylidene]-hydrazine 
• 350033-96-4 4-(1-adamantyl)-1-(1-piperidyl)but-1-en-3-one 
• 350033-94-2 (E)-4-(1-adamantyl)-1-(phenylamino)-1-buten-3-one 
• 419573-71-0 4-(1-adamantyl)-1-(phenylamino)-1-buten-3-one 

Relevant articles and documents

Preparation of α-adamantyl-substituted aliphatic ketones

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Exhaustive One-Step Bridgehead Methylation of Adamantane Derivatives with Tetramethylsilane

A methylation protocol of adamantane derivatives was investigated and optimized using AlCl3 and tetramethylsilane as the methylation agent. Substrates underwent exhaustive methylation of all available bridgehead positions with yields ranging from 62 to 86 %, and up to six methyl groups introduced in one step. Scaling-up of the reaction was demonstrated by performing the >40 gram-scale synthesis of 1,3,5,7-tetramethyladamantane with 62 % yield. For several substrates, rearrangements were observed, as well as cleavage of functional groups or Csp3?Csp2 bonds or even cyclohexyl-adamantyl bonds. Based on mechanistic studies, it is suggested that a reactive methylation complex is formed from tetramethylsilane and AlCl3. X-ray diffraction structures of hexamethylated bis-adamantyls reveal elongation or widening of sp3 carbon bonds between adamantyl moieties to 1.585(3) ? and 125.26(9)° due to repulsive H???H contacts.

Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives

The Willgerodt–Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography–mass spectrometry. The reaction time was found to be 3–4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.

InI3/me3sii-catalyzed direct alkylation of enol acetates using alkyl acetates or alkyl ethers

A combined Lewis acid of InI3 and Me3SiI was used to catalyze the direct coupling reactions of enol acetates with alkyl acetates or alkyl ethers without generating metal waste. The easily-handled alkylating reagents enlarged the application area of this coupling reaction. 2011 The Chemical Society of Japan.