19835-39-3

Usage

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

• 557-98-2 2-chloropropene 
• 768-95-6 1-adamanthanol 
• 32314-61-7 1-nitroxyadamantane 
• 114310-71-3 1-(bromomagnesiomethyl)adamantane 
• 141-78-6 ethyl acetate 
• 24569-89-9 1,3-dehydroadamantane 
• 67-64-1 acetone 
• 768-90-1 1-Adamantyl bromide 
• 108-22-5 Isopropenyl acetate 
• 935-56-8 1-chloroadamantane 
• 917-54-4 methyllithium 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 6221-74-5 1-methoxyadamantane 
• 36960-53-9 1-trimethylsiloxyadamantane 

Downstream Products

• 20778-55-6 1-n-propyl-adamantane 
• 39917-51-6 1-(1-adamantyl)-2-propanol 
• 39978-68-2 α-methyl-1-adamantylethylamine hydrochloride 
• 350033-94-2 (E)-4-(1-adamantyl)-1-(phenylamino)-1-buten-3-one 
• 350033-96-4 4-(1-adamantyl)-1-(1-piperidyl)but-1-en-3-one 
• 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 
• 419573-71-0 4-(1-adamantyl)-1-(phenylamino)-1-buten-3-one 
• 56558-44-2 1-(1-Adamantyl)-2-N-benzylaminopropan 
• 39978-69-3 [2-(adamantan-1-yl)-1-methyl]ethylamine 

Relevant academic research and scientific papers

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.

IDO inhibitor compound, pharmaceutical compound and application

The invention provides a novel compound. The compound has certain inhibiting activity to indoleamine 2, 3-dioxygenase (IDO) and can be possibly used for treating diseases related to the indoleamine 2, 3-dioxygenase (IDO).

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%.

Synthesis of 1-(2-oxopropyl)adamantane from 1-bromo(chloro)adamantanes and isopropenyl acetate in the presence of iron and manganese compounds

An efficient procedure has been developed for the synthesis of 1-(2-oxopropyl)adamantane by reaction of 1-bromo(chloro)adamantanes with isopropenyl acetate in the presence of manganese and iron compounds.

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.

InCl3/Me3SiBr-catalyzed direct coupling between silyl ethers and enol acetates

A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were also applicable.

α-Alkylation of carbonyl compounds by direct addition of alcohols to Enol acetates

A practical α-alkylation of ketones and aldehydes has been achieved by the direct addition of alcohols to enol acetates. The moderate Lewis acidity of InI3, CaBr3, and FeBr3 is a key factor in the catalytic cycle, and many different alcohols and enol acetates have been successfully used in this procedure.

Asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens

A new asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens has been found. Although alcohols are not the natural substrates for this enzyme, a high R enantioselectivity was observed. Stereochemical studies showed that variations in substrate structure lead to strong variations in enantioselectivity. The highest enantioselectivities are obtained when the β-carbon of the secondary alcohol is tertiary or quaternary.