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 
• 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 
• 768-95-6 1-adamanthanol 
• 36960-53-9 1-trimethylsiloxyadamantane 
• 14651-42-4 1-(bromomethyl)adamantane 
• 150587-69-2 1-[(1E)-prop-1-en-1-yl]adamantane 

Downstream Products

• 16269-16-2 3-(1-adamantyl)propanoic acid 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 20778-55-6 1-n-propyladamantane 
• 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 
• 39978-68-2 α-methyl-1-adamantylethylamine hydrochloride 
• 39917-51-6 1-(1-adamantyl)-2-propanol 
• 20778-55-6 1-n-propyl-adamantane 
• 56558-44-2 1-(1-Adamantyl)-2-N-benzylaminopropan 
• 39978-69-3 [2-(adamantan-1-yl)-1-methyl]ethylamine 

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.

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).

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.