38614-06-1

Basic information

• Product Name: 2-((3r,5r,7r)-adamantan-1-yl)phenol
• Synonyms: 2-((3r,5r,7r)-adamantan-1-yl)phenol
• CAS NO: 38614-06-1
• Molecular Weight: 228.334
• Mol File: 38614-06-1.mol

Chemical Properties

• CAS DataBase Reference: 2-((3r,5r,7r)-adamantan-1-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((3r,5r,7r)-adamantan-1-yl)phenol(38614-06-1)
• EPA Substance Registry System: 2-((3r,5r,7r)-adamantan-1-yl)phenol(38614-06-1)

Safety Data

• Hazardous Substances Data: 38614-06-1(Hazardous Substances Data)

Usage

Type of compound

Phenolic compound

Contains

An adamantan-1-yl group

Derived from

Phenol

Structure

Rigid, cage-like adamantane structure

Classification

Tertiary alcohol

Uses

Intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Value

Unique structure and properties useful in various industrial and research applications

Upstream product

• 935-56-8 1-chloroadamantane 
• 108-95-2 phenol 
• 109-99-9 tetrahydrofuran 
• 16200-57-0 Toluene-4-sulfonic acid adamantan-1-yl ester 
• 139-02-6 sodium phenoxide 
• 768-95-6 1-adamanthanol 
• 768-90-1 1-Adamantyl bromide 
• 1357000-33-9 2-((3r,5r,7r)-adamantan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 41031-34-9 α-(1-adamantyl)cyclohexanone 
• 41031-37-2 2-(1-Adamantyl)-cyclohexanol 

Relevant articles and documents

Enantiospecific sp2–sp3 Coupling of ortho- and para-Phenols with Secondary and Tertiary Boronic Esters

The coupling of ortho- and para-phenols with secondary and tertiary boronic esters has been explored. In the case of para-substituted phenols, after reaction of a dilithio phenolate species with a boronic ester, treatment with Ph3BiF2 or Martin's sulfurane gave the coupled product with complete enantiospecificity. The methodology was applied to the synthesis of the broad spectrum antibacterial natural product (?)-4-(1,5-dimethylhex-4-enyl)-2-methyl phenol. For ortho-substituted phenols, initial incorporation of a benzotriazole on the phenol oxygen atom was required. Subsequent ortho-lithiation and borylation gave the coupled product, again with complete stereospecificity.

Alkylation of aromatic compounds with 1-bromoadamantane in the presence of metal complex catalysts

Synthesis of aryladamantanes was performed by reaction of 1-bromoadamantane with aromatic compounds in the presence of metal complex catalysts containing Mo, Cr, W, Cu, and Co.

The structure, photochemical reactivity, and photophysical properties of adamantyl X-substituted aryl ethers and a comparison with the alkyl groups, methyl, tert-butyl, and allyl

The structure, photophysical properties, and photochemistry of the adamantyl aryl ethers 1 in both methanol and cyclohexane have been examined. UV absorption spectra, 13C NMR chemical shifts, X-ray structures, and Gaussian calculations (B3LYP/6-31G(d)) indicate that these ethers adopt a 90° conformer in the ground state. In contrast, fluorescence spectra, excited singlet state lifetimes, and calculations (TDDFT) indicated a 0° conformer is preferred in the first excited singlet state S1. Irradiation in either solvent results in the formation of adamantane and the corresponding phenol as the major products, both derived from radical intermediates generated by homolytic cleavage of the ether bond. The 4-cyano substituted ether 1j was the only one to form the ion-derived product, 1-methoxyadamantane (16% yield), on irradiation in methanol. Rate constants of bond cleavage for these ethers from S1 were estimated by two different methods by comparison with the unreactive anisoles 2, but the effect of substituents was too small to determine structure-reactivity correlations. The temperature dependence of the quantum yields of the fluorescence of the unsubstituted, 4-methoxy and 4-cyano derivatives of 1 and 2 were also determined. These results indicated that the activated process for 1 was mainly bond cleavage for the 4-cyano substrate whereas for 2, it was internal conversion and intersystem crossing.

Non-catalyzed C-alkylation of phenols with cyclic secondary alkyl bromides

C-Alkylations of phenol with 1-chloro and 1-bromoadamantane, 2-bromoadamantane, cyclohexyl bromide and exo-2-bromonorbornane, and C-alkylations of para-substituted phenol derivatives with 2-bromoadamantane are described.

REACTION OF PHENOL WITH 1-HYDROXYADAMANTANE IN THE PRESENCE OF ALUMINUM DIPHENYL DITHIOPHOSPHATE

The reaction of phenol with 1-hydroxyadamantane in the presence of aluminum diphenyl dithiophosphate leads to a mixture of mono-, di-, and tri(1-adamantyl)phenols and 1-adamantyl phenyl ether.As a rule the 2-(1-adamantyl)phenol predominates in the mixture.

REACTION OF exo-2-NORBORNYL AND 1-ADAMANTYL p-TOLUENESULFONATES WITH SODIUM PHENOXIDE IN TETRAHYDROFORAN. IONIZATION OF THE SUBSTRATES UNDER "APPARENTLY-SN2" CONDITIONS

exo-2-Norbornyl and 1-adamantyl tosylates react with sodium phenoxide in tetrahydrofuran via ionization, most probably through a cyclic transition state.The results call for attention in interpreting substitution reactions under "apperently-SN2" conditions.