20098-16-2

Usage

Uses

Used in Chemical Industry:
1,4-Adamantandiol is used as a valuable intermediate in the synthesis of various compounds, contributing to the development of new chemical products and materials.
Used in Pharmaceutical Industry:
1,4-Adamantandiol is used as a key building block in the creation of pharmaceutical compounds, potentially leading to the discovery of new drugs and therapeutic agents. Its unique structure and properties make it a promising candidate for various medicinal applications.

Upstream product

• 20098-14-0 chemantane 
• 281-23-2 adamantane 
• 700-58-3 2-Adamantanone 
• 700-57-2 1-adamantanol 
• 112185-87-2 4-Nitro-benzenesulfonic acid (1R,2S,3S,5S)-5-hydroxy-adamantan-2-yl ester 
• 68193-15-7 1,4-diacetoxyadamantane 

Downstream Products

• 1342302-61-7 C₆H₁₅N*C₂₃H₂₇O₆P 

Relevant academic research and scientific papers

A new one-step method for oxaadamantane synthesis

Oxidation of 2-methyl-2-hydroxyadamantane by trifluoroperacetic acid in trifluoroacetic acid gives oxaadamantane and exo-2-oxaadamantane-4-ol in a good yield. Other 2-hydroxyadamantane derivatives do not undergo this transformation. An oxidative cleavage and subsequent cyclization mechanism is proposed.

Photoacetylation of 2-Substituted Adamantanes. Stereochemistry and Substituent Effects

Photoacetylation of 2-substituted adamantanes with biacetyl gave regiospecifically syn- and anti-4-substituted 1-acetyladamantanes.Competitive reactions for two syn and anti δ-hydrogen abstractions by triplet biacetyl showed that the ρ* values were -0.50 and -0.79, respectively.The carbon-13 NMR was studied in order to assign stereoisomers.The observed magnitude of the field-effect transmission for two series of substituent effects was understandable on the basis of the geometrical relationships (bond length and angle) between the reaction center and a substituent.

Biocatalytic production of 5-hydroxy-2-adamantanone by P450cam coupled with NADH regeneration

5-Hydroxy-2-adamantanone is a versatile starting material for the synthesis of various adamantane derivatives. In this study, we investigated the biocatalytic production of 5-hydroxy-2-adamantanone using P450cam monooxygenase coupled with NADH regeneration. We constructed Escherichia coli cells that expressed P450cam and its redox partners, putidaredoxin and putidaredoxin reductase, and cells that co-expressed this P450cam multicomponent system with a glucose dehydrogenase (Gdh) to regenerate NADH using glucose. Two types of cells - wet cells that did not receive any treatment after washing with glycerol-containing buffer, and freeze-dried cells that were lyophilized after the washing - were prepared as whole-cell catalysts. When wet cells were reacted with 2-adamantanone, E. coli cells expressing only the P450cam multicomponent system efficiently produced 5-hydroxy-2-adamantanone in the presence of glucose. However, the co-expression of this P450cam system with Gdh did not further enhance the amount of this product. These results indicate that enough amounts of NADH for P450cam catalysis would be supplied by endogenous glucose metabolism in the E. coli host. In contrast, when freeze-dried cells were used, only the cells co-expressing the P450cam multicomponent system with Gdh efficiently catalyzed the oxidation in the presence of glucose. These results suggest that the exogenous Gdh compensated loss of NADH regeneration by the endogenous glucose metabolism that would be damaged by the lyophilization process. Furthermore, we attempted to produce 5-hydroxy-2-adamantanone with repeated additions of the substrate using wet cells expressing only the P450cam multicomponent system and freeze-dried cells co-expressing this P450cam system with Gdh. These whole-cell catalysts attained high-yield production; the wet cells and the freeze-dried cells produced 36 mM (5.9 g/l) and 21 mM (3.5 g/l) of 5-hydroxy-2-adamantanone, respectively.

Phosphates of bridgehead alcohols as putative inositol monophosphatase inhibitors: Molecular design and synthetic approach

To enhance the lipophilicity of d-3,5,6-trideoxyinositol monophosphate, the IMPase inhibitor, its bridgehead analogues were suggested on the basis of molecular modeling. Adamantane-1,2- and 1,4-diols were converted into their 1-phosphates via the step of

CARBAMATE AND UREA INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1

This invention relates to novel compounds of the invention pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of cortisol in a cell or the inhibition of the conversion of cortisone to cortisol in a cell.

POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS

A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising recurring units containing a non-leaving hydroxyl group represented by formula (1) wherein R1 is H, methyl or trifluoromethyl, Y is H or OH, at least one Y being OH, and the wavy line indicates an indefinite direction of the bond. The composition is improved in resolution when processed by lithography.

Synthetic approach to preparation of polycyclic compounds possessing physiological activity: I. Synthesis of 1,4-disubstituted adamantanes with amino acid fragment

In the present publication various synthetic procedures are reported for previously unknown 1,4-disubstituted adamantanes, containing in particular in position 1 an amino acid fragment (N-benzoyl-β-alanyloxy group). The procedures developed for modification of functional groups in the adamantane skeleton provide a possibility of synthesis of compounds with potential anticancer activity.

Site selective oxidation of tricyclo3,7>decane (adamantane) and some of its derivatives using fungi of the genus Absidia

Tricyclo3,7>decane 1a has been converted into 1-hydroxytricyclo3,7>decane 1b, tricyclo3,7>decane-1,4ax-diol 4b, tricyclo3,7>decane-1,3-diol 3b and to a lesser extent, 2-hydroxytricyclo3,7>decane 4a (20 to 40percent overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var. nigra (IMI 240053) as biocatalysts.In addition, A. cylindrospora (IMI 342950) converted tricyclo3,7>decane-1-carboxylic acid 1c into 4ax-hydroxytricyclo3,7>decane-1-carboxylic acid 4c with almost complete regioselectivity.Tricyclo3,7>decane derivatives 1d-g were used as biohydroxylation substrates with A. cylindrospora (IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position.The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.

CHARGE DISPERSAL IN 1- AND 2-ADAMANTYL CATIONS

Substituents at the remoter 5-position of 2-adamantyl arylsulfonates controlsolvolysis rates more strongly than substituents the 4-position.