18341-84-9

Usage

Uses

Used in Organic Synthesis:
1-(1-ADAMANTYL)PROPAN-1-OL is used as a chiral auxiliary in organic synthesis for its ability to create stereospecific compounds. Its bulky and rigid structure aids in the formation of enantiomerically pure products, which is crucial in the development of pharmaceuticals and other chiral molecules.
Used in Pharmaceutical Industry:
1-(1-ADAMANTYL)PROPAN-1-OL serves as a starting material for the synthesis of other pharmaceutical compounds. Its unique structural properties make it a valuable component in the development of new drugs with specific therapeutic targets.
Used in Advanced Materials Production:
Due to its rigid and stable structure, 1-(1-ADAMANTYL)PROPAN-1-OL has potential applications in the production of advanced materials. These materials could have various uses, such as in the fields of nanotechnology, polymer science, or as components in high-performance materials.
Used in Organometallic Chemistry:
1-(1-ADAMANTYL)PROPAN-1-OL can also be employed as a ligand in organometallic chemistry. Its unique properties may enhance the performance of organometallic complexes, which are widely used in catalysis and other chemical processes.

Upstream product

• 187737-37-7 propene 
• 768-95-6 1-adamanthanol 
• 925-90-6 ethylmagnesium bromide 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 74-96-4 ethyl bromide 
• 24556-17-0 butyl adamantane-1-carboxylate 
• 828-51-3 1-Adamantanecarboxylic acid 
• 1660-05-5 1-(adamantan-1-yl)propan-1-one 

Downstream Products

• 15037-74-8 1-<1-(3-Carboxy-propionyloxy)-propyl>-adamantan 
• 828-51-3 1-Adamantanecarboxylic acid 
• 116137-31-6 1-<1-(3,5-Dimethylphenyl)propyl>adamantane 
• 116137-29-2 1-<1-(4-Tolyl)propyl>adamantane 
• 116137-28-1 1-(1-Phenylpropyl)adamantane 
• 187406-14-0 1-(1-adamantyl)propyl pentamethylbenzenesulfonate 
• 187406-11-7 1-(1-adamantyl)propyl p-toluenesulfonate 
• 187406-07-1 1-(1-adamantyl)propyl p-bromobenzenesulfonate 
• 116137-30-5 1-<1-(3,4-Dimethylphenyl)propyl>adamantane 

Relevant academic research and scientific papers

Preparation of 1-adamantyl ketones: Structure, mechanism of formation and biological activity of potential by-products

Reactions between adamantane-1-carbonyl chloride and several Grignard reagents as well as interactions with solvents have been examined. Some new and unexpected adamantane derivatives were isolated, fully characterized and their biological activity determined. In particular, an unexpected isochromanone 16 was formed in an SEAr process, in which a stable hydrocarbon was the leaving group.

Influence of catalytic system composition on formation of adamantane containing ketones

The preparation of non-symmetrical ketones by the reaction of acyl chlorides and the corresponding Grignard reagents in the presence of catalytic amounts of metal halides is described. The composition of catalyst has a great influence on the yield of the required ketone as well as on side product formation. For each catalytic system, the yield of ketone and the number of side products changes with the time of addition of the Grignard reagent. We examined the influence of both factors in our model reaction of adamantane-1-carbonyl chloride with ethylmagnesium bromide and discussed the possible mechanisms from this point of view. We have found ZnCl2, MnCl2, AlCl 3 and CuCl to be active catalytic components and developed very efficient, cheap and fast methods for the preparation of alkyl adamantyl ketones. The procedure was also tested for the synthesis of other alkyl aryl ketones. Graphical Abstract.

Catalyst comprising a cyclic imide compound and process for producing organic compounds using the catalyst

A catalyst includes a cyclic imide compound having an N-substituted cyclic imide skeleton represented by following Formula (I): wherein X is an oxygen atom or a hydroxyl group, and having a solubility parameter of less than or equal to 26 [(MPa)?] as determined by Fedors method. The catalyst may further comprise a metallic compound. By allowing (A) a compound capable of forming a radical to react with (B) a radical scavenging compound in the presence of the catalyst, an addition or substitution reaction product between the compound (A) and the compound (B) or a derivative thereof can be obtained.

Adamantanemethanol derivatives and production processes thereof

An adamantanemethanol derivative of the invention is represented by the following formula (1), wherein Rais a hydrogen atom or a hydrocarbon group; Rbis a hydrocarbon group having a carbon atom, to which carbon atom at least one hydrogen atom is bonded, at a bonding site with the adjacent carbon atom; Rc, Rdand Reare each a hydrogen atom, a hydroxyl group which may be protected by a protective group or the like; provided that a hydroxyl group protected by a protective group or the like is bonded to at least one carbon atom constituting the adamantane skeleton when Rais a hydrogen atom or a methyl group and Rbis a methyl group; and at least one substituent, in addition to the HO—C(Ra)(Rb)— group indicated in the formula (1), is bonded to the adamantane ring when one of Raand Rbis a methyl group and the other is an ethyl group.

The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates

Solvolysis rates, alpha and beta deuterium isotope rate effects and product yields have been determined for some 1-(1-adamantyl) propyl sulfonate esters, 4, in some ethanol-water, trifluoroethanol-water and hexafluoroisopropyl alcohol-water mixtures. For comparison, similar measurements have been made for solvolysis of 2,2-dimethyl-3-pentyl sulfonates, 5. For the esters 5, the alpha-d and beta-d2 effects vary little with solvent in the ranges of 1.164-1.165 and 1.215-1.241, respectively, and only small yields of unrearranged products are formed; it is concluded that the mechanism involves rate determining formation of the secondary cation-ion pair followed by rapid rearrangement. For the adamantyl analogs, 4, the alpha-d effects vary in the different solvents from 1.162 to 1.213 and the beta-d2 effects vary from 1.339 to 1.649; significant yields of unrearranged and Wagner-Meerwein rearranged (ring expansion) products are formed. The steady state treatment, which had been used previously to fit the results for 1-(1-adamantyl)ethyl esters, was applied to the results for 4; a mechanism which involves partially reversible ionization to the intimate ion-pair followed by competing elimination and solvent separation, to give the substitution products, fits the results reasonably well.

Synthesis of 1-adamantyl and 1-adamantylmethyl alkyl ketones

The reaction of 1-adamantanecarboxylic and 1-adamantylacetic acids with Grignard reagents in the presence of cuprous chloride or iodide gave the corresponding ketones.

REACTION OF 1-ADAMANTANOL WITH α-OLEFINS IN TRIFLUOROACETIC ACID

In the reaction of 1-adamantanol with α-olefins (CH2=CHR) in the presence of trifluoroacetic acid the main reaction products are 1-(1-adamantyl)1-alkanols, and the side products are the isomeric alcohols and alkenyladamantanes.In the reaction of 1-adamantanol with 1,5-hexadiene selective reaction occurs between the initial alcohol and only one double bond of the diene; adamantylated hydrocarbons are mainly formed as a result of the reaction.The reaction of 1-adamantanol with α-olefins in trifluoroacetic acid can be used as a preparative method for the production of hydroxyalkyladamantanes.