1459-95-6

Usage

Uses

Used in Chemical Laboratories:
Dimethyl 1,3-adamantanedicarboxylate is used as a reactant in chemical laboratories for the synthesis of other chemicals. Its unique structure and properties make it a valuable component in various chemical reactions.
Used in Research:
In the field of research, Dimethyl 1,3-adamantanedicarboxylate is employed as a starting material or intermediate in the development of new chemical compounds. Its versatility in chemical reactions allows researchers to explore its potential applications in different areas of chemistry.
Used in Manufacturing Sector:
Dimethyl 1,3-adamantanedicarboxylate is utilized in the manufacturing sector, particularly for the production of various chemical products. Its role in the synthesis process is crucial for the creation of a wide range of compounds used in different industries.

InChI:InChI=1/C14H20O4/c1-17-11(15)13-4-9-3-10(5-13)7-14(6-9,8-13)12(16)18-2/h9-10H,3-8H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 281-23-2 adamantane 
• 67-56-1 methanol 
• 39269-10-8 adamantane-1,3-dicarboxylic acid 
• 768-90-1 1-Adamantyl bromide 
• 201230-82-2 carbon monoxide 
• 876-53-9 1,3-dibromoadamantane 

Downstream Products

• 101725-90-0 1,3-Adamantane bis(α,α-dimethylmethyl) diol 
• 17071-62-4 1,3-bis(2-hydroxymethyl)adamantane 

Relevant academic research and scientific papers

Synthesis and cytotoxicity of novel simplified eleutherobin analogues as potential antitumour agents

Mixed simplified structures containing the paclitaxel and eleutherobin pharmacophore moieties were analyzed using molecular docking techniques and synthesized based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds. The crucial role of substituents' stereochemistry in biological activity is discussed. At micromolar concentrations the selected analogues interfered with tubulin dynamics in vitro and in a living organism. Furthermore, new compounds were cytotoxic against human tumour cell lines. The simplified eleutherobin analogues may be considered as prototypes of a new class of antitumour agents.

Molecular tetrominoes: selective masking of the donor π-face to control the configuration of donor–acceptor complexes

Understanding the doping mechanism in organic semiconductors and generating molecular design rules to control the doping process are crucial for improving the performance of organic electronics. Even though controlling the location and orientation of the dopant along the semiconductor backbone is an important step in the doping mechanism, studies in this direction are scarce as it is a challenging task. To address this, herein, we incorporated π-face masked (strapped) units in 1,4-bis(phenylethynylene)benzene (donor) to control the acceptor (dopant) location along the trimer, donor–acceptor binding strength, and acceptor ionization. Two strapped trimers, PCP and CPC, are synthesized with control over the location of the strapped repeat unit in the trimer. The trimers are complexed with the 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) acceptor in solution. DFT calculations show that DDQ residing on the non-strapped repeat unit (the percentage of this configuration is at least ca. 73%) has the highest binding energy for both PCP and CPC. The percentage of dopant ionization is higher in the case of strapped trimers (PCP and CPC) compared to that of linear control trimers (PLP and LPL) and the completely non-strapped (PPP) trimer. The percentage of dopant ionization increased by 15 and 59% in the case of PCP and CPC respectively compared to that of PPP.

Facile synthesis and antimycobacterial activity of isoniazid, pyrazinamide and ciprofloxacin derivatives

Several rationally designed isoniazid (INH), pyrazinamide (PZA) and ciprofloxacin (CPF) derivatives were conveniently synthesized and evaluated in vitro against H37Rv Mycobacterium tuberculosis (M. tb) strain. CPF derivative 16 displayed a modest activity

Enhancing Insulated Conjugated Polymer Fluorescence Quenching by Incorporating Dithia[3.3]paracyclophanes

Insulated π-conjugated polymers exhibit enhanced chemical stability, photostability, fluorescence quantum yield, electroluminescence, solubility, and intrachain charge transport. However, insulated polymer fluorescence quenching by acceptor molecules is significantly hampered as the π-face is insulated. Photoinduced charge transfer is one of the key steps in amplified fluorescence quenching sensors and organic solar cells for charge generation. Inspired by the myelin sheath gaps in nerve cell axons, herein, we synthesized a series of insulated random copolymers of adamantanocyclophane with an increasing percentage of dithia[3.3]paracyclophane (PCP) from 5 to 30% to enhance the insulated polymer fluorescence quenching with acceptor molecules. As the percentage of the dithia[3.3]paracyclophane monomer increases, the copolymers showed an increase in absorption in the red region of the spectrum and also the copolymers' photoluminescence quantum yield reduced. The Stern-Volmer quenching constant of the 30% copolymer is ca. 4.5 times higher than that of the adamantanocyclophane homopolymer. A comparison with the control polymers indicated that the through-space-coupled interactions in PCP could be a plausible reason for the enhanced fluorescence quenching in copolymers in addition to the reduced steric hindrance by PCP. The developed copolymers combine the advantages of polymer insulation without significantly sacrificing the photoinduced charge transfer, which will help further their applicability as amplified fluorescence quenching sensors and in organic solar cells.

Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation

Histidine (His) carries a unique heteroaromatic imidazole side chain and plays irreplaceable functional roles in peptides and proteins. Existing strategies for site-selective histidine modification predominantly rely on the N-substitution reactions of the moderately nucleophilic imidazole group, which inherently suffers from the interferences from lysine and cysteine residues. Chemoselective modification of histidine remains one of the most difficult challenges in peptide chemistry. Herein, we report peptide modification via radical-mediated chemoselective C-H alkylation of histidine using C4-alkyl-1,4-dihydropyridine (DHP) reagents under visible-light-promoted conditions. The method exploits the electrophilic reactivity of the imidazole ring via a Minisci-type reaction pathway. This method exhibits an exceptionally broad scope for both peptides and DHP alkylation reagents. Its utility has been demonstrated in a series of important peptide drugs, complex natural products, and a small protein. Distinct from N-substitution reactions, the unsubstituted nitrogen groups of the modified imidazole ring are conserved in the C-H alkylated products.

The first one-pot synthesis of 1,3-dicarbonyl adamantanes from 1-bromoadamantanes

Treatment of 1-bromoadamantane and 1-bromo-3,5-dimethyladamantane with CBr4·2AlBr3 under carbon monoxide atmosphere followed by quenching with nucleophiles affords 1,3-dicarbonyl adamantanes.

Adamantane derivatives and resin compositions using the same as raw material

The adamantane derivatives of the present invention which are represented by the general formula (1): wherein X is a hydrogen atom, alkyl, halogen-containing alkyl, halogen, or hydroxyl-, halogen-, nitrile- or ether-containing hydrocarbyl, and a plurality of X groups, if any, may be the same or different from each other; n1 is an integer of 1 to 14; R1 to R4 may be the same or different from each other and are independently alkyl or halogen-containing alkyl; and Y1 and Y2 may be the same or different from each other and are independently a hydrogen atom or a group represented by the general formula (2): wherein R5 to R7 may be the same or different from each other and are independently a hydrogen atom, alkyl, halogen or halogen-containing alkyl, are excellent in optical properties, heat resistance and acid-dissociating property, and useful as crosslinking-type resins, optical materials such as optical fibers, light wave guides, optical disk substrates and photoresists as well as raw materials thereof, intermediate products of medicines or agricultural chemicals, and various other industrial products.

NITRATION OR CARBOXYLATION CATALYSTS

In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the following formula (1): ???wherein R1and R2represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a cycloalkyl group, and R1and R2may bond together to form a double bond, or an aromatic or non-aromatic ring, and Y is an O or OH, and n denotes 1 to 3;, a substrate is allowed to contact with at least one reactant selected from (i) a nitrogen oxide and (ii) a mixture of carbon monoxide and oxygen to be introduced with at least one functional group selected from a nitro group and a carboxyl group. The nitrogen oxide includes, for example, a compound represented by the formula NxOy(e.g., N2O3, NO2). The substrate includes, for example, a compound having a methine carbon atom (e.g., adamantane), a compound having a methyl group or a methylene group at an adjacent moiety of an aromatic ring. According to such reaction, the substrate can be efficiently nitrated or carboxylated even in a mild or moderate condition.