1459-96-7

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate is used as a key intermediate in the synthesis of cycloalkanecarboxamides and related compounds. These compounds serve as modulators of the integrated stress pathway, which is a cellular response mechanism to various stressors, including endoplasmic reticulum stress, oxidative stress, and nutrient deprivation. By modulating this pathway, these compounds have potential therapeutic applications in the treatment of various diseases and conditions, such as neurodegenerative disorders, metabolic diseases, and certain types of cancer.
Used in Chemical Synthesis:
In addition to its pharmaceutical applications, dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate can also be used as a building block in the synthesis of various organic compounds. Its unique bicyclic structure and ester functional groups make it a valuable starting material for the development of new molecules with potential applications in various fields, such as materials science, agrochemistry, and specialty chemicals.

InChI:InChI=1/C12H18O4/c1-15-9(13)11-3-6-12(7-4-11,8-5-11)10(14)16-2/h3-8H2,1-2H3

Upstream product

• 1659-67-2 dimethyl bicyclo[2.2.2]oct-2-ene-1,4-dicarboxylate 
• 106004-06-2 dimethyl 1-(2'-chloroethyl)cyclohexane-1,4-dicarboxylate 
• 94-60-0 dimethyl 1,4-cyclohexane dicarboxylate 
• 107-04-0 1-Bromo-2-chloroethane 
• 67-56-1 methanol 
• 711-02-4 1,4-bicyclo[2.2.2]octanedicarboxylic acid 
• 62476-38-4 (1R,3R,6R,8R)-Tricyclo[4.2.0.0^3,8]octane-3,6-dicarboxylic acid dimethyl ester 
• 29412-62-2 dimethyl pentacyclo[4.2.0.0.^2,50.^3,80^4,7]octane-1,4-dicarboxylate 
• 54774-94-6 4-acetoxybicyclo<2.2.2>octan-1-ol 
• 10364-35-9 1,4-Diacetoxybicyclo<2.2.2>octane 
• 4982-20-1 1,4-dimethylidenecyclohexane 
• 1194-44-1 1,4-dihydroxybicyclo[2.2.2]octane 
• 619-81-8 cyclohexane-1,4-dicarboxylic acid 
• 340023-18-9 cis/trans-1-(2-iodoethyl)-cyclohexane-1,4-dicarboxylic acid dimethyl ester 

Downstream Products

• 18720-35-9 bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester 
• 711-02-4 1,4-bicyclo[2.2.2]octanedicarboxylic acid 
• 94994-15-7 4-hydroxymethyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester 
• 94994-25-9 4-carbomethoxybicyclo<2.2.2>octane-1-carboxaldehyde 
• 23062-52-4 methyl 4-phenylbicyclo<2.2.2>octane-1-carboxylate 
• 23042-19-5 methyl 4-(4-nitrophenyl)bicyclo[2.2.2]octane-1-carboxylate 
• 1127-13-5 4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid 
• 23062-53-5 methyl 4-hydroxybicyclo<2.2.2>octane-1-carboxylate 
• 826-45-9 Bicyclo<2.2.2>octane-1,4-dimethanol 
• 711-02-4 bicyclo<2.2.2>octane-1,4-dicarboxylic acid 
• 78385-84-9 4-fluorobicyclo<2.2.2>octane-1-carboxylic acid 

Relevant academic research and scientific papers

Rodlike molecules by Kolbe electrolysis

A new short and simple pathway to rigid, rod-shaped hydrocarbon skeletons, in particular of the oligo-bicyclo[2.2.2]octane type, is described. The key step consists of an electrochemical C-C bond coupling reaction between bridgehead positions of bi- and tricyclic carboxylic acids. Functional groups can be retained, they influence the yield of the C-C bond connection. In this way, otherwise difficult or laborious syntheses are shortened, and rigid, non-collapsable nano size spacer units are easily available. The optimized electrochemical procedures are described in detail.

Design and synthesis of novel 19F-amino acid: A promising 19F NMR label for peptide studies

Novel aliphatic 19F-substituted amino acid was designed as a 19F NMR label for peptide studies. The synthesis was performed in 11 steps and 9% overall yield from a commercially available starting material. The key transformation was a decarboxylative fluorination of an aliphatic carboxylic acid with XeF2 in C6F6.

Unique gas and hydrocarbon adsorption in a highly porous metal-organic framework made of extended aliphatic ligands

High and unique gas and hydrocarbon adsorption in a highly stable guest-free microporous metal-organic framework constructed on rigid aliphatic ligands, H2bodc and ted, is reported in this work. The Royal Society of Chemistry.

SYNTHESIS OF BICYCLO[2.2.2]OCTANE DERIVATIVES

Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives.

Bicyclo [2.2.2] octane - 1, 4 - dicarboxylic acid mono methyl ester synthesis method

The invention relates to a synthetic method of an organic compound. The synthetic method of bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl easter is as follows: firstly, adopting sodium hydride, DMSS and 1,2-dibromoethane to synthesize the intermediate I; secondly, adopting the intermediate I, sodium acetate, ammourea hydrochloride and alcohol to synthesize semicarbazon; thirdly, adopting potassium hydroxide, diethylene glycol and semicarbazon to synthesize target diacid; fourthly, adopting target diacid, thionyl chloride and methanol to synthesize target diester; and fifthly, adopting target diester, potassium hydroxide and 95% of methanol water solution to synthesize the target product monoester. The invention has reasonable synthetic process route, mild process conditions, environment friendly, easy operation, low raw material cost, high product yield and excellent purity, and is applicable to industrial production and satisfies the application requirement of each industry.

Tuning Singlet Fission in π-Bridge-π Chromophores

We have designed a series of pentacene dimers separated by homoconjugated or nonconjugated bridges that exhibit fast and efficient intramolecular singlet exciton fission (iSF). These materials are distinctive among reported iSF compounds because they exist in the unexplored regime of close spatial proximity but weak electronic coupling between the singlet exciton and triplet pair states. Using transient absorption spectroscopy to investigate photophysics in these molecules, we find that homoconjugated dimers display desirable excited-state dynamics, with significantly reduced recombination rates as compared to conjugated dimers with similar singlet fission rates. In addition, unlike conjugated dimers, the time constants for singlet fission are relatively insensitive to the interplanar angle between chromophores, since rotation about σ bonds negligibly affects the orbital overlap within the π-bonding network. In the nonconjugated dimer, where the iSF occurs with a time constant >10 ns, comparable to the fluorescence lifetime, we used electron spin resonance spectroscopy to unequivocally establish the formation of triplet-triplet multiexcitons and uncoupled triplet excitons through singlet fission. Together, these studies enable us to articulate the role of the conjugation motif in iSF.

SPIRO AZETIDINE ISOXAZOLE DERIVATIVES AND THEIR USE AS SSTR5 ANTAGONISTS

Provided is a compound represented by the following formula (1) or a salt thereof, which has an SSTR5 antagonistic action: wherein each symbol has the same definition as in the specification.

Discovery of functionalized bisimidazoles bearing cyclic aliphatic-phenyl motifs as HCV NS5A inhibitors

This Letter describes the discovery of a number of functionalized bisimidazoles bearing a cyclohexylphenyl, piperidylphenyl, or bicyclo[2,2,2]octylphenyl motif as HCV NS5A inhibitors. Compounds 2c, 4b and 6 have demonstrated low single-digit nM potency in gt-1a replicon and double-digit pM potency in gt-1b replicon, respectively. Moreover, both 4b and 6 have, respectively, exhibited good oral bioavailability in rats with a favorable liver/plasma ratio of the drug concentration.

BRIDGED BICYCLIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Novel bridged bicyclic compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.

SUBSTITUTED DIAMINOCARBOXAMIDE AND DIAMINOCARBONITRILE PYRIMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH

Provided herein are Diaminopyrimidine Compounds having the following structures: wherein R1, R2, R3, and R4 are as defined herein, compositions comprising an effective amount of a Diaminopyrimidine Compound, and methods for treating or preventing liver fibrotic disorders or a condition treatable or preventable by inhibition of a JNK pathway.