1459-96-7

Basic information

• Product Name: dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
• Synonyms: dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;DiMethyl -bicyclo[2.2.2]octan-1,4-dicarboxylate;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid dimethyl ester;2,2-diMethylbicyclo[2.2.2]octane-1,4-dicarboxylate;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, 1,4-diMethyl ester;iMethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;1,4-dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;Dimethyl bioyclo[2.2.2]octane-1,4-dicarboxylate
• CAS NO: 1459-96-7
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.27
• Mol File: 1459-96-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 273.6 °C at 760 mmHg
• Flash Point: 126.968 °C
• Appearance: white crystal
• Density: 1.206 g/cm³
• Vapor Pressure: 0.00568mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate(1459-96-7)
• EPA Substance Registry System: dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate(1459-96-7)

Safety Data

• Hazardous Substances Data: 1459-96-7(Hazardous Substances Data)

Usage

Description

Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate is an organic compound characterized by its bicyclic structure and ester functional groups. It is a white crystalline solid that is soluble in organic solvents and has a molecular weight of approximately 222 g/mol. dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate is known for its unique chemical properties and potential applications in various industries.

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 
• 174685-35-9 dimethyl 1'H,4'H-dispiro[1,3-dithiolane-2,2'-bicyclo[2.2.2]octane-5',2''-[1,3]dithiolane]-1',4'-dicarboxylate 
• 94-60-0 dimethyl 1,4-cyclohexane dicarboxylate 
• 107-04-0 1-Bromo-2-chloroethane 
• 57293-62-6 dimethyl 1,4-dioxobicyclo<2.2.2>octane-2,5-dicarboxylate 
• 6289-46-9 dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate 
• 1659-95-6 dimethyl 1,3-cyclohexadiene-1,4-dicarboxylate 
• 100-21-0 terephthalic acid 
• 1659-96-7 1,4-dibromo-trans-cyclohexane-1,4-dicarboxylic acid dimethyl ester 
• 340023-18-9 cis/trans-1-(2-iodoethyl)-cyclohexane-1,4-dicarboxylic acid dimethyl ester 
• 619-81-8 cyclohexane-1,4-dicarboxylic acid 
• 67-56-1 methanol 
• 711-02-4 1,4-bicyclo[2.2.2]octanedicarboxylic acid 

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 
• 1403864-73-2 benzyl 4-hydroxybicyclo[2.2.2]octan-1-ylcarbamate 
• 105176-66-7 (4-aminobicyclo[2.2.2]octan-1-yl)methanol 
• 1333384-43-2 tert-butyl (4-(hydroxymethyl)bicyclo[2.2.2]octane-1-yl)carbamate 
• 1514592-12-1 N,N'-dibenzylbicyclo[2.2.2]octane-1,4-dicarboxamide 
• 1514592-15-4 N-((4-((benzylamino)methyl)bicyclo[2.2.2]octan-1-yl)methyl)(phenyl)methanamine 

Relevant articles and documents

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.

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.

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.

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.