50874-38-9

Usage

Tetrachloro

Four chlorine atoms

Dimethoxy

Two methoxy groups

Tetrahydro

Four hydrogen atoms added to a hydrocarbon

Methanonaphthalene

A naphthalene derivative with a modified structure

Dione

A carbonyl group (C=O) attached to two adjacent carbon atoms

Structure

A complex structure with a tetrahydro-1,4-methanonaphthalene core, four chlorine atoms, and two methoxy groups

Physical Properties

Likely a solid at room temperature due to the presence of multiple chlorine and methoxy groups
High molecular weight and complexity

Chemical Properties

Potentially reactive due to the presence of multiple functional groups
May be sensitive to heat, light, or moisture

Hazards

Potentially toxic due to the presence of multiple chlorine and methoxy groups
May be hazardous if inhaled, ingested, or absorbed through the skin

Uses

Limited due to its complex and potentially dangerous nature

Handling Precautions

Use appropriate personal protective equipment (PPE) when handling
Store in a cool, dry, and well-ventilated area
Avoid contact with heat, light, or moisture
Dispose of according to local regulations and guidelines

Environmental Impact

Potentially harmful to the environment if released in large quantities or improperly disposed of

Upstream product

• 2207-27-4 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene 
• 106-51-4 p-benzoquinone 
• 77-47-4 hexachlorocyclopentadiene 

Downstream Products

• 50874-39-0 4,4-dimethoxy-2,3,5,6-tetrachloropentacyclo<5.4.0.0^2.6.0^3.10.0^5.9>undecane-8.11-dione 
• 77861-04-2 C₂₀H₂₃IO₅S 
• 77867-77-7 C₂₇H₃₀O₈S₂ 

Relevant academic research and scientific papers

Benzoannulation of quinones by a cycloaddition-fragmentation approach. A simple synthesis of methoxycarbonyl-substituted polyacenoquinones

The cycloadducts 2A-5A obtained from the Diels-Alder cycloadditions of 1,2,3,4-tetrachloro-4,5-dimethoxycyclopentadiene (1) with p-benzoquinone (2), 1,4-naphthoquinone (3), 1,4-anthraquinone (4), and 2,3-dicyano-1,4-benzoquinone (5) were subjected to the reaction with triethylamine in dichloromethane at room temperature. Cycloadducts 2A and 5A enolized to give the corresponding hydroquinones 2B and 5B, which were oxidized with DDQ to afford naphthoquinone ester 2D and anthraquinone ester 5D, respectively. In the cases of cycloadducts 3A and 4A, the enolization occurred concurrently with oxidation and fragmentation to produce directly the polyacenoquinone esters 3D and 4D, respectively. Under the same reaction condition, the unsymmetrical cycloadduct 6A derived from naphthoquinone ester 2D and 1 yielded isomeric polyacenoquinone esters 6Da and 6Db in a ratio of about 8:1.

An unusual fragmentation reaction of substituted 2,3-norbornylhydroquinone with CAN: synthesis of 1,4-naphthoquinone

When substituted 2,3-norbornylhydroquinone is treated with CAN with or without water, an unusual fragmentation-aromatization reaction occurs which leads to a substituted 1,4-naphthoquinone instead of the desired substituted 2,3-norbornylbenzoquinone.

Quinoxaline-annelated Z-shaped quadruple-bridged orthocyclophanes: Synthesis and crystal structures

A three-step synthesis of nineteen Z-shaped quadruple-bridged [6,6] and [6,4]orthocyclophanes comprising two quinoxaline-based sidewalls are described. The synthesis began from the bis-Diels-Alder adducts B1-B3 followed by ruthenium-promoted oxidation of dichloroetheno-bridges in the adducts to generate a bis-α-diketones, which were then condensed with various arene-1,2-diamines (9a-g) to construct sidewalls (phane parts) of Z-shaped quadruple-bridged orthocyclophanes D1-3, D2g, and D3g. Single-crystal structures of six orthocyclophanes (D1a, D2a, D2f, D3f, D2g-α, and D3g-α) were obtained and revealed that the CAr-H?π and π?π stacking interactions between N-containing arene rings are the major driving force for molecular assembly and crystal packing, in addition to the interactions involving the polar OCH3 groups and the solvate molecules.

Polycyclitols - Novel conduritol and carbasugar hybrids as new glycosidase inhibitors

A family of novel carbasugar analogues (bicyclitols) based on cis-hydrindane and cis-decalin frameworks has been conceptualized. These novel entities can be regarded as conduritol and carbasugar hybrids. Syntheses of these polyhydroxylated entities have been achieved in stereo- and regioselective manners, starting from the readily available Diels-Alder adducts of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and appropriate dienophiles like cyclopentadiene or p-benzoquinone, that embody a masked 7-ketonorbornenone moiety. Thermally induced chelotropic elimination of CO from the appropriately functionalized 7-ketonorbornenone derivatives to deliver annulated bicyclic 1,3-cyclohexadiene derivatives was the key step in this synthetic endeavor. Further oxy-functionalization of the 1,3-cyclohexadiene moiety delivered the targeted polycyclitols. A preliminary investigation of the glycosidase inhibitory potency of these bicyclitols, identified compounds 18 and 54 as potent and selective inhibitors of α-glucosidase (yeast).

Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.

Catalytic Enantioselective Desymmetrization of Norbornenoquinones via C(sp2)-H Alkylation

The enantioselective Diels-Alder (DA) reaction with monosubstituted p-benzoquinones is an unmet challenge. A new approach for the enantioselective synthesis of monosubstituted quinone-DA adducts is presented based on C(sp2)-H alkylative desymmetrization of meso-DA adducts. Catalyzed by a tertiary amino-thiourea derivative, this reaction utilizes nitroalkanes as the alkylating agents and generates densely functionalized products bearing at least four contiguous stereogenic centers remote from the reaction site with excellent enantioselectivities.