37567-78-5

Basic information

• Product Name: 1 5-DIMETHOXY-1 4-CYCLOHEXADIENE
• Synonyms: 1,5-diMethoxycyclohexa-1,4-diene;1,4-Cyclohexadiene, 1,5-Dimethoxy
• CAS NO: 37567-78-5
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.18
• Product Categories: Enol Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 37567-78-5.mol

Chemical Properties

• Boiling Point: 45-52 °C0.5 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: /
• Density: 1.020 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0511mmHg at 25°C
• Refractive Index: n20/D 1.4910(lit.)
• CAS DataBase Reference: 1 5-DIMETHOXY-1 4-CYCLOHEXADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1 5-DIMETHOXY-1 4-CYCLOHEXADIENE(37567-78-5)
• EPA Substance Registry System: 1 5-DIMETHOXY-1 4-CYCLOHEXADIENE(37567-78-5)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 2
• Hazardous Substances Data: 37567-78-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,5-Dimethoxy-1,4-cyclohexadiene is used as a building block in organic synthesis for the production of a wide range of pharmaceuticals and organic compounds. Its reactivity and ability to form different types of chemical bonds make it a valuable component in creating diverse products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1,5-Dimethoxy-1,4-cyclohexadiene is used as an intermediate for the synthesis of various drugs. Its unique structure and bonding capabilities allow for the development of new and innovative medications to address a variety of health concerns.
Used in Chemical Industry:
1,5-Dimethoxy-1,4-cyclohexadiene is also utilized in the chemical industry as an important intermediate for the production of a broad spectrum of products. Its versatility in forming chemical bonds contributes to the creation of numerous compounds used in various applications, from materials science to specialty chemicals.

InChI:InChI=1/C8H12O2/c1-9-7-4-3-5-8(6-7)10-2/h4-5H,3,6H2,1-2H3

Upstream product

• 634-36-6 1,2,3-trimethoxybenzene 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 151-10-0 1,3-Dimethoxybenzene 

Downstream Products

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 137265-65-7 3-(4'-Chlorobutyl)-2,4-dimethoxycyclohexa-1,4-diene 
• 54117-99-6 3-ethyl-2,4-dimethoxy-1,4-cyclohexadiene 
• 25435-93-2 1,5-dimethoxy-3-methylcyclohexa-1,4-diene 
• 33561-96-5 1,3-dimethoxy-2-methylcyclohexa-1,3-diene 
• 931-57-7 1-methoxy-cyclohex-1-ene 
• 504-02-9 1,3-cylohexanedione 
• 3401-01-2 2-isopropyl-cyclohexane-1,3-dione 
• 160537-93-9 3-(isobutyloxy)-2-isopropyl-2-cyclohexen-1-one 
• 1032475-83-4 C₁₅H₂₄O₂Si 
• 1609087-28-6 ethyl 2-[(2S,4S)-2,4-bis(tert-butyldimethylsilyloxy)heptyl]-4,6-dimethoxybenzoate 
• 1609087-36-6 ethyl 2-[(2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)heptyl]-4,6-dimethoxybenzoate 
• 81722-07-8 ethyl 2,4-dimethoxybenzoate 
• 93621-14-8 1-methoxy-2,3-dibenzoylbicyclo<2.2.2>oct-2-en-5-one 

Relevant articles and documents

Enantio- And Diastereoselective Construction of Contiguous Tetrasubstituted Chiral Carbons in Organocatalytic Oxadecalin Synthesis

The organocatalytic enantio- and diastereoselective cycloetherification of 1,3-cyclohexanedione-bearing enones involving the in situ generation of chiral cyanohydrins was developed. This transformation offers the first catalytic asymmetric approach to oxa

Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry

Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal-type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings.

Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones

A single-pot Cu-catalyzed enantio- and diastereoselective tandem hydroboration/borylative cyclization of alkynes with ketones for the synthesis of carbocycles is reported. The reaction proceeds via desymmetrization and generates four contiguous stereocent

FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers

Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6-tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ-terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).

Asymmetric Synthesis of Carbocyclic Propellanes

A modular synthesis of functionalized carbocyclic propellanes was developed. Formation of the first of two quaternary bridgehead centers has been achieved by desymmetrization of prostereogenic ketones by either Hajos-Parrish-Eder-Sauer-Wiechert-type processes or Werner’s catalytic asymmetric Wittig reaction. The obtained bicyclic enones were subjected to conjugate additions upon which the remaining ring was formed by olefin metathesis. All bridges are amenable to further derivatization, which renders those compounds useful as central units in fragment-based drug discovery or as ligand scaffolds.

Studies towards the total synthesis of cruentaren A and B: Stereoselective synthesis of fragments C1-C11, C12-C22 and C23-C28

A convergent and stereoselective approach for the synthesis of C1-C11, C12-C22, and C23-C28 fragments of cytotoxic natural products cruentaren A and B are accomplished. Highlights of the strategy include a Sharpless epoxidation followed by a regioselective opening of epoxide to generate anti and syn-stereochemistry at C9-C10 and C15-C16, an Alder-Rickert reaction between a 1,5-dimethoxy-1,4-cyclohexadiene and dienophile to construct the aromatic ring, and a lithium-mediated aldol reaction to install the C17-C18 anti-stereochemistry. The synthesis of C1-C11 and C12-C22 fragments proceed with a longest linear sequence of 10 and 17 steps from commercially available 2-butyne-1,4-diol and cis-2-butene-1,4-diol respectively.

Enantioselective total synthesis of hyperforin

A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3

An efficient formal total synthesis of cladosporin

A highly diasteroselective and efficient approach for the formal total synthesis of cladosporin is described. Cross-metathesis, iodocyclization to construct the trans-2,6-disubstituted dihydropyran ring system, and an Alder-Rickert reaction to form the ar

The stereoselective total synthesis of isocladosorpin

A highly stereoselective total synthesis of isocladosorpin is described. The key steps involved in this synthesis are oxa-Michael reaction, asymmetric propargylation, and Alder-Rickerts reaction.

Total synthesis of 7-desmethoxyfusarentin and its methyl ether

A concise total synthesis of 7-desmethoxyfusarentin and its methyl ether has been accomplished involving a sequence of reactions such as Prins cyclization, ring opening of tetrahydropyran ring and Alder-Rickerts reaction as key steps. This is the first report on the construction of anti-1,3-diol unit of 7-desmethoxyfusarentin by means of Prins cyclization.