28495-21-8

Basic information

• Product Name: 1,4-Cyclohexadiene, 1,5-dimethoxy-3-methyl-
• CAS NO: 28495-21-8
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• Mol File: 28495-21-8.mol

Chemical Properties

• CAS DataBase Reference: 1,4-Cyclohexadiene, 1,5-dimethoxy-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Cyclohexadiene, 1,5-dimethoxy-3-methyl-(28495-21-8)
• EPA Substance Registry System: 1,4-Cyclohexadiene, 1,5-dimethoxy-3-methyl-(28495-21-8)

Safety Data

• Hazardous Substances Data: 28495-21-8(Hazardous Substances Data)

Usage

Structure

A six-membered ring hydrocarbon with two double bonds, two methoxy groups, and a methyl group.

Derivative of

Cyclohexadiene

Double bonds

Conjugated diene system

Methoxy groups

Two -OCH3 groups

Methyl group

One -CH3 group

Industrial applications

As a building block for other organic compounds

Pharmaceutical applications

In chemical synthesis

Safety precautions

Proper handling and safety measures should be observed to prevent health or environmental hazards.

Upstream product

• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 6443-69-2 3,4,5-trimethoxytoluene 

Downstream Products

• 26166-39-2 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2Z,4E)-3-methyl-5-((1S,2S,6S)-1,2,6-trimethyl-3-oxo-cyclohexyl)-penta-2,4-dienyl]-benzaldehyde 
• 13365-08-7 2,4-dibromo-1,5-dimethoxy-3-methylbenzene 
• 54118-01-3 1,5-dimethoxy-3,6-dimethyl-1,4-cyclohexadiene 
• 1451073-94-1 C₁₆H₁₉NO₃ 
• 1451077-72-7 C₁₆H₁₉NO₃ 
• 1451077-61-4 C₁₇H₂₁NO₂ 
• 1451077-60-3 C₁₃H₁₅NO₂ 
• 70150-66-2 5-methyl-3-hydroxycyclohex-2-enone 
• 61621-47-4 2,5-dimethyl-1,3-cyclohexanedione 
• 99477-61-9 (2'E,6'E,1''S,4''S)-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione 
• 99477-61-9 (2'E,6'E,1''R,4''R)-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione 
• 85785-76-8 (2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione 
• 85785-76-8 (+/-)-(2'Z,4'E)-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione 
• 94286-84-7 4,6-dichloro-2-farnesyl-5-methyl-1,3-cyclohexanedione 

Relevant articles and documents

Synthetic studies towards the Lycopodium alkaloid paniculatine

Two bridging tetracyclic products have been observed while attempting to construct the final C-ring of the Lycopodium alkaloid, paniculatine, by an intramolecular addition of enolates to unactivated N-alkyl pyridinium salts. The Royal Society of Chemistry 2013.

Total synthesis of (+)-nankakurines A and B and (±)-5-epi- nankakurine A

The first total syntheses of the Lycopodium alkaloids (+)-nankakurine A (2), (+)-nankakurine B (3), and the originally purported structure 1 of nankakurine A were accomplished. The syntheses of 2 and 3 feature a demanding intramolecular azomethine imine cycloaddition as the key step for generating the octahydro-3,5-ethanoquinoline moiety and installing the correct relative configuration at the spiropiperidine ring juncture. The cyclization precursor was prepared from octahydronaphthalene ketone 50, which was assembled from enone (+)-9 and diene 48 by a cationic Diels-Alder reaction. The Diels-Alder reactants were synthesized from 5-hexyn-1-ol (16) and (+)-pulegone (49), respectively. The tetracyclic ring system of 1 was generated using an unprecedented nitrogen-terminated aza-Prins cyclization cascade. The enantioselective total syntheses of (+)-nankakurine A (2) and (+)-nankakurine B (3) establish the relative and absolute configuration of these alkaloids and are sufficiently concise that substantial quantities of 2 and 3 were prepared for biological studies. (+)-Nankakurine A and (+)-nankakurine B showed no effect on neurite outgrowth in rat hippocampal H-19 cells over a concentration range of 0.3-10 μM.

Synthesis of chiloglottones - Semiochemicals from sexually deceptive orchids and their pollinators

A five-step synthesis of monoalkyl- and 2,5-dialkyl-1,3-cyclohexanediones (1) is described via a sequence involving sequential Birch reductions and alkylations from the readily accessible and inexpensive starting material, 3,5-dimethoxybenzoic acid. Two approaches were considered in which alkylation at C-2 occurs either prior or subsequent to the proposed reduction. The successful route, in which Birch reduction of a 3-alkyl resorcinol derivative (3) precedes alkylation was applied in the synthesis of chiloglottone 1 (1dc), in 58% overall yield. Chiloglottone 1 is a member of a new class of natural products, representing a known sex pheromone of the thynnine wasp Neozeleboria cryptoides and pollinator attractant in the Australian sexually deceptive orchid genus Chiloglottis. The synthetic homologues were assessed for their biological activity via electroantennographic detection.

Synthesis of substituted quinazolines

A novel and flexible synthetic route is described for the synthesis of 5,6,8-alkyl-7-methoxy-2-aminoquinazolines using dihydrobenzenes as key intermediates.

Synthesis of 4,4-Disubstituted Cyclohexenones. Part 2. Cycloaddition of 2-Chloroacrylonitrile to 5-Substituted 1,3-Dimethoxycyclohexa-1,4-dienes

The cycloaddition of 2-chloroacrylonitrile to 1,3-dimethoxycyclohexadienes (3; R1=OMe, R2=H), derived by in situ conjugation of the Birch reduction products (12) produced from aromatic precursors (11) gave after acid work-up mainly bicyclooctanone

A GENERAL SYNTHETIC METHOD FOR PRENYLATED PHENOLS OF MICROBIAL ORIGIN

Prenylated phenols with a fully substituted benzene ring, such as colletochlorins A and B, were synthesized by first prenylating 1,5-dimethoxy-3-methyl-1,4-cyclohexadiene and then effecting the aromatization of the prenylated product.