100572-82-5

Basic information

• Product Name: 1-(1,5-dimethyl-4-hexenyl)-4-methoxy-1,4-cyclohexadiene
• Synonyms: 1-(1,5-dimethyl-4-hexenyl)-4-methoxy-1,4-cyclohexadiene
• CAS NO: 100572-82-5
• Molecular Weight: 220.355
• Mol File: 100572-82-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(1,5-dimethyl-4-hexenyl)-4-methoxy-1,4-cyclohexadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1,5-dimethyl-4-hexenyl)-4-methoxy-1,4-cyclohexadiene(100572-82-5)
• EPA Substance Registry System: 1-(1,5-dimethyl-4-hexenyl)-4-methoxy-1,4-cyclohexadiene(100572-82-5)

Safety Data

• Hazardous Substances Data: 100572-82-5(Hazardous Substances Data)

Upstream product

• 100572-91-6 (E,Z)-4-(1,5-Dimethyl-1,4-hexadienyl)-1-methoxybenzol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 16647-04-4 6-methyl-3,5-heptadien-2-one 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 68178-48-3 2-(4-Methoxyphenyl)-6-methyl-5-hepten-2-ol 

Downstream Products

• 1723-81-5 zingiberenol 
• 1723-81-5 cis-4-(6-methyl-5-hepten-2-yl)-1-methyl-2-cyclohexen-1-ol 
• 20489-36-5 [S-(R*,S*)]-3-(1,5-dimethyl-4-hexenyl)-6-methylene cyclohexene 
• 100572-83-6 4-(1,5-dimethyl-4-hexenyl)-3-cyclohexen-1-one 
• 1723-80-4 4-(6-methyl-5-hepten-2-yl)-2-cyclohexen-1-one 

Relevant articles and documents

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Efficient Syntheses of β-Sesquiphellandrene and Zingiberenol Employing a Tandem Arylation-Multistep Reduction-Hydrolysis Sequence

The title sesquiterpenes are synthesized in one step from the common intermediate 4-(6-methyl-5-hepten-2-yl)-2-cyclohexen-1-one, which is prepared using a one-pot tandem arylation-multistep reduction-hydrolysis sequence.

Selective Synthesis of Either Complex Aromatic Alkenes or (1,4-Cyclohexadienyl)alkenes by Tandem Arylation-Multistep Reduction of α,β,γ,δ-Unsaturated Ketones

(1,4-Cyclohexadienyl)alkenes are conveniently prepared in excellent isolated yields from α,β,γ,δ-unsaturated ketones by tandem alkylation-multistep reductions.By this one-pot procedure, complex diene benzyl alkoxides, generated in situ by arylation of α,β,γ,δ-unsaturated ketones with organolithium reagents, are reduced by a multistep reduction process in lithium-ammonia-ethanol to the corresponding (1,4-cyclohexadienyl)alkenes.Examples include the synthesis of 2-methyl-6-(1,4-cyclohexadien-1-yl)-2-heptene (7a), (+/-)-β-curcumene (7b), 2-methyl-6-(4-methoxy-1,4-cyclohe xadien-1-yl)-2-heptene (7c), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-(1,4-cyclohexadien-1-yl)butane (9a), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-(4-methyl-1,4-cyclohexadien-1-yl)butane (9b), and 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-(4-methoxy-1,4-cyclohexadien-1-yl)butane (9c) using phenyllithium, p-tolyllithium, and p-methoxyphenyllithium with 6-methyl-3,5-heptadien-2-one (1) and β-ionone (2), respectively.In contrast, use of the corresponding Grignard reagents prepared by the Rieke procedure results in the selective synthesis of the corresponding aromatic alkene.Examples include the synthesis of 2-methyl-6-phenyl-2-heptene (8a), (+/-)-α-curcumene (8b), 2-methyl-6-(p-methoxyphenyl)-2-heptene (8c), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-phenylbutane (10a), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-(4-tolyl)butane (10b), and 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-(p-methoxyphenyl)butane (10c) using phenylmagnesium bromide, p-tolylmagnesium bromide, and p-methoxyphenylmagnesium bromide with 6-methyl-3,5-heptadien-2-one (1) and β-ionone (2), respectively.The latter series of results suggest that some species, present in the Grignard sequence, is preventing the 1,4-reduction (Birch reduction) of the aromatic ring.