134962-99-5

Basic information

• Product Name: 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol
• Synonyms: 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol
• CAS NO: 134962-99-5
• Molecular Weight: 302.457
• Mol File: 134962-99-5.mol

Chemical Properties

• CAS DataBase Reference: 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol(134962-99-5)
• EPA Substance Registry System: 4-Methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,6-dihydro-2H-pyran-2-ol(134962-99-5)

Safety Data

• Hazardous Substances Data: 134962-99-5(Hazardous Substances Data)

Upstream product

• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 58274-64-9 (E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane 
• 5560-99-6 (2X,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienal 

Downstream Products

• 116-31-4 all-trans-Retinal 
• 116-31-4 vitamin A aldehyde 

Relevant articles and documents

Prenylation reaction performed with catalytically generated potassium prenal dienolate

A new prenylation method based on the reaction of catalytically generated potassium dienolate of prenal with α,β-unsaturated aldehydes is described. The reaction is highly regioselective, via a γ-1,2-addition, and provides an efficient route to retinal.

Regioselective addition of the prenal potassium dienolate onto α,β- unsaturated aldehydes. A short access to polyenaldehydes

The potassium dienolate of prenal obtained by treatment of the corresponding dienoxysilane with tBuOK was reacted with enaldehydes. In all cases a γ-specific reaction occurs. According to the reaction conditions a γ ;1,2 or a γ ;1,4 coupled product was selectively obtained with enals. The γ;1,2 reaction provided an efficient prenylation procedure. A short two- step synthesis of retinal is described.

A new prenylation method using the lithium enolate of prenal. Reaction with polyunsaturated aldehydes. A short access to retinal

The enolate of prenal 1 prepared from the corresponding silyl enol ether 2 or enol acetate 3 led to a γ-regiospecific reaction with polyunsaturated aldehydes 4 yielding dihydropyrans 5 leading after hydrolysis to polyenals 7. This process allows the introduction of the isoprenyl skeleton. A synthesis of retinal, from β-ionylidenacetaldehyde is reported.