92464-72-7

Upstream product

• 76-83-5 trityl chloride 
• 106-24-1 Geraniol 
• 106-25-2 Nerol 
• 92464-82-9 (2E)-3,7-dimethyl-1-triphenylmethoxy-2,6-octadiene 

Downstream Products

• 37715-34-7 1-Trityloxy-6,7-dihydroxy-3,7-dimethyloct-2-en 
• 121952-87-2 (2E,6E)-3,7-dimethyl-1-triphenylmethoxy-2,6-nonadiene 
• 121952-89-4 3,7-dimethyl-2,6-nonadienal 
• 33431-27-5 6-Trityloxy-4-methylhex-4-ensaeure 
• 33431-26-4 6-Trityloxy-4-methylhex-4-enal 
• 53585-95-8 methyl (E)-6-hydroxy-4-methylhex-4-enoate 

Relevant academic research and scientific papers

THE PHOTOCHEMISTRY OF METHYL GERANATE, A MODEL CHROMOPHORE FOR INSECT JUVENILE HORMONE ANALOGS

The irradiation of methyl geranate (3) in ether using 254 nm lamps produces methyl 5-methyl-2-isopropenyl-4-hexenoate (13), 1,6,6-trimethyl-endo-5-carbomethoxybicyclo-hexane (11), methyl 2-isopropenyl-5-methylcyclopentanecarboxylate (12) and methyl (3Z)-3,7-dimethyl-3,6-octadienoate (14).Photolysis run in water or in ether in the presence of base generates two additional dienes: methyl 3-methylene-7-methyl-6-octaenoate (16) and methyl (3E)-3,7-dimethyl-3,6-octadienoate (17).The photolysis of methyl (2E, 6E)-3,7-dimethyl-2,6-nonadienoate (4a) in ether procedures all Z/E isomers, 4a - 4d.

1-Bromo-2-ethoxycyclolithium: A Synthetic Equivalent of 2-Lithio or 3-Lithiopropenal. Application to the Synthesis of Juvenile Hormone (JH-II), β-Sinensal, and Jasmonoids.

The ethyl vinyl ether-dibromocarbene adduct was lithiated with butyllithium at -95 deg C in tetrahydrofuran.The resulting lithium carbenoid 3 was allowed to react with various electrophiles to give 1-substituted trans-1-bromo-2-ethoxycyclopropanes (1) in good yields.The trans relationship of Br and OEt groups was found particularly pertinent to the ethanolysis of 1 producing 2-substituted propenal diethyl acetal derivatives.The reaction has been applied to 1-methoxycyclohexene-dibromocarbene adducts, giving rise hereby 2-substituted 2-cyclohepten-1-one dimethyl acetals under ring enlargement.T he transformation has been utilized in the synthesis of a homoterpenoid (JH-II) or a terpenoid (β-sinensal) structure by SN2' substitution of allylic acetates with lithium dimethylcuprate(I) or iron pentacarbonyl respectively.The reaction products of 3 with aldehydes are oxidized with dimethyl sulfoxide to give cyclopropyl ketones whose ethanolysis in the presence of boron trifluoride ether complex gives β-bromo γ-keto aldehyde acetals.Debromination followed by acidic hydrolysis produces γ-keto aldehydes serving as precursors of dihydrojasmone and cis-jasmone.