80387-31-1

Basic information

• Product Name: 3,5-Nonadien-2-one, (E,E)-
• CAS NO: 80387-31-1
• Molecular Formula: C9H14O
• Molecular Weight: 138.21
• Mol File: 80387-31-1.mol

Chemical Properties

• CAS DataBase Reference: 3,5-Nonadien-2-one, (E,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Nonadien-2-one, (E,E)-(80387-31-1)
• EPA Substance Registry System: 3,5-Nonadien-2-one, (E,E)-(80387-31-1)

Safety Data

• Hazardous Substances Data: 80387-31-1(Hazardous Substances Data)

Upstream product

• 6728-26-3 (E)-2-Hexenal 
• 67-64-1 acetone 
• 27259-09-2 non-3-yn-2-one 
• 118893-64-4 Nona-3,4-dien-2-one 
• 118893-63-3 4-nonyn-2-one 
• 78-95-5 chloroacetone 
• 24764-98-5 2-bromohexanal 
• 58953-13-2 (1E)-1-chlorohex-1-en-3-one 
• 28998-62-1 1,1-dimethoxyhexane-3-one 
• 917-54-4 methyllithium 
• 80387-14-0 2-(benzoyloxy)hexanal 
• 762-39-0 2-chlorohexanal 
• 80387-28-6 (3E)-5-(benzoyloxy)-3-nonen-2-one 

Downstream Products

• 77269-22-8 nonene-4 one-2 
• 75606-70-1 (E)-non-5-en-2-one 
• 14309-57-0 Non-3-en-2-on 

Relevant articles and documents

Highly Stereoselective Isomerization of Ynones to Conjugated Dienones Catalyzed by Transition-Metal Complexes

α,β-Ynones isomerize in the presence of a catalytic amount of IrH5(i-Pr3P)2, RuH2(Ph3P)4-Bu3P, or RuCl2(Ph3P)3-Ph3P in benzene at 35-80 deg C to give (E,E)-α,β:γ,δ-dienones in high yield with high stereoselectivity.This experimentally simple and economica

Stereocontrolled synthesis of 1,3,5-triols by an iteration of asymmetric dihydroxylation and deoxygenation

Asymmetrie dihydroxylation of the Cγ=Cδ bonds in trans-configured α, β, γ, δ-unsaturated esters, carbonate formation, and Pd°-catalyzed deoxygenation of Cγ provided α, β-unsaturated δ-hydroxy esters. Protection and chain-extension provided the corresponding α, β-unsaturated ketones. Their asymmetric dihydroxylation in the presence of phenylboronic acid delivered dioxaborolanes. SmBr2-mediated deoxygenation of Ca, followed by Narasaka-Prasad and Claisen-Tishchenko reductions, respectively, selectively provided monoprotected 1,3syn, 3,5syn-, 1,3syn, 3,5anti-, 1,3anti, 3.5syn-, and 1,3anti, 3,5anticonfigured 1,3,5-triols. Enones with a bulky OSiR3 group at Cδ were dihydroxylated with significantly poorer syn (vs. anti) selectivities. Dominating reagent control modulated by opposing ( mismatched case ) or enhancing ( matched case ) substrate control, respectively, might be responsible.

α-ENONE BY THE REACTION OF ALDEHYDE AND α-BROMOKETONE WITH TRI-n-BUTYLSTIBINE

α-Enones were readily obtained from the reaction of α-bromoketone with aldehydes mediated by tri-n-butylstibine.

New Synthesis of α-Benzoyloxy Aldehydes. Application to the Stereoselective Synthesis of Conjugated (E,E)-Dienoic Esters

A new synthetic method for the preparation of secondary α-benzoyloxy aldehydes (5a-d) and its use in the stereoselective synthesis of conjugated (E,E)-dienone (14) and dienoic esters (9b, 9c, 11, 15b, and 15c) were studied.Two-phase (benzene-H2O) reaction of RCH2CHXCHO (R=CH3, C3H7, C5H11, C7H15; X=Cl, Br) with sodium benzoate (4) in the presence of a catalytic amount of tetrabutylammonium bromide gave the corresponding α-benzoyloxy aldehydes (5a-d) in moderate yields.Compounds 5a-d were converted to γ-benzoyloxy-α,β-unsaturated carbonyl compounds or esters (7b, 7c, 10, 12, 13b, and 13c) either by the TiCl4/py-catalyzed condensation with malonate or acetoacetate or by the Wittig reaction with Ph3P=CHC(O)CH3 and Ph3P=CHCO2Et.Treatment of these compounds with 5 mol percent of (Ph3P)4Pd in refluxing THF afforded the corresponding conjugated (E,E)-dienones and dienoic esters stereoselectively.The reaction sequence was further extended to the stereoselective synthesis of ethyl (2E,4E,6E)-2,4,6-dodecatrienoate (18) and pellitorine (21).