79646-46-1

Basic information

• Product Name: (R)-(-)-(Z)-pent-3-en-2-ol
• Synonyms: (R)-(-)-(Z)-pent-3-en-2-ol
• CAS NO: 79646-46-1
• Molecular Weight: 86.1338
• Mol File: 79646-46-1.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: (R)-(-)-(Z)-pent-3-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-(Z)-pent-3-en-2-ol(79646-46-1)
• EPA Substance Registry System: (R)-(-)-(Z)-pent-3-en-2-ol(79646-46-1)

Safety Data

• Hazardous Substances Data: 79646-46-1(Hazardous Substances Data)

Upstream product

• 42537-25-7 phthalic acid mono-((S)-1-methyl-but-2t-enyl ester) 
• 67-56-1 methanol 
• 1569-50-2 3-penten-2-ol 
• 819852-45-4 C₁₀H₁₃BrOSSe 
• 31001-80-6 3-penten-2-yl acetate 
• 24652-50-4 (Z)-pent-3-en-2-ol 
• 57984-70-0 Pent-3-yn-2-ol 
• 7299-55-0 pent-3-yn-2-one 
• 1126011-07-1 (2S,3Z)-2-(tetrahydropyranyloxy)pent-3-ene 
• 27301-54-8 (S)-(+)-pent-3-yn-2-ol 
• 108-05-4 vinyl acetate 
• 131573-41-6 (2S,3S,4S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-(diphenyl-phosphinoyl)-pentan-3-ol 
• 131573-40-5 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-(diphenyl-phosphinoyl)-pentan-3-one 
• 95482-77-2 (R)-(E)-1-p-tolylsulfinyl-3-penten-2-one 

Downstream Products

• 854260-37-0 ((pent-3-en-2-yloxy)methyl)benzene 
• 940-39-6 D-4-phenoxy-pent-2t-ene 
• 92-52-4 biphenyl 
• 32587-80-7 (S)-4-phenylpentan-2-one 
• 84519-66-4 4-phenyl-(Z)-2-pentene 
• 67110-72-9 (4R)-4-phenylpentan-2-one 
• 735317-55-2 (R)-1-[(4S,5R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-4,5-dihydro-isoxazol-5-yl]-ethanol 
• 863663-25-6 3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R)-1-hydroxyethyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol 
• 200723-19-9 (R,E)-1,2,3-trimethyl-5-(pent-3-en-2-yloxy)benzene 
• 1373874-51-1 (R,E)-3-methyl-1-phenylhex-4-en-3-ol 
• 1373874-52-2 (R,E)-2-cyclohexylpent-3-en-2-ol 
• 1373874-53-3 (S,E)-2-phenylpent-3-en-2-ol 
• 182965-24-8 (Z)-4-hydroxypent-2-en-2-yl diisopropylcarbamate 

Relevant articles and documents

Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study

Gold(I)-catalysed direct allylic etherifications have been successfully carried out with chirality transfer to yield enantioenriched, γ-substituted secondary allylic ethers. Our investigations include a full substrate-scope screen to ascertain substituent effects on the regioselectivity, stereoselectivity and efficiency of chirality transfer, as well as control experiments to elucidate the mechanistic subtleties of the chirality-transfer process. Crucially, addition of molecular sieves was found to be necessary to ensure efficient and general chirality transfer. Computational studies suggest that the efficiency of chirality transfer is linked to the aggregation of the alcohol nucleophile around the reactive π-bound Au-allylic ether complex. With a single alcohol nucleophile, a high degree of chirality transfer is predicted. However, if three alcohols are present, alternative proton transfer chain mechanisms that Erode the efficiency of chirality transfer become competitive.

Erratum: Synthesis of enantioenriched tertiary boronic esters from secondary allylic carbamates. Application to the synthesis of C30 botryococcene (Journal of the American Chemical Society (2012) 134 (7570-7575) DOI: 10.1021/ja303022d)

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Palladium(II)-catalyzed dicarboxymethylation of chiral allylic alcohols: Chirality transfer affording optically active diesters containing three contiguous chiral centers

This manuscript describes the extension of Stille's palladium-catalyzed olefin dicarbonylation reaction to chiral allylic alcohols with chirality transfer to afford the corresponding chiral alcohol functionalized with bis-carbomethoxy esters, containing three contiguous chiral centers, in good to excellent diastereoselectivities (78-98%).