111957-98-3

Basic information

• Product Name: (S)-4-penten-2-ol
• CAS NO: 111957-98-3
• Molecular Weight: 86.1338
• Mol File: 111957-98-3.mol
• Article Data: 63

Chemical Properties

• CAS DataBase Reference: (S)-4-penten-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-penten-2-ol(111957-98-3)
• EPA Substance Registry System: (S)-4-penten-2-ol(111957-98-3)

Safety Data

• Hazardous Substances Data: 111957-98-3(Hazardous Substances Data)

Upstream product

• 75-07-0 acetaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 930-22-3 epoxybutene 
• 917-54-4 methyllithium 
• 2833-31-0 acetic acid 1-methylbut-3-enyl ester 
• 591-93-5 1,4-Pentadiene 
• 534-15-6 1,1-dimethoxyethane 
• 64549-05-9 allyldibutyltin chloride 
• 598-18-5 2-bromopropanol 
• 3536-96-7 vinylmagnesium chloride 
• 1825-14-5 pentane-1,3-diol 
• 1569-50-2 3-penten-2-ol 
• 2117-11-5 4-pentyn-2-ol 
• 7785-70-8 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 

Downstream Products

• 64584-91-4 phthalic acid mono-(1-methyl-but-3-enyl) ester 
• 64584-92-5 (R)-pent-4-en-2-ol 
• 625-67-2 2,4-dichloropentane 
• 10524-08-0 4-Chlor-pent-1-en 
• 31950-56-8 4-bromopent-1-ene 
• 107-87-9 2-Pentanone 
• 18729-47-0 1-cyclopropyl-2-propanol 
• 107-89-1 acetaldol 
• 117174-90-0 4-(N-(benzyloxycarbonyl)aminomethoxy)-1-pentene 
• 150042-95-8 C₁₅H₂₆OSi₂ 
• 150042-96-9 C₂₅H₃₀OSi₂ 
• 40844-09-5 ((pent-4-en-2-yloxy)methyl)benzene 
• 626-95-9 (2S)-2-methylbutane-1,4-diol 
• 1569-50-2 3-penten-2-ol 

Relevant articles and documents

Sila-Substituted Perfumes and Isosteric Compounds of Perfumes. X. A Novel Route to Sila-β-Ionone

Preparation of sila-β-ionone (14) was possible by a novel route with yields nearly 5 times higher than before, with the formerly unknown 1,1,3-trimethyl-1-silacyclohexanone-2 (6) as a key substance.The nine reaction steps may be seen from Scheme 1. 2-Ethinyl-1,1,3-trimethyl-1-silacyclohexan-2-ol (7) could not be dehydrated to give the analogous silacyclohexene derivative 9.But dehydration was successful in the case of 2-(1-butin-3-ol) substituents; here only the ring but not the chain hydroxyl group was eliminated. - Keywords: Sila-perfumes; Silacyclohexanon-2; Sila-β-ionone

Synthetic Studies toward the C32-C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36-C42 Subunit

The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an α,β-unsaturated δ-lactone followed by α-hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the 1H and 13C NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit. (Chemical Equation Presented).

Barbier-type carbonyl-allylation with allyl compounds and SnCl2 in the presence of PdCl2[PPh2(m-C6H4SO 3Na)]2 under two-phase conditions

The hydrophilic palladium complex efficiently catalyzes the allylation of carbonyl compounds with allyl chlorides or allyl alcohols and SnCl2 under aqueous-organic biphase conditions, which allow us easily to separate the product and to recover the organic solvent from the reaction mixture.

Synthesis and Stereochemical Assignment of Arenolide

The convergent synthesis of candidate stereoisomers of the natural product arenolide was accomplished using recently developed catalytic boron-based reactions. Comparison of the spectral data for candidate structures with that reported for the authentic natural product revealed the likely stereostructure of the natural compound.

Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.