64584-92-5

Basic information

• Product Name: (R)-(-)-PENTEN-2-OL
• Synonyms: (R)-(-)-2-HYDROXYPENT-4-ENE;(R)-(-)-PENTEN-2-OL;(r)-(-)-4-penten-2-ol;(1R)-1-Methyl-3-butene-1-ol;(2R)-4-Pentene-2-ol;(2R)-pent-4-en-2-ol
• CAS NO: 64584-92-5
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• Product Categories: API intermediates;Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 64584-92-5.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 115-116 °C(lit.)
• Flash Point: 78 °F
• Appearance: /
• Density: 0.837 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4240(lit.)
• PKA: 15.10±0.20(Predicted)
• Water Solubility: Soluble in water, 4.526 mg/L @ 25°C.
• CAS DataBase Reference: (R)-(-)-PENTEN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-PENTEN-2-OL(64584-92-5)
• EPA Substance Registry System: (R)-(-)-PENTEN-2-OL(64584-92-5)

Safety Data

• Hazard Codes: H226
• Statements: 10
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 64584-92-5(Hazardous Substances Data)

Usage

Uses

(R)?-?(-?)?-?4-?Penten-?2-?ol is a reactant in the synthesis of aigialomycin D and its analogs that inhibits protein kinases related to cancer pathways.

Upstream product

• 688-61-9 Triallylborane 
• 75-07-0 acetaldehyde 
• 143143-11-7 2,2,2-Trifluoro-N-[(1R,2R)-1-methyl-2-((R)-1-methyl-but-3-enyloxy)-2-phenyl-ethyl]-acetamide 
• 1826-67-1 vinyl magnesium bromide 
• 15448-47-2 (R)-propylene oxide 
• 108-05-4 vinyl acetate 
• 111957-98-3 Pent-4-en-2-ol 
• 90-82-4 pseudoephedrine 
• 64584-91-4 phthalic acid mono-(1-methyl-but-3-enyl) ester 
• 760181-72-4 (R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol 
• 847049-72-3 1-methoxy-4-{[(2S)-pent-4-en-2-yloxy]methyl}benzene 
• 142561-89-5 (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 874660-40-9 (R)-2-(4-Methoxy-benzyloxy)-pent-4-enal 
• 1384108-64-8 C₅H₉O₄S^(1-)*Na⁽¹⁺⁾ 

Downstream Products

• 300-85-6 3-Hydroxybutyric acid 
• 139079-91-7 (4R)-1-penten-4-yl-(αR)-α-methoxy-α-trifluoromethylphenylacetate 
• 335161-36-9 3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid 1-methyl-but-3-enyl ester 
• 871565-63-8 benzyl 3,5-dimethyl-4-[(S)-(1-methyl-but-3-enyloxycarbonyl)methyl]-1H-pyrrole-2-carboxylate 
• 853645-34-8 2,4-dihydroxy-6-methylbenzoic acid 1-methylbut-3-enyl ester 
• 864155-65-7 [(1R,2S,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-cyclohex-3-enyl]-acetic acid (S)-1-methyl-but-3-enyl ester 
• 936913-81-4 4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester 
• 946063-60-1 (S)-pent-4-en-2-yl 2,4-bis(methoxymethoxy)-6-methylbenzoate 
• 906374-58-1 2,4-bis-ethoxymethoxy-6-methyl-benzoic acid 1-methyl-but-3-enyl ester 
• 1007314-11-5 2,4-bis-ethoxymethoxy-6-{2-[(methoxy-methyl-carbamoyl)-methyl]-hex-5-enyl}-benzoic acid 1-methyl-but-3-enyl ester 
• 869336-70-9 (+)-(2R,4R,4'R)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 
• 869336-63-0 (-)-(2R,4S,4'R)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 
• 879282-80-1 (R)-5-{(1S,3R,5R,6S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-triisopropylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]hept-1-yl}-pentan-2-ol 
• 869336-56-1 (+)-(2R,4R,4'R)-6-(4'-acetoxypentyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 

Relevant articles and documents

Asymmetric synthesis of (+)-stagonolide C and (-)-aspinolide A via organocatalysis

A new enantioselective synthesis of two important fungal metabolites, (+)-stagonolide C and (-)-aspinolide A, has been described from readily available raw materials. Proline catalyzed asymmetric α-aminooxylation and Jorgensen's epoxidation of aldehydes a

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.

A facile, efficient and selective deprotection of p-methoxy benzyl ethers using zinc (Ii) trifluoromethanesulfonate

Deprotection is significant and conducted over mild reaction conditions, in order to restrict any more side reactions with sensitive functional groups as well as racemization or epimerization of stereo center because the protective groups are often cleaved at last stage in the synthesis. P-Methoxy benzyl (PMB) ether appears unique due to its easy introduction and removal than the other benzyl ether protecting groups. A facile, efficient and highly selective cleavage of P-methoxy benzyl ethers was reported by using 20 mole% Zinc (II) Trifluoromethanesulfonate at room temperature in acetonitrile solvent over 15-120 min. time period. To study the generality of this methodology, several PMB ethers were prepared from a variety of substrates having different protecting groups and subjected to deprotection of PMB ethers using Zn(OTf)2 in acetonitrile. In this methodology, zinc triflate cleaves only PMB ethers without affecting acid sensitivity, base sensitivity and also chiral epoxide groups.