5673-98-3

Basic information

• Product Name: 2-Methyl-4-penten-1-ol
• Synonyms: 2-Methyl-4-penten-1-ol;4-Penten-1-ol, 2-methyl-
• CAS NO: 5673-98-3
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• Mol File: 5673-98-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 22.55°C (estimate)
• Boiling Point: 152.63°C (estimate)
• Appearance: /
• Density: 0.8489 (estimate)
• Refractive Index: 1.4289 (estimate)
• PKA: 14.99±0.10(Predicted)
• CAS DataBase Reference: 2-Methyl-4-penten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-4-penten-1-ol(5673-98-3)
• EPA Substance Registry System: 2-Methyl-4-penten-1-ol(5673-98-3)

Safety Data

• Hazardous Substances Data: 5673-98-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 7, p. 875, 1966 DOI: 10.1016/0005-2760(66)90119-6

Upstream product

• 80697-95-6 (4R,5S)-4-methyl-3-((S)-2-methylpent-4-enoyl)-5-phenyloxazolidin-2-one 
• 96864-02-7 (R)-2-Methyl-pent-4-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 175272-36-3 (4R)-4-Benzyl-3-[(2S)-2-methyl-4-pentenoyl]-1,3-oxazolidin-2-one 
• 303123-83-3 (1''S,2S,2'R)-1-[2'-(1''-tert-butyldiphenylsiloxyethyl)-4'H-benzo[d][1',3']oxazin-1'-yl]-2-methylpent-4-en-1-one 
• 130004-39-6 allyltitanium triphenoxide 
• 75-56-9 methyloxirane 
• 7393-43-3 tetraallyl tin 
• 15448-47-2 (R)-propylene oxide 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 132857-79-5 (S)-2-methylpent-4-en-1-yl 4-methylbenzenesulfonate 
• 5187-71-3 2-methyl-4-pentenal 
• 88001-61-0 5-((tert-butyldiphenylsilyl)oxy)-4-methylpentan-1-ol 
• 132857-79-5 toluene-4-sulfonic acid 2-methylpent-4-enyl ester 
• 391208-05-2 (S)-1-((2-methylpent-4-enyloxy)methyl)benzene 
• 144693-95-8 tert-butyldipheny((2-methylpent-4-en-1-yl)oxy)silane 
• 190005-22-2 [2R]-Benzyl 2-methyl-4-penten-1-yl ether 
• 944994-56-3 C₁₃H₂₀O₂ 
• 944994-57-4 C₂₀H₂₆O₄S 
• 944994-47-2 C₁₃H₁₉IO 
• 944994-48-3 C₃₄H₅₄O₄ 
• 944994-50-7 C₃₄H₄₈Br₂O₆ 
• 944994-42-7 C₃₄H₄₆Br₂O₆ 
• 277297-33-3 2-((S)-1-Allyl-pentyl)-5-((S)-2-methyl-pent-4-enyl)-benzene-1,3-diol 

Relevant articles and documents

Enantiopure 2,9-Dideuterodecane – Preparation and Proof of Enantiopurity

(R,R)- and (S,S)-(2,9-2H2)-n-Decane were prepared regio- and stereospecifically in 25–26 % yield over five steps from commercially available enantiopure (R)- and (S)-propylene oxide, respectively. The synthetic procedure involved nucleophilic displacement of (R)- and (S)-4-toluenesulfonic acid 1-methyl-4-pentenyl ester with LiAlD4 to furnish the respective (5-2H)-1-hexenes. Subsequent olefin metathesis and reduction of the double bond furnished the title compounds. The optical purity of (R,R)- and (S,S)-(2,9-2H2)-n-decane could not be determined by chromatography or polarimetry. Therefore, (R,R)- and (R,S)-(5-2H)-3-hydroxy-2-hexanone were prepared from their respective hexenes by Wacker oxidation, followed by enantioselective α-hydroxylation. The enantiopurity could then be determined by NMR spectroscopy because the stereospecifically deuterated hydroxyketones showed separated signals for the subterminal carbon atom (C-5) in the 13C NMR spectrum.

Syntheses of (-)-epothilone B

Two efficient routes for the total synthesis of (-)-epothilone B are reported. One strategy is based on ring-closing metathesis, and a second synthesis on a macrolactonization. The key fragments are available on large scale to provide sufficient material for biological tests. Thiazole fragment 4 was obtained by an improved route starting from (S)-malic acid. The first synthesis is based on our preceding paper. The critical trisubstituted double bond C12-13 in our second approach was constructed by a highly efficient Pd- mediated coupling reaction. Ring closure was achieved by macrolactonization.

Allyltitanium Triphenoxide: Selective Cleavage of Oxiranes at the More Substituted Carbon Atom

Allyltitanium triphenoxide was found to be an excellent reagent for regioselective allylation at the more substituted carbon atom of oxiranes.