6153-06-6

Basic information

• Product Name: (E)-3-Methylpent-2-en-4-yn-1-ol
• Synonyms: (E)-3-Methylpent-2-en-4-yn-1-ol;trans-3-Methyl-2-penten-4-ynol;Enynic Alcohol;Trans-3-Methyl-2-Penten-4-Yn-1-Ol;trans-3-Methyl-2-penten-4-yn-1-ol, GC 90%;trans-3-Methyl-2-pentene-4-yn-1-ol;(E)-3-Methyl-2-penten-4-yn-1-ol
• CAS NO: 6153-06-6
• Molecular Formula: C₆H₈O
• Molecular Weight: 96.13
• EINECS: 228-169-8
• Mol File: 6153-06-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 171°C
• Flash Point: 65°C
• Appearance: clear to yellowish liquid
• Density: 0.940
• Refractive Index: 1.4445-1.4465
• PKA: 13.80±0.10(Predicted)
• CAS DataBase Reference: (E)-3-Methylpent-2-en-4-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-Methylpent-2-en-4-yn-1-ol(6153-06-6)
• EPA Substance Registry System: (E)-3-Methylpent-2-en-4-yn-1-ol(6153-06-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 1760
• Hazardous Substances Data: 6153-06-6(Hazardous Substances Data)

Usage

Uses

(E)-3-Methylpent-2-en-4-yn-1-ol is a terminal alkyne and a useful building block for organic synthesis.

InChI:InChI=1/C6H8O/c1-3-6(2)4-5-7/h1,4,7H,5H2,2H3/b6-4+

Upstream product

• 121693-79-6 (E)-tert-butyldimethyl-((3-methylpent-2-en-4-yn-1-yl)oxy)silane 
• 71572-66-2 methyl 3-methylpent-2-en-4-ynoate 
• 35504-39-3 3-methyl-1-acetoxy-2-penten-4-yne 
• 99088-37-6 5-(trimethylsilyl)-3-methyl-3-penten-4-yn-1-ol 
• 3230-69-1 3-methyl-1-penten-4-yn-3-ol 
• 196600-07-4 (E)-1-methoxy-4-(3-methylpent-2-en-4-ynyloxy)benzene 
• 53635-18-0 3-methyl-2-penten-4-yn-1-al 
• 470671-44-4 (E)-5-bromo-3-methyl-pent-2-en-4yn-1-ol 
• 121635-27-6 (2E)-3-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-ol 
• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 

Downstream Products

• 29443-88-7 (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trien-4-yn-1-ol 
• 76681-72-6 2E,4E-6-acetoxy-4-methyl-2,4-hexadienyltriphenylphosphonium bromide 
• 58508-37-5 9E,9Z-9,13-dimethyl-7-(1,5-dimethyl-1-ethoxycarbonyl-4-oxo-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-ol 
• 76681-57-7 9E,9Z-9,13-dimethyl-7-(1,5-dimethyl-1-ethoxycarbonyl-4-oxo-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-yl acetate 
• 516518-77-7 (E)(E) 5-[3-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-phenyl]-3-methyl-pent-2-en-4-yn-1-ol 
• 196600-07-4 (E)-1-methoxy-4-(3-methylpent-2-en-4-ynyloxy)benzene 
• 136786-41-9 tert-Butyl-[(6E,8E,10E)-(2S,4S,5S)-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-2,4,10-trimethyl-dodeca-6,8,10-trienyloxy]-diphenyl-silane 
• 910042-96-5 6-{(1E,3S,5S,6S,7E,9E,11E)-[13-(4-methoxybenzyloxy)-6-(methoxymethoxy)-1,3,5,11-tetramethyltrideca-1,7,9,11-tetraen-1-yl]}-2,2-dimethyl-4H-1,3-dioxen-4-one 
• 910043-30-0 (2S,4S,5S,6E,8E,10E)-12-(4-methoxybenzyloxy)-5-(methoxymethoxy)-2,4,10-trimethyldodeca-6,8,10-trienal 
• 910043-13-9 (2S,4S,5S,6E,8E,10E)-12-(4-methoxybenzyloxy)-5-(methoxymethoxy)-2,4,10-trimethyldodeca-6,8,10-trien-1-ol 
• 910043-09-3 diphenyl[(2E,4E)-6-[(4-methoxyphenyl)methoxy]-4-methylhexa-2,4-dien-1-yl]phosphine oxide 
• 910043-10-6 (E)-6-[(4-methoxyphenyl)methoxy]-4-methylhex-4-en-2-yn-1-ol 
• 910043-11-7 (2E,4E)-6-[(4-methoxyphenyl)methoxy]-4-methylhexa-2,4-dien-1-ol 
• 910043-12-8 (2E,4E)-1-chloro-6-[(4-methoxyphenyl)methoxy]-4-methylhexa-2,4-diene 

Relevant articles and documents

Chiral 1,2,3-Triazolium Salt Catalyzed Asymmetric Mono- and Dialkylation of 2,5-Diketopiperazines with the Construction of Tetrasubstituted Carbon Centers

Novel asymmetric mono- and dialkylation reactions of α-substituted 2,5-diketopiperazines catalyzed by new chiral spirocyclic-amide-derived triazolium organocatalysts have been developed, resulting in a range of enantioenriched 2,5-diketopiperazine derivatives containing one or two tetrasubstituted carbon stereocenters. The reactions feature high yields (up to 98%), and excellent cis-diastereo- and enantioselectivities (up to >20:1 dr, >99 % ee), and they provide a new asymmetric synthetic approach to important functionalized 2,5-diketopiperazine skeletons. Furthermore, a possible reaction mechanism was proposed based on both control experiments and extensive DFT calculations.

Synthetic study of an intermediate towards paracentrone

Paracentrone (1), the second naturally occurring C31-methyl ketone apocarotenoid from fucoxanthin (2), was first isolated from the sea urchin Paracentrotus lividus. In this study, we focused on this carotenoid metabolite and report on a synthetic approach towards (3E)-(5R)-[(2R,4S)-2-hydroxy-4-(tert-butyldimethylsilyl)oxy-2,6,6-trimethylcyclohexylidene]-1-iodo-4-methyl-1,3, 5-hexatriene (5), a synthetic intermediate towards 1. This was obtained from epoxy acetylene (11) via (2E)-(4R)-[(2R,4S)-2-hydroxy-4-(tert-butyldimethyl-silyl)oxy-2,6,6-trimethylcyclohexylidene]-3-methylpenta-2,4-dien-1-ol (7).

Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes

This paper describes the development of an integrated approach for the preparation of diverse furan derivatives from acetylenic alcohols by gold and palladium catalyzed π-activation chemistry. Notably, this new method was found to be amenable to cycloocty