105-29-3

Basic information

• Product Name: 3-Methyl-2-penten-4-yn-1-ol
• Synonyms: 3-Methyl-2-penten-4-yn-1-ol;1-Pentol;3-methylpent-2-en-4-yn-1-ol;1-Hydroxy-3-methyl-2-penten-4-yne;3-methyl-2-penten-4-yn-1-o;3-Methylpenten-2-in-4-ol-1;2-Penten-4-yn-1-ol,3-methyl-
• CAS NO: 105-29-3
• Molecular Formula: C6H8O
• Molecular Weight: 96.12712
• EINECS: 203-284-6
• Mol File: 105-29-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 144.66°C (rough estimate)
• Flash Point: 65.6°C
• Appearance: /
• Density: 0.9253 (estimate)
• Vapor Pressure: 0.46mmHg at 25°C
• Refractive Index: 1.4460 (estimate)
• PKA: 14.22±0.10(Predicted)
• CAS DataBase Reference: 3-Methyl-2-penten-4-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-penten-4-yn-1-ol(105-29-3)
• EPA Substance Registry System: 3-Methyl-2-penten-4-yn-1-ol(105-29-3)

Safety Data

• RIDADR: 2705
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 105-29-3(Hazardous Substances Data)

Usage

General Description

3-Methyl-2-penten-4-yn-1-ol, also known under the CAS number 110-44-1, is a chemical compound which falls under the category of acetylenic alcohols. This colorless, transparent liquid is commonly used in some forms of chemical synthesis. It has a distinct, strong odor and is heavily flammable. Exposure to this substance can potentially cause eye irritation, skin irritation, and respiratory irritation. Therefore, it should be carefully handled with appropriate safety equipment to prevent contact, inhalation, or ingestion.

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

Upstream product

• 121635-27-6 (2E)-3-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-ol 
• 196600-07-4 (E)-1-methoxy-4-(3-methylpent-2-en-4-ynyloxy)benzene 
• 99088-37-6 5-(trimethylsilyl)-3-methyl-3-penten-4-yn-1-ol 
• 71572-66-2 methyl 3-methylpent-2-en-4-ynoate 
• 35504-39-3 3-methyl-1-acetoxy-2-penten-4-yne 
• 3230-69-1 3-methyl-1-penten-4-yn-3-ol 
• 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 
• 121693-79-6 (E)-tert-butyldimethyl-((3-methylpent-2-en-4-yn-1-yl)oxy)silane 
• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 
• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 50516-66-0 5-Trimethylsilyl-3-methyl-pent-1-en-4-in-3-ol 
• 121635-19-6 (Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol 

Downstream Products

• 130584-04-2 (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((Z)-5-hydroxy-3-methyl-pent-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol 
• 14920-89-9 2,3-dimethylfuran 
• 130696-72-9 (1R,4R,6S)-1-<(E)-5-hydroxy-3-methylpent-3-en-1-ynyl>-2,2,6-trimethylcyclohexane-1,4-diol 
• 149694-49-5 methyl (3-methylfuran-2-yl)acetate 
• 130646-73-0 (-)-1(Z)-(1R,4R,6R)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol 
• 130646-72-9 (-)-1(Z)-(1S,4R,6R)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol 
• 130583-96-9 Acetic acid (Z)-5-[(4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-pent-2-en-4-ynyl ester 
• 1435819-21-8 bis[(3E)-5-tert-butyldiphenylsilyloxy-3-methylpent-3-en-1-yne] 
• 1435818-76-0 C₂₅H₂₇BrO₃Si 
• 1435818-59-9 (5Z,2’E)-3-bromo-5-(4’-tert-butyldiphenylsilyloxy-2’-methylbut-2’-enylidene)-5H-furan-2-one 
• 1435818-72-6 ethyl (2E,6E)-2-bromo-8-tert-butyldiphenylsilyloxy-6-methylocta-2,6-dien-4-ynoate 
• 1435819-24-1 ethyl (2Z,6E,3’E)-2-(5’-tertbutyldiphenylsilyloxy-3’-methylpent-3’-en-1’-yn-1’-yl)-8-tert-butyldiphenylsilyloxy-6-methylocta-2,6-dien-4-ynoate 
• 176300-50-8 (2R*,3R*)-2,3-epoxy-3-methyl-4-pentyn-1-ol 
• 63184-82-7 (E)-4,8-dimethyl-3,5-dioxa-7-decen-9-yne 

Relevant articles and documents

Intramolecular pyridone/enyne photocycloaddition: Partitioning of the [4 + 4] and [2 + 2] pathways

Chemical equations presented. Intramolecular photocycloaddition (>290 nm) between a 1,3-enyne and a 2-pyridone is far more selective than the intermolecular version; a three-atom linkage both controls regiochemistry and separates the [2 + 2] and [4 + 4] pathways. All four head-to-head, head-to-tail, tail-to-head, and tail-to-tail tetherings have been investigated. Linkage via the ene of the enyne leads to [2 + 2] products regardless of alkene geometry, whereas linkage through the yne results in [4 + 4] cycloadducts. The bridged 1,2,5-cyclooctatriene products of [4 + 4] cycloaddition are unstable and undergo a subsequent [2 + 2] dimerization reaction.

P(MeNCH2CH2)3N: An efficient catalyst for the desilylation of tert- butyldimethylsilyl ethers

tert-Butyldimethylsilyl (TBDMS) ethers of primary, secondary, and tertiary alcohols and phenolic TBDMS ethers are desilylated to their corresponding alcohols and phenols, respectively, in DMSO, at 80 °C, in 68- 94% yield in the presence of 0.2-0.4 equiv of P(MeNCH2CH2)3N. Using P(i- PrNCH2CH2)3N as the catalyst, 85-97% yields of desilylated alcohols were obtained from TBDMS ethers of 1-octanol, 2-phenoxyethanol, and racemic α- phenyl ethanol. These are the first examples of desilylations of silyl ethers catalyzed by nonionic bases. Both catalysts were much less effective for the desilylation of tert-butyldiphenylsilyl (TBDPS) ethers (22-45% yield) under the same conditions as used for TBDMS ethers. Possible pathways involving nucleophilic attack of the anion of the solvent molecule (generated by the catalyst) at the Si-O bond of silyl ether or a prior activation of the silyl ether by the catalyst via a P-Si interaction followed by nucleophilic attack of the solvent anion are proposed on the basis of 1H and 31P NMR experimental data.

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).

Discovery of a Potent Free Fatty Acid 1 Receptor Agonist with Low Lipophilicity, Low Polar Surface Area, and Robust in Vivo Efficacy

The free fatty acid receptor 1 (FFA1 or GPR40) is established as an interesting potential target for treatment of type 2 diabetes. However, to obtain optimal ligands, it may be necessary to limit both lipophilicity and polar surface area, translating to a need for small compounds. We here describe the identification of 24, a potent FFA1 agonist with low lipophilicity and very high ligand efficiency that exhibit robust glucose lowering effect.