1001-75-8

Basic information

• Product Name: 4-Pentenoic acid, 4-methyl-
• Synonyms: 4-Pentenoic acid, 4-methyl-;4-Methyl-4-pentenoic acid
• CAS NO: 1001-75-8
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114
• Mol File: 1001-75-8.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 199℃
• Flash Point: 96℃
• Appearance: /
• Density: 0.974
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Pentenoic acid, 4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentenoic acid, 4-methyl-(1001-75-8)
• EPA Substance Registry System: 4-Pentenoic acid, 4-methyl-(1001-75-8)

Safety Data

• Hazardous Substances Data: 1001-75-8(Hazardous Substances Data)

Usage

General Description

4-Pentenoic acid, 4-methyl- is a chemical compound that belongs to the class of organic compounds known as short-chain fatty acids. It is a four-carbon unsaturated carboxylic acid with a methyl substituent at the 4-position. 4-Pentenoic acid, 4-methyl- is considered to be basically insoluble (in water) and can be found in low concentrations in essential oils. It is primarily used in the flavor and fragrance industry as an additive to provide a fruity aroma, and it is also used in the production of polymers and pharmaceuticals. Additionally, this compound can also be found in various foods and beverages as a natural flavoring agent.

Upstream product

• 129250-82-4 (2-methyl-5-oxo-tetrahydro-[2]furyl)-acetic acid 
• 1067-09-0 1,3-dichloro-2-(chloromethyl)-2-methylpropane 
• 124-38-9 carbon dioxide 
• 4911-54-0 ethyl 4-methyl-4-pentenoate 
• 463-49-0 1,2-propanediene 
• 22508-64-1 4-methyl-4-penten-1-ol 
• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 123-76-2 levulinic acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 34998-36-2 3-methylenebutanecarbonitrile 
• 763-32-6 2-methyl-1-buten-4-ol 
• 781-03-3 isopentenyl tosylate 
• 50598-40-8 dimethyl (2-methyl-2-propenyl)-propanedioate 

Downstream Products

• 123808-97-9 (3R,7aS)-3-isopropyl-7a-methyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one 
• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 
• 1082606-19-6 C₁₆H₂₁NO₃S 
• 1310539-05-9 5-methyl-1-(4-nitrophenylsulfonyl)-5-(3-(triisopropylsilyl)prop-2-ynyl)pyrrolidin-2-one 
• 1310538-75-0 4-methyl-N-(4-nitrophenylsulfonyl)pent-4-enamide 

Relevant articles and documents

Stereoselection in Intramolecular Diels-Alder Reactions of 2-Cyano-1-azadienes: Indolizidine and Quinolizidine Synthesis

Progress toward understanding the scope and diastereoselectivity of intramolecular Diels-Alder reactions using 2-cyano-1-azadienes is described herein. The resulting cyanoenamine products are underutilized intermediates in organic synthesis. Assembly of the Diels-Alder precursors was achieved using an improved imine condensation/oxidative cyanation protocol. By this method, several highly substituted indolizidine and quinolizidine architectures were constructed. Quantum mechanical DFT calculations at the B3LYP/6-31+G(d) level of theory were performed for these cyclizations and provide insights into the origins of the observed diastereoselectivities.

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Total synthesis and evaluation of a key series of C5-substituted vinblastine derivatives

A remarkably concise seven- to eight-step total synthesis of a systematic series of key vinblastine derivatives is detailed and used to characterize the importance and probe the role of the C5 ethyl substituent (R = H, Me, Pr, CH=CH2, C≡CH, CH2OH, and CHO vs Et). The analogues, which bear deep-seated structural changes accessible only by total synthesis, were prepared using a powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles ideally suited for use in the assemblage of the vindoline-derived lower subunit followed by their incorporation into the vinblastine analogues through the use of a single-step biomimetic coupling with catharanthine. The evaluation of the series revealed that the tubulin binding site surrounding this C5 substituent is exquisitely sensitive to the presence (Et > H, 10-fold), size (Me ≤Et > Pr, 10-fold), shape (Et > CH=CH2 and C≡CH, >4-fold), and polarity (Et > CHO > CH2OH, >10-20-fold) of this substituent and that on selected occasions only a C5 methyl group may provide analogues that approach the activity observed with the naturally occurring C5 ethyl group.

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Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes

A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.

Iridium-Catalyzed Aerobic α,β-Dehydrogenation of γ,δ-Unsaturated Amides and Acids: Activation of Both α- And β-C-H bonds through an Allyl-Iridium Intermediate

Direct aerobic α,β-dehydrogenation of γ, δ-unsaturated amides and acids using a simple iridium/copper relay catalysis system is described. We developed a new strategy that overcomes the challenging issue associated with the low α-acidity of amides and acids. Instead of α-C-H metalation, this reaction proceeds by β-C-H activation, which results in enhanced α-acidity. Conjugated dienamides and dienoic acids were synthesized in excellent yield with this reaction, which uses a simple reaction protocol. Mechanistic experiments suggest a catalyst resting state mechanism in which both α-C-H and β-C-H cleavage is accelerated.