4168-01-8

Usage

Appearance

Clear, colorless liquid

Odor

Strong, fruity

Occurrence

Commonly found in essential oils, particularly in geranium and lemon oils

Usage

Used in the fragrance industry as a flavoring agent and as a component in perfumes and cosmetics, and as a chemical intermediate in the synthesis of various other compounds

Biological activities

Potential antioxidant, anti-inflammatory, and anti-cancer agent

Safety

Corrosive substance that can cause irritation to the skin, eyes, and respiratory tract, and should be handled with care.

Upstream product

• 4786-26-9 2,2,3-trimethyl-3-butenenitrile 
• 1727-59-9 methyl 2,2,3-trimethylbut-3-enoate 
• 220264-25-5 ethyl 3-chloro-2,2,3-trimethylbutyrate 
• 124-38-9 carbon dioxide 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 62817-86-1 3-hydroxy-2,2,3-trimethyl-butyric acid ethyl ester 
• 563-78-0 2,3-Dimethyl-1-butene 
• 563-79-1 2,3-Dimethyl-2-butene 
• 160115-34-4 benzyl 2,2-dimethyl-3-oxobutanoate 
• 4786-19-0 3-methyl-3-butene nitrile 
• 4786-24-7 3,3-dimethylacrylonitrile 
• 4786-37-2 2,3-dimethyl-2-butenenitrile 
• 597-04-6 ethyl 2,2-dimethyl-3-oxobutanoate 
• 86425-96-9 3-Hydroxy-2,2,3-trimethyl-butyric acid methyl ester 

Downstream Products

• 563-80-4 3-methyl-butan-2-one 
• 92223-72-8 hydroxy-trimethyl-succinic acid 
• 1315320-12-7 C₂₁H₃₁N₃O₆ 
• 1315320-11-6 C₁₃H₁₇NO₂ 
• 6968-27-0 2,2,3-trimethyl-butyric acid amide 
• 211696-56-9 2,2,3-Trimethyl-but-3-enoic acid (2-chloro-benzyl)-hydroxy-amide 
• 563-79-1 2,3-Dimethyl-2-butene 
• 49714-52-5 2,2,3-trimethylbutanoic acid 

Relevant academic research and scientific papers

Die Acylierung von Acetylenen mit β,γ-ungesaettigten Saeurechloriden. Eine neue Synthese von 5-substituierten 2-Cyclopentenonen

The acylation of acetylenes with α,α-disubstituted, β,γ-unsaturated acid chlorides under Friedel-Crafts-type conditions leads to 5-substituted 2-cyclopentenones.Phenols are formed with β,γ-unsaturated acid chlorides bearing at least one α-H-atom.These transformations are explained by the intramolecular cyclization of the initially formed vinyl cation, which, in the cases of α,α-disubstituted acid chlorides, is formed by ring contraction.The reaction leading to 2-cyclopentenones is applied to the syntesis of some spirodeca-2,6-dienones.

THE ACYLATION OF ACETYLENES WITH β,γ-UNSATURATED ACID CHLORIDES: A NEW SYNTHESIS OF 5,5-DISUBSTITUTED 2-CYCLOPENTENONES

The acylation of acetylenes with α,α-disubstituted, β,γ-unsaturated acid chlorides was found to lead to 5,5-disubstituted 2-cyclopentenones by a novel intramolecular cyclization-rearrangement process.

A Light/Ketone/Copper System for Carboxylation of Allylic C-H Bonds of Alkenes with CO2

A photo-induced carboxylation reaction of allylic C-H bonds of simple alkenes with CO2 is prompted by means of a ketone and a copper complex. The unique carboxylation reaction proceeds through a sequence of an endergonic photoreaction of ketones with alkenes forming homoallyl alcohol intermediates and a thermal copper-catalyzed allyl transfer reaction from the homoallyl alcohols to CO2 through C-C bond cleavage. An allylic C-H bond of simple alkenes is carboxylated with CO2 in the presence of a substoichiometric amount of a ketone and a catalytic amount of a copper complex under UV irradiation (see scheme).

COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS

The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

Metal-free oxyaminations of alkenes using hydroxamic acids

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.

Catalytic hydromagnesation of di- and polymethyl-substituted 1,3-butadienes

Hydromagnesation of di- and polymethyl-substituted 1,3-butadienes with alkylmagnesium halides in the presence of Ni(PPh3)2Cl2 and NiPy4Cl2 was studied.

Restricted stereochemistry of solvation of allylic lithium compounds: Structural and dynamic consequences

Several 1-sila allylic lithium compounds have been prepared with potential ligands for Li substituted at the 2-position. They are [2-[[cis-2,5-bis(methoxymethyl)-1-pyrrolidinyl]methyl]-1-(trimethylsilyl)allyl] lithium (22), [2-[[cis-2,5-bis(methoxymethyl)-1-pyrrolidinyl]methyl]-1-(dimethylethylsilyl) allyl]lithium(23), [2-[[bis-(2-methoxyethyl)amino]methyl]-1-(dimethylethylsilyl)allyl]lithium (24), [2-[[bis(2-methoxyethyl)amino]methyl]-1-(tert-butyldimethylsilyl)allyl]lithium (25), and [2-[2-[bis(2-methoxyethyl)amino]-1,1-dimethylethyl](ethyl-dimethylsilyl)] allyllithium (26). Using diethyl ether or THF solutions all these compounds exhibited one bond 13C, 7Li spin coupling of ～8 Hz, a 1:1:1:1 13C NMR pattern indicating monomeric structures; all show ligand resonances to be magnetically nonequivalent and reveal C1, C3 13C NMR shifts of about 40 and 75 δ which lie between those for model delocalized 1 and localized species 2. These compounds are concluded to be examples of the heretofore missing folded, internally tridentately coordinated partially delocalized structures with small detectable C, Li covalence. The exception is 25 which, in diethyl ether, consists of a rapidly interconverting equilibrium mixture of localized and delocalized more solvated forms, the former prevailing at 300 K and progressively converting mainly to the latter by 180 K. NMR line shape analysis of the diastereotopic gem methylsilyl 13C resonances as well as that due to the ligand carbons shows that all these line shape changes are due to the dynamics of inversion at lithium-bound carbon and that other ligand reorientation processes are slower than carbanide inversion; for inversion, ΔH? is found to be 6-9 kcal?mol-1, respectively. Averaging with increasing temperature of the 13C, 7Li spin coupling in 24 provides the dynamics of bimolecular carbon lithium bond exchange with ΔH? of 12 kcal?mol-1. Mechanisms are proposed on the basis of the data. We ascribe restricted stereochemistry of ligand lithium coordination to be responsible for these unusual internally coordinated structures.

New synthesis of 2-alkyl-4,4-dimethyl-5-halomethylisoxazolidin-3-ones via intramolecular halocyclization of N-alkyl-2,2-dimethyl-3-butenohydroxamic acids

N-Alkyl-2,2-dimethyl-3-butenohydroxamic acids and their cyclic derivatives were halocyclized by iodine monochloride, N-bromosuccinimide, or N-chlorosuccinimide to afford the corresponding 2-alkyl-4,4-dimethyl-5-halomethylisoxazolidinones and 5-membered ring fused isoxazolidinones in excellent yields.

A Facile Method for Synthesis of Three Carbon-Homologated Carboxylic Acid by Regioselective Ring-opening of β-Propiolactones with Organocopper Reagents

Organocopper reagents, such as diorganocuprates, organocopper-tributylphosphine, and Grignard reagents in the presence of a copper (I) salt, reacted with β-propiolactones by regioselective β-carbon-oxygen fission to give 3-substituted propionic acids.Among these three kinds of organocopper reagents, diorganocuprate, especially halomagnesium cuprate gave the highest yields of the acids, which was remarkably observed in the ring-opening of sterically hindered β-propiolactones such as β-methyl- and α,β-dimethyl-β-propiolactones and also in the reactions using the organocopper reagents with vinyl and allyl substituents.The ring-opening of β-propiolactone was confirmed to proceed by SN2 pathway with predominant inversion of configuration of the β-carbon by using the reaction of cis-α,β-dimethyl-β-propiolactone with di-tert-butylcuprate to afford syn-2,3,4,4-tetramethylpentanoic acid.