39495-82-4

Usage

Uses

Used in Chemical Synthesis:
ETHYL 5-METHYL-5-HEXENOATE is used as a key intermediate in the preparation of Isoxazoline compounds, which are important in the development of pharmaceuticals and other chemical products. Its unique structure allows for the formation of these compounds through various chemical reactions.
Used in Activation of C-F Bonds:
ETHYL 5-METHYL-5-HEXENOATE is used as a reagent in the activation of primary and secondary Benzylic and tertiary alkyl (sp3)C-F bonds. This activation process takes place within a self-assembled molecular container, which provides a controlled environment for these reactions to occur. This application is significant in the field of organic chemistry, as it enables the selective activation of specific bonds, leading to the synthesis of more complex and functionalized molecules.

InChI:InChI=1/C9H16O2/c1-4-11-9(10)7-5-6-8(2)3/h2,4-7H2,1,3H3

Upstream product

• 3128-06-1 5-ketohexanoic acid 
• 13984-57-1 ethyl 5-oxohexanoate 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 80352-66-5 4-mesyloxy-2-methylbutene 
• 105-53-3 diethyl malonate 
• 115-11-7 isobutene 
• 140-88-5 ethyl acrylate 
• 1120-72-5 2-Methylcyclopentanone 
• 64-17-5 ethanol 
• 67-68-5 dimethyl sulfoxide 
• 176376-86-6 diethyl 2-(3-methyl-3-buten-1-yl)malonate 
• 763-32-6 2-methyl-1-buten-4-ol 
• 7425-53-8 ethyl 4-iodobutyrate 

Downstream Products

• 55170-74-6 5-methylhex-5-enoic acid 
• 13984-57-1 ethyl 5-oxohexanoate 

Relevant academic research and scientific papers

Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst

The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Preparation method of 5-methyl-5-ethyl hexenoate

The invention discloses a preparation method of 5-methyl-5-ethyl hexenoate. The method comprises the following steps: 1) adding ethyl acrylate, benzene and a catalyst into a four-neck flask, controlling the temperature to be 25-30 DEG C, introducing isobutene, preserving heat for 24-60 hours, adding a sodium bicarbonate aqueous solution, stirring for 0.5-1 hour, adding a mixed solution of hydrochloric acid and water, stirring for 0.5 hour, standing for 0.5 hour, layering, and washing with water to obtain a water layer and a benzene layer; and 2) adding the benzene layer into a barrel, adding adehydrating agent, dehydrating, concentrating, carrying out normal pressure distillation and reduced pressure distillation in sequence, and collecting the azeotropic fraction to obtain the 5-methyl-5-ethyl hexenoate. According to the preparation method of the 5-methyl-5-ethyl hexenoate, aluminum trichloride and tungsten hexachloride are synergistically used as catalysts, the total yield can reach46.7% or above, anhydrous sodium sulfate and n-butyl alcohol are used as dehydrating agents, and the product purity can reach 97.5% or above; and the preparation method disclosed by the invention issimple to operate and relatively low in cost.

Radical Cyclization of Epoxy Vinyl- and Allylsulfones Promoted by Titanocene Chloride

A titanocene-mediated intramolecular radical addition of different epoxy vinyl- and allylsulfones has been achieved. Five- and six-membered ring products were obtained in good to excellent yields in the presence of both 2.2 and 0.2 equiv of Cp2TiCl. A novel double-activation strategy allowed us to achieve small-size rings such as cyclobutanes and cyclopropanes. (Chemical Equation Presented).

METHOD FOR PRODUCING ALKYL 5-METHYL-5-HEXENOATE

A decarboxylation reaction of a (3-methyl-3-butenyl)malonic acid dialkyl ester, carried out by heating in the presence of water and a base, produces an alkyl 5-methyl-5-hexenoate. The decarboxylation reaction produces the alkyl 5-methyl-5-hexenoate inexpensively and effectively. The base can optionally be a tertiary amine compound or a heterocyclic amine compound. Producing the alkyl 5-methyl-5-hexenoate can optionally further include removing an alcohol.

Nuclear Synthons: Mesyltriflone as an Olefin Polyanion Equivalent

Mesyltriflone (CF3SO2CH2SO2CH3) is developed as a nuclear synthon reagent capable first of multiple constructions such as alkylations then of Ramberg-Baecklund elimination to a substituted olefin.The alkylations are clean and regiospecific, often amenable to one-pot operation, and in most cases the elimination is smooth.A variety of examples is presented to establish the scope of the method, and the mechanism and stereochemistry are discussed.