27205-24-9

Usage

Hazard

Moderately toxic by ingestion and skin contact. Low toxicity by inhalation. An eye irritant.

InChI:InChI=1/C6H12OS/c1-3-8-6(2)4-5-7/h5-6H,3-4H2,1-2H3

Upstream product

• 121-44-8 triethylamine 
• 75-08-1 ethanethiol 
• 123-73-9 crotonaldehyde 
• 56-23-5 tetrachloromethane 
• 123-73-9 trans-Crotonaldehyde 

Downstream Products

• 81008-52-8 6-ethylthio-3-hepten-2-one 
• 76938-92-6 6-ethylthio-4-hydroxyheptan-2-one 
• 1258408-38-6 (S,E)-5-ethylthio-1-phenylhex-1-en-3-one 
• 1067606-17-0 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylsulfonyl)propyl]cyclohexane-1,3-dione 
• 1067600-27-4 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylsulfinyl)propyl]-cyclohexane-1,3-dione 
• 1067594-01-7 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylthio)propyl]cyclohexane-1,3-dione 
• 87476-15-1 5-[2-(ethylthio)-propyl]-1,3-cyclohexanedione 
• 68195-07-3 4-(3-ethylsulfanyl-butylidene)-2-phenyl-4H-oxazol-5-one 

Relevant academic research and scientific papers

Cyclohexyl clethodim synthesis process

The invention relates to a cyclohexyl clethodim synthesis process, which comprises: (1) preparing 3-ethylthiobutyraldehyde by using ethanethiol and crotonaldehyde as raw materials; 2) carrying out a reaction on the 3-ethylthiobutyraldehyde and sodium acetoacetate by using secondary amine as a catalyst to prepare 6-ethylthio-3-heptene-2-one; 3) carrying out addition cyclization on the 6-ethylthio-3-heptene-2-one and diethyl malonate, and carrying out hydrolysis decarboxylation to obtain 5-(2-ethylthiopropyl)cyclohexane-1,3-dione; 4) carrying out O-acylation on the 5-(2-ethylthiopropyl)cyclohexane-1,3-dione through propionyl chloride, and carrying out rearrangement to obtain acylated 5-(2-ethylthiopropyl)-2-propionyl-3-hydroxy-2-cyclohexene-1-one; and 5) carrying out a reaction on the 5-(2-ethylthiopropyl)-2-propionyl-3-hydroxy-2-cyclohexene-1-one and 3-chloro-2-propenyl amine hydrochloride to prepare clethodim. According to the invention, the clethodim crude oil with a content of largerthan 97% is obtained by using ethanethiol and crotonaldehyde as the raw materials through the five-step reaction, wherein the total yield is larger than 62%, and the two-step yield of the intermediate 3-chloro-2-propenyl hydroxylamine is larger than 92%; and the method can be used for industrial production and has a good market prospect.

Rhodium-catalysed intermolecular alkyne hydroacylation: The enantioselective synthesis of α- and β-substituted ketones by kinetic resolution

Chemical Equation Presented Cleared up! Intermolecular alkyne hydroacylation represents a new addition to the range of transition- metalcatalysed hydroacylation reactions that can be performed in an enantioselective manner. By using a kinetic resolution procedure, both racemic α- and βsubstituted aldehydes can be converted into the corresponding enantiomerically enriched substituted enone products (see scheme).

NOVEL HERBICIDES

Cyclohexanedione compounds, and derivatives thereof, which are substituted in 5-position, are suitable for use as herbicides.

Rhodium-catalyzed intermolecular chelation controlled alkene and alkyne hydroacylation: Synthetic scope of β-S-substituted aldehyde substrates

The use of β-S-substituted aldehydes in rhodium-catalyzed intermolecular hydroacylation reactions is reported. Aldehydes substituted with either sulfide or thioacetal groups undergo efficient hydroacylation with a variety of electron-poor alkenes, such as enoates, in Stetter-like processes and with both electron-poor and neutral alkynes. In general, the reactions with electron-poor alkenes demonstrate good selectivity for the linear regioisomer, and the reactions with alkynes provide enone products with excellent selectivity for the E-isomers. The scope of the process was shown to be broad, tolerating a variety of substitution patterns and functional groups on both reaction components. A novel CN-directing effect was shown to be responsible for reversing the regioselectivity in a number of alkyne hydroacylation reactions. Catalyst loadings as low as 0.1 mol % were achievable.

Rhodium-catalyzed reductive aldol reactions using aldehydes as the stoichiometric reductants

Chelated acyl rhodium hydrides, generated from the addition of [Rh(dppe)]ClO4 to β-sulfide-substituted aldehydes, can function as the stoichiometric reductants in reductive aldol processes. Unsaturated nitriles, esters, and ketones can be used as enolate equivalents, and a variety of simple α- and β-substituted aldehydes can be employed. The use of a second, more electrophilic, aldehyde allows three-component reactions to be performed. Copyright