157952-85-7

Basic information

• Product Name: 2-IODO-4,4-DIMETHYL-CYCLOHEX-2-ENONE
• Synonyms: 2-IODO-4,4-DIMETHYL-CYCLOHEX-2-ENONE;2-iodo-4,4-dimethyl-2-cyclohexen-1-one
• CAS NO: 157952-85-7
• Molecular Formula: C₈H₁₁IO
• Molecular Weight: 250.07681
• Mol File: 157952-85-7.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-IODO-4,4-DIMETHYL-CYCLOHEX-2-ENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODO-4,4-DIMETHYL-CYCLOHEX-2-ENONE(157952-85-7)
• EPA Substance Registry System: 2-IODO-4,4-DIMETHYL-CYCLOHEX-2-ENONE(157952-85-7)

Safety Data

• Hazardous Substances Data: 157952-85-7(Hazardous Substances Data)

Upstream product

• 1073-13-8 4,4-dimethylcyclohexenone 
• 4648-54-8 trimethylsilylazide 
• 4255-62-3 4,4-dimethylcyclohexane-1-one 

Downstream Products

• 181276-75-5 4,4-dimethyl-2-((trimethylsilyl)ethynyl)cyclohex-2-enone 
• 341497-26-5 (R)-4,4-dimethyl-2-iodo-2-cyclohexen-1-ol 
• 118653-39-7 methyl 3,3-dimethyl-6-oxocyclohex-1-ene-1-carboxylate 
• 887945-81-5 5-(3,3-dimethyl-6-oxo-cyclohex-1-enyl)-4-vinyl-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 1123311-92-1 4,4-dimethyl-2-(3-methylbut-3-en-1-ynyl)cyclohex-2-enone 
• 1449580-68-0 C₁₄H₁₉FO₃ 
• 1449580-69-1 C₁₄H₁₉FO₃ 
• 60417-94-9 5,5-dimethyl-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one 

Relevant articles and documents

Enantioselective synthesis of the tricyclic core of (+)-strigol

An enantioselective synthesis of the tricyclic core structure of (+)-strigol, a potent seed germination stimulant for root parasitic weeds, has been achieved from 2-iodo-4,4-dimethyl-2-cyclohexen-1-one in 14 steps. The key steps include a CBS reduction of an iodo enone to obtain a cyclohexenol derivative of high enantiomeric excess, regioselective epoxide ring opening with a Grignard reagent in a low-polarity solvent, highly diastereoselective addition of vinyllithium to a ketone, and Lewis acid-promoted installation an acetate unit onto a bicyclic allylic acetate intermediate.

General Access to Concave-Substituted cis-Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A

The evolution of a strategy to access the family of rearranged spongian diterpenoids harboring a concave-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-one fragment is described. The approach involves late-stage fragment coupling of a tertiary-carbon radical and an electron-deficient double bond to form vicinal quaternary and tertiary stereocenters with high fidelity. A stereoselective Mukaiyama hydration is the key step in the subsequent elaboration of the cis-2,8-dioxabicyclo[3.3.0]octan-3-one moiety. This strategy was utilized in enantioselective total syntheses of (-)-macfarlandin C and (+)-dendrillolide A. An efficient construction of enantiopure tetramethyloctahydronaphthalenes was developed during the construction of (-)-macfarlandin C.

Pd-catalyzed regioselective C?H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary

A Pd-catalyzed regioselective C?H alkenylation of allylic alcohols with electron-deficient alkenes has been developed. The key to success is the introduction of bidentately coordinating phenanthroline directing group, which enables the otherwise challenging and regioselective C?H activation at the proximal alkenyl C?H bonds over the conceivably competitive allylic C?O bond activation. The same Pd/phenanthroline system is efficient for the C?H alkynylation of allylic alcohols with alkynyl bromides.