185303-22-4

Basic information

• Product Name: Ethanone, 1-(1R,2R,4R)-bicyclo[2.2.2]oct-5-en-2-yl-, rel- (9CI)
• Synonyms: Ethanone, 1-(1R,2R,4R)-bicyclo[2.2.2]oct-5-en-2-yl-, rel- (9CI)
• CAS NO: 185303-22-4
• Molecular Formula: C10H14O
• Molecular Weight: 150.21756
• Product Categories: ACETYLGROUP
• Mol File: 185303-22-4.mol
• Article Data: 38

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 1-(1R,2R,4R)-bicyclo[2.2.2]oct-5-en-2-yl-, rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(1R,2R,4R)-bicyclo[2.2.2]oct-5-en-2-yl-, rel- (9CI)(185303-22-4)
• EPA Substance Registry System: Ethanone, 1-(1R,2R,4R)-bicyclo[2.2.2]oct-5-en-2-yl-, rel- (9CI)(185303-22-4)

Safety Data

• Hazardous Substances Data: 185303-22-4(Hazardous Substances Data)

Upstream product

• 78-94-4 methyl vinyl ketone 
• 1165952-91-9 cyclohexa-1,3-diene 
• 823-76-7 Cyclohexyl methyl ketone 
• 292638-85-8 acrylic acid methyl ester 
• 54515-89-8 (+)-(1S,2S,4S)-bicyclo[2.2.2]oct-5-en-2-yl methanol 
• 211636-24-7 (1S,2S,4S)-Bicyclo[2.2.2]oct-5-ene-2-carbaldehyde 
• 20507-57-7 (-)-(1S,2S,4S)-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid 
• 110-83-8 cyclohexene 
• 107-02-8 acrolein 

Downstream Products

• 2716-23-6 bicyclo[2.2.2]octan-2-one 
• 23735-46-8 Bicyclo<2.2.2>oct-2-ylmethylketon 

Relevant articles and documents

A Bidentate Iodine(III)-Based Halogen-Bond Donor as a Powerful Organocatalyst**

In contrast to iodine(I)-based halogen bond donors, iodine(III)-derived ones have only been used as Lewis acidic organocatalysts in a handful of examples, and in all cases they acted in a monodentate fashion. Herein, we report the first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro-Michael addition reaction as well as in a Diels–Alder reaction that had not been activated by noncovalent organocatalysts before. In all cases, the performance of this bidentate XB donor distinctly surpassed the one of arguably the currently strongest iodine(I)-based organocatalyst. Bidentate coordination to the substrate was corroborated by a structural analysis and by DFT calculations of the transition states. Overall, the catalytic activity of the bis(iodolium) system approaches that of strong Lewis acids like BF3.

STRONGLY LEWIS ACIDIC METAL-ORGANIC FRAMEWORKS FOR CONTINUOUS FLOW CATALYSIS

Lewis acidic metal-organic framework (MOF) materials comprising triflate-coordinated metal nodes are described. The materials can be used as heterogenous catalysts in a wide range of organic group transformations, including Diels-Alder reactions, epoxide-ring opening reactions, Friedel-Crafts acylation reactions and alkene hydroalkoxylation reactions. The MOFs can also be prepared with metallated organic bridging ligands to provide heterogenous catalysts for tandem reactions and/or prepared as composites with support particles for use in columns of continuous flow reactor systems. Methods of preparing and using the MOF materials and their composites are also described.

Iodine-Catalyzed Diels-Alder Reactions

The Diels-Alder cycloaddition is the most popular pericyclic reaction with numerous applications in synthesis and catalysis. We now demonstrate that we can perform this reaction under mild and metal-free conditions relying on molecular iodine as the catalyst. Cycloadditions with cyclohexadiene, cyclopentadiene, or isoprene with various dienophiles can be performed typically within minutes in moderate to good yields and high endo selectivity. The mechanistic studies including kinetic and DFT investigations clearly indicate a halogen-bond activation and rule out other modes of activation. Furthermore, iodine performs equally well as typical metallic Lewis acids like AlCl3, SnCl4, or TiCl4.