2716-23-6

Basic information

• Product Name: Bicyclo[2.2.2]octan-2-one
• Synonyms: Bicyclo[2.2.2]octan-2-one;bicyclo[2.2.2]octan-3-one
• CAS NO: 2716-23-6
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.1803
• Mol File: 2716-23-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 178-179 °C
• Boiling Point: 201.6°Cat760mmHg
• Flash Point: 68.7°C
• Appearance: /
• Density: 1.039g/cm³
• Vapor Pressure: 0.305mmHg at 25°C
• Refractive Index: 1.499
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Bicyclo[2.2.2]octan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.2]octan-2-one(2716-23-6)
• EPA Substance Registry System: Bicyclo[2.2.2]octan-2-one(2716-23-6)

Safety Data

• Hazardous Substances Data: 2716-23-6(Hazardous Substances Data)

Usage

General Description

Bicyclo[2.2.2]octan-2-one is a bicyclic ketone compound with a unique three-dimensional structure. It is often used as a building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and fragrance ingredients. The compound's rigid and strained ring system confers unique reactivity and stereochemistry, making it a valuable precursor in organic chemistry. Bicyclo[2.2.2]octan-2-one can undergo various chemical reactions to functionalize the carbonyl group or modify the ring structure, allowing for the creation of diverse molecular structures with different properties and applications.

InChI:InChI=1/C8H12O/c9-8-5-6-1-3-7(8)4-2-6/h6-7H,1-5H2

Upstream product

• 1165952-91-9 cyclohexa-1,3-diene 
• 76355-29-8 (S)-2-Benzenesulfonyl-bicyclo[2.2.2]octane 
• 68908-13-4 bicyclo[2.2.2]oct-5-en-2-one 
• 18684-63-4 bicyclo<2.2.2>octan-2-ol 
• 6962-73-8 2-chlorobicyclo<2.2.2>oct-5-ene-2-carbonitrile 
• 38258-93-4 5-cyanobicyclo<2.2.2>oct-2-ene 
• 769-44-8 5-nitro-bicyclo[2.2.2]oct-2-ene 
• 931-64-6 norbornene 
• 13398-45-3 (1R,2R,4R)-1-Bicyclo[2.2.2]oct-5-en-2-yl-ethanone 
• 68069-67-0 (1S,4S)-(-)-bicyclo<2.2.2>oct-5-en-2-one 
• 280-33-1 bicyclo[2,2,2]octane 
• 108-24-7 acetic anhydride 
• 66348-59-2 4-hydroxybicyclo<2.2.2>octan-2-one 
• 17082-61-0 1,2-bis(trimethylsiloxy)cyclobutene 

Downstream Products

• 14352-61-5 methyl cyclohexylacetate 
• 2565-96-0 2-Methyl-bicyclo-<2.2.2>-octanol-(2) 
• 73880-51-0 <2-(Dimethylaminomethyl)phenyl>-<(2-hydroxybicyclo<2.2.2>oct-2-yl)methyl>-sulfoxid 
• 40335-86-2 (+)-Bicyclo<2.2.2>octan-2-ol 
• 26051-25-2 3-Methyl-bicyclo<2.2.2>octan-2-on 
• 50682-96-7 3,3-dimethylbicyclo<2.2.2>octan-2-one 
• 52407-99-5 3-p-Fluorbenzylidenbicyclo<2.2.2>octan-2-on 
• 24480-99-7 cyclohex-3-enyl acetaldehyde 
• 40335-86-2 (S)-(+)-bicyclo[2.2.2]octan-2-ol 
• 52455-74-0 3-benzylidene-bicyclo[2.2.2]octan-2-one 
• 6962-74-9 bicyclo[2.2.2]octane-2-carbonitrile 
• 1352952-04-5 C₂₀H₂₉N 
• 1352952-05-6 C₃₀H₅₂N₃PSi 
• 53601-02-8 2-p-Trifluormethylphenylbicyclo<2.2.2>oct-2-en 

Relevant articles and documents

OXIDATIVE DESULFONYLATION. PHENYL VINYL SULFONE AS A KETENE SYNTHETIC EQUIVALENT

α-Sulfonyl carbanions undergo oxidative desulfonylation to form ketones upon treatment with molybdenum peroxide MoO5*Py*HMPA (MoOPH) in THF at -78 deg C.

-

-

NOVEL FUSED BRIDGED BICYCLIC HETEROARYL SUBSTITUTED 6-ALKYLIDENE PENEMS AS POTENT BETA-LACTAMASE INHIBITORS

A compound of formula (I) or formula (Ia) Wherein R1 , Ra, R2, X, R3 , Y1, y2, A, B and C are as defined herein. Also, pharmaceutical compositions comprising such compounds and excipients, methods of treating bacterial infections comprising administering such compounds, methods for making such compounds and hydrates of such compounds.

Thermal reactions of 7-d- and 8-d-bicyclo[4.2.0]oct-2-enes

The gas phase thermal reactions exhibited by bicyclo[4.2.0]oct-2-ene and 7-d and 8-d analogues at 300 °C have been followed kinetically through GC and 2H NMR spectroscopic analyses. In contrast to the pattern of transformations exhibited by bicyclo[3.2.0]hept-2-ene and deuterium-labeled analogues, no reactions initiated by C1-C6 bond cleavage are seen, epimerization at C8 is much faster than [1,3] shifts leading to bicyclo[2.2.2]oct-2-ene, and the ratio of rate constants for [1,3] carbon migration with inversion versus migration with retention is ～1.4. Homolysis of C1-C8 to give a conformationally flexible diradical intermediate having a relatively long lifetime and multiple options for further reaction (re-formation of C1-C8 with or without net epimerization, fragmentation to 1,3-cyclohexadiene and ethylene, migration to the original C3 with inversion or retention) accords well with the observations. Clearly, orbital symmetry control does not govern stereochemistry for the [1,3] sigmatropic carbon shifts. Copyright

Formation of 2,2-disubstituted 1,3-cyclopentanediones from ketals with 1,2-bis(trimethylsilyloxy)cyclobutene

-