55320-40-6

Basic information

• Product Name: bicyclo[2.2.2]oct-2-en-7-ol
• Synonyms: bicyclo[2.2.2]oct-2-en-7-ol
• CAS NO: 55320-40-6
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18
• Mol File: 55320-40-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 205.4°C at 760 mmHg
• Flash Point: 73.1°C
• Appearance: /
• Density: 1.096g/cm³
• Vapor Pressure: 0.0597mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: bicyclo[2.2.2]oct-2-en-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: bicyclo[2.2.2]oct-2-en-7-ol(55320-40-6)
• EPA Substance Registry System: bicyclo[2.2.2]oct-2-en-7-ol(55320-40-6)

Safety Data

• Hazardous Substances Data: 55320-40-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12O/c9-8-5-6-1-3-7(8)4-2-6/h1,3,6-9H,2,4-5H2

Upstream product

• 34020-37-6 endo-bicyclo<2.2.2>oct-5-en-2-yl acetate 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 1165952-91-9 cyclohexa-1,3-diene 
• 64694-57-1 3,4,4a,5,6,7,8,8a-octahydro-3,7-cyclo-cinnoline 
• 108-05-4 vinyl acetate 
• 6336-45-4 vinylboronic acid dibutyl ester 
• 68908-13-4 bicyclo[2.2.2]oct-5-en-2-one 
• 16196-15-9 (1R,4R)-(+)-bicyclo<2.2.2>oct-5-en-2-one 
• 1614-89-7 exo hydroxy-6 tricyclo<3.2.1.0^2.7>octane 
• 1614-89-7 endo hydroxy-6 tricyclo<3.2.1.0^2.7>octane 
• 486-25-9 9-fluorenone 
• 6688-07-9 5-hydroxybicyclo[2.2.2]oct-2-ene 
• 556-91-2 aluminum tri-tert-butoxide 
• 71-43-2 benzene 

Downstream Products

• 6688-07-9 hydroxy-5 exo bicyclo<2.2.2>octene-2 
• 34020-37-6 exo-Bicyclo<2.2.2>octen-(5)-yl-(2)-acetat 
• 42587-61-1 bicyclo<2.2.2>oct-5-en-2-one p-toluenesulfonylhydrazone 
• 500-23-2 bicyclo[2.2.2]octa-2,5-diene 
• 931-64-6 norbornene 
• 56206-38-3 5-exo-methoxybicyclo[2.2.2]oct-5-en-2-one 
• 98173-21-8 Phthalic acid mono-bicyclo[2.2.2]oct-5-en-2-yl ester 

Relevant articles and documents

Alkylhalovinylboranes: a new class of Diels-Alder dienophiles

The Diels-Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although endo/exo selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group on the boron atom by a halogen increases the dienophilicity considerably.

A facile microwave-assisted Diels-Alder reaction of vinylboronates

The Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.

4S,5S-[Bis(carbethoxy)]-2-ethenyl-1,3,2-dioxaborolane: A novel enantioselective dienophile

The novel chiral vinyl boronate (+)-1 was utilized as a dienophile in a series of [4+2] cycloadditions. The intermediate cyclized products obtained were oxidized directly (H2O2, NaOH). The resulting alcohols displayed enantiomeric excesses of 7-33%. A slight preference for the endo configuration was observed, in agreement with previous results.