694-97-3

Basic information

• Product Name: Bicyclo[2.2.1]hept-5-en-2-ol,(1R,2R,4R)-rel-
• Synonyms: 5-Norbornen-2-ol,endo- (8CI); Bicyclo[2.2.1]hept-5-en-2-ol, endo-; NSC 108290; endo-2-Norborn-5-enol; endo-2-Norbornenol; endo-5-Hydroxynorbornene; endo-Bicyclo[2.2.1]hept-5-en-2-ol; endo-Dehydronorborneol
• CAS NO: 694-97-3
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.1537
• Mol File: 694-97-3.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 183.7°Cat760mmHg
• Flash Point: 62°C
• Density: 1.153g/cm³
• CAS DataBase Reference: Bicyclo[2.2.1]hept-5-en-2-ol,(1R,2R,4R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]hept-5-en-2-ol,(1R,2R,4R)-rel-(694-97-3)
• EPA Substance Registry System: Bicyclo[2.2.1]hept-5-en-2-ol,(1R,2R,4R)-rel-(694-97-3)

Safety Data

• Hazardous Substances Data: 694-97-3(Hazardous Substances Data)

Upstream product

• 154278-40-7 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 694-98-4 norborn-5-en-2-one 
• 2890-95-1 5-acetoxynorborn-2-ene 
• 292638-85-8 acrylic acid methyl ester 
• 108-05-4 vinyl acetate 
• 542-92-7 cyclopenta-1,3-diene 
• 18530-45-5 endo-5-Aminobicyclo[2.2.1]hept-2-ene 
• 5257-37-4 (1RS,2SR,4RS)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 7217-01-8 trivinyl borane 
• 236752-25-3 B-vinyl-3,6-dimethylborepane 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 278-06-8 quadricyclo[2.2.1.0.0]heptane 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 1600-27-7 mercury(II) diacetate 

Downstream Products

• 7329-28-4 (1RS,2RS,4SR,5SR,6RS)-3-oxatricyclo<3.2.1.0^2,4>octan-6-ol 
• 694-98-4 norborn-5-en-2-one 
• 497-36-9 (+/-)-endo-2-norborneol 
• 131408-41-8 3-((1R,2S,4R)-Bicyclo[2.2.1]hept-5-en-2-yloxy)-4-methoxy-benzaldehyde 
• 694-97-3 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol 
• 112836-09-6 (1R,2R,4R)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 83679-37-2 (+)-exo-Bicyclo-<2.2.1>-hepten-(5)-yl-(2)-acetat 
• 75-07-0 acetaldehyde 
• 32971-49-6 Bicyclo<2.2.1>hepten-5-en-2-yl-phthalat 
• 497-36-9 endo-norborneol 
• 61277-90-5 exo-norborneol 
• 154278-40-7 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 106928-44-3 (1R,2R,4R)-endo-bicyclo[2.2.1]hept-5-en-2-ol 
• 507235-66-7 (1R,2R,4S)-2-Ethyl-4-(3-trimethylsilanyl-propyl)-cyclopentanol 

Relevant articles and documents

Stereoselective [4+2]-Cycloaddition with Chiral Alkenylboranes

A method for the stereoselective [4+2]-cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N-protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C?B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.

α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights

We have found that α-hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene. When stoichiometric quantities are used, excellent yields are obtained, while catalytic activities are moderate. DFT calculations suggested that the activation of the dienophile occurs by ligand exchange with both functionalities of the α-hydroxyacid.

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.