32222-49-4

Basic information

• Product Name: Bicyclo[3.2.1]oct-3-en-2-ol, endo-
• CAS NO: 32222-49-4
• Molecular Formula: C8H12O
• Mol File: 32222-49-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Bicyclo[3.2.1]oct-3-en-2-ol, endo-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.2.1]oct-3-en-2-ol, endo-(32222-49-4)
• EPA Substance Registry System: Bicyclo[3.2.1]oct-3-en-2-ol, endo-(32222-49-4)

Safety Data

• Hazardous Substances Data: 32222-49-4(Hazardous Substances Data)

Upstream product

• 1070-68-4 5-methyloctanoic acid 
• 84143-97-5 (-)-exo-bicyclo<3.2.1>oct-3-en-2-amine 
• 20507-56-6 bicyclo<2.2.2>oct-5-ene-2-exo-carboxylic acid 
• 4802-43-1 axial-Bicyclo<3.2.1>octen-(3)-ol-(2) 
• 497-38-1 2-norbornanone 
• 57722-40-4 2-trimethylsilyloxybicyclo<2.2.1>hept-2-ene 
• 99957-00-3 Trimethyl-((1S,2S,4S,5R)-tricyclo[3.2.1.0^2,4]oct-2-yloxy)-silane 
• 3212-77-9 bicyclo<3.2.1>oct-3-en-2-one 
• 39762-77-1 endo-bicyclo<3.2.1.>oct-3-en-2-yl acetate 
• 3212-77-9 2-Oxobicyclo<3.2.1>oct-3-ene 

Downstream Products

• 237736-41-3 (-)-endo-Bicyclo[3.2.1]oct-3-en-2-ol 
• 237736-40-2 (+)-endo-Bicyclo[3.2.1]oct-3-en-2-ol 
• 79027-20-6 exo-bicyclo<3.2.1>oct-3-en-2-yl acetate 
• 4802-43-1 exo-bicyclo<3.2.1>oct-3-en-2-ol 
• 32222-49-4 endo-bicyclo<3.2.1>oct-3-en-2-ol 
• 319906-87-1 (-)-(1R,5S)-4-Benzyloxymethylbicyclo[3.2.1]oct-3-en-2-one 
• 319906-82-6 (1R,4S,5S)-4-Benzyloxymethyl-bicyclo[3.2.1]octan-2-one 
• 319906-88-2 (-)-(1R,4R,5S)-4-Benzyloxymethylbicyclo[3.2.1]octan-2-one 
• 319906-86-0 (+)-(1R,2S,5R)-2-Benzyloxymethylbicyclo[3.2.1]oct-3-en-2-ol 
• 237752-68-0 (+)-4-Acetoxybicyclo[3.2.1]oct-2-ene 
• 88158-53-6 endo-bicyclo<3.2.1>oct-3-en-2-yl mesitoate 

Relevant articles and documents

ORBITAL CONTROL OF STEREOCHEMISTRY IN ACID-CATALYSED ADDITION REACTIONS OF ENDO-TRICYCLO2.4>OCT-6-ENE

The reaction of endo-tricyclo2.4>oct-6-ene 1 with methanol in the presence of catalytic amounts of toluene-p-sulphonic acid has been shown to give 2-exo- and endo-methoxybicyclooct-3-ene (2c) and (2d) and 2-endo-methoxybicyclooct-6-ene (13).The formation of 2-exo-methoxybicyclooct-3-ene (2c), the major product of reaction, has been probed by deuterium labelling experiments and a series of 6-exo-7-exo-dideuterobicyclooct-3-enes synthesised for (2)H, (1)H and (13)C NMR spectral analysis in order unambiguously to determine the stereochemistry of proton attack on endo-tricyclo2.4>oct-6-ene ( 1).The formation of 2-exo-methoxybicyclooct-3-ene (2c) has been determined to involve corner protonation of the cyclopropyl moiety and skeletal rearrangement to an allylic cation with a small but measurable memory effect.

Diastereodivergent synthesis of the C9-cyclopentanone chiral building blocks

Diastereodivergent synthesis the C9-cyclopentanone chiral building block, serving as the non-tryptamine moiety of the Corynanthe type indole alkaloids and the related natural products, and its diastereomer has been developed from racemic norcamphor by employing lipase-mediated resolution via an allylic acetate intermediate having a bicyclo[3.2.1]octane framework. A potential of the latter diastereomer has been demonstrated by its conversion into (-)-semburin, a monoterpene isolated from Swertia japonica previously and obtained from the C9-block.

Alkylation of Allylic Derivatives. 8. Regio- and Stereochemistry of Alkylation of Allylic Carboxylates with Lithium Methylcyanocuprate

Alkylation of 5-methyl-2-cyclohexenyl acetate (1-OAc) with lithium methylcyanocuprate (LiCu(CN)Me) is regiospecific (>90 percent excess γ-alkylation) and sterospecific (>95 percent anti alkylation).In the bicyclooct-3-en-2-yl system (3), alkylation is stereoselective (both isomers give exo alkylation) and regiospecific (excess γ-alkylation).Alkylation of trans-α-methyl-γ-mesitylallyl acetate (8-OAc) with LiCu(CN)Me gives 57 percent α- and 43 percent γ-alkylation as compared to >97 percent α-alkylation with LiCuMe2.Mechanistic implications are discussed.