35447-99-5

Basic information

• Product Name: Bicyclo[4.2.0]octane-1,3,5-triene-7-ol
• Synonyms: 1,2-Ethanobenzene-7-ol;Bicyclo[4.2.0]octa-1(6),2,4-triene-7-ol;Bicyclo[4.2.0]octa-1,3,5-trien-7-ol;Bicyclo[4.2.0]octane-1,3,5-triene-7-ol;1-Hydroxy-Benzocyclobutene;1,2-Dihydrobenzocyclobuten-1-ol;1-Hydroxycyclobutabenzene;Benzocyclobuten-1-ol
• CAS NO: 35447-99-5
• Molecular Formula: C₈H₈O
• Molecular Weight: 120.15
• Mol File: 35447-99-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[4.2.0]octane-1,3,5-triene-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[4.2.0]octane-1,3,5-triene-7-ol(35447-99-5)
• EPA Substance Registry System: Bicyclo[4.2.0]octane-1,3,5-triene-7-ol(35447-99-5)

Safety Data

• Hazardous Substances Data: 35447-99-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 2730, 1981 DOI: 10.1021/jo00326a026

Upstream product

• 694-87-1 benzocyclobutene 
• 21120-91-2 1-bromobenzocyclobutene 
• 3469-06-5 benzocyclobutenone 

Downstream Products

• 36101-20-9 α-hydroxy-o-quinodimethane 
• 89-95-2 2-methyl-benzyl alcohol 
• 130469-01-1 2-Methyl-benzoic acid bicyclo[4.2.0]octa-1,3,5-trien-7-yl ester 
• 101640-51-1 Benzoic acid bicyclo[4.2.0]octa-1,3,5-trien-7-yl ester 
• 101640-50-0 Phenyl-acetic acid bicyclo[4.2.0]octa-1,3,5-trien-7-yl ester 
• 101640-53-3 4-Methoxy-benzoic acid bicyclo[4.2.0]octa-1,3,5-trien-7-yl ester 
• 101640-52-2 4-Nitro-benzoic acid bicyclo[4.2.0]octa-1,3,5-trien-7-yl ester 
• 136715-57-6 2-iodomethylbenzaldehyde 
• 222-93-5 pentaphene 

Relevant articles and documents

DENDRITIC MOLECULAR INTRACELLULAR TRANSPORTERS AND METHODS OF MAKING AND USING SAME

In accordance with the purpose(s) of the invention, as embodied and broadly described herein, the invention, in one aspect, relates to compounds comprising the structure: and at least one guanidinium residue, wherein m is zero or a positive integer. Also disclosed are methods of preparing the disclosed compounds. Also disclosed are methods of intracellular delivery comprising administering the disclosed compounds and compositions to a subject. Also disclosed are pharmaceutical compositions comprising a therapeutically effective amount of one or more compounds or compositions of the invention and a pharmaceutically acceptable carrier. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

A very short synthesis of steroids from 1,3-butadiene and benzocyclobutenes

Lewis acid mediated addition of 1,8-bis(trimethylsilyl)octa-2,6-diene (BISTRO) 1 to succinic anhydride led to spirolactone 2 [(±)-6,9-divinyl-1-oxaspiro[4.4]nonan-2-one]. Methoxycarbonylation followed by stereoselective alkylation by various benzocyclobutenes afforded the substituted benzocyclobutene steroid precursors 5. Thermolysis of 5 gave rise to steroids (±)-6 with a transanti-cis configuration in five steps and in a highly stereoselective manner. Modifications of the sequence allowed the preparation of steroids (±)-11 with trans-anti-trans configuration.

Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites

Benzylic monooxygenation of benzocycloalkenes, 2-4, by enzymes in intact cultures of Pseudomonas putida UV4 yielded exclusively the [R] enantiomers, 6-8, and the derived ketones 10-12; by contrast, biotransformation of benzocyclobutene, 1, yielded both monooxygenation (5 and 9), dioxygenation (13,14 and 15), and trioxygenation (16) products.