Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 4-methoxy-

Base Information

• Chemical Name: Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 4-methoxy-
• CAS No.: 1199-31-1
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• DSSTox Substance ID: DTXSID50481880
• Nikkaji Number: J2.108.087J
• Mol file: 1199-31-1.mol

Synonyms:1199-31-1;Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 4-methoxy-;1-Cyano-5-methoxybenzocyclobutene;SCHEMBL3161060;DTXSID50481880;DQCTUNOBJMHLHP-UHFFFAOYSA-N;4-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

Chemical Property of Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 4-methoxy-

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 217

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC2=C(CC2C#N)C=C1

Refernces

TANDEM ELECTROCYCLIC-SIGMATROPIC REACTION OF BENZOCYCLOBUTENES. 2. A NEW ROUTE TO ISOCHROMAN-3-ONE-4-SPIRO-1'-CYCLOALK-3'-ENES

10.1016/S0040-4039(00)84151-9

The research describes a novel synthetic methodology for constructing spiro-fused isochroman-3-one derivatives, which are potentially useful as synthons for natural products such as Amaryllidaceae alkaloids. The study focuses on the tandem electrocyclic-sigmatropic reaction of benzocyclobutenylspirolactones, derived from 1-cyano-5-methoxybenzocyclobutene, to yield isochroman-3-one-4-spiro-1'-cycloalk-3'-enes in good yields. The process involves a series of chemical reactions, including alkylation, acid hydrolysis, basic hydrolysis, and acid treatment, utilizing chemicals such as LDA (lithium diisopropylamide), vinylmagnesium bromide, and various dioxolane derivatives. The conclusions of the research highlight the efficiency of this method in providing a unique route to合成spirocyclic compounds, with applications in the synthesis of Amaryllidaceae alkaloids currently underway.