5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

Base Information

Chemical Name:5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
CAS No.:714964-21-3
Molecular Formula:C₁₉H₂₃NO₃
Molecular Weight:313.397
Hs Code.:

Synonyms:5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

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Chemical Property of 5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

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Technology Process of 5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

There total 7 articles about 5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.7%

: 714964-20-2
4-tert-butyl-5-[3-(1-cyanoethenyl)phenyl]-3,3-dimethyl-2,3-dihydrofuran

: 714964-21-3
5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

Guidance literature:: With oxygen; 5,15,10,20-tetraphenylporphyrin; In dichloromethane; at -78 ℃; Irradiation;
DOI:10.1016/j.tet.2005.07.081

Reference yield:

: 866129-66-0
5-(3-bromophenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran

: 714964-21-3
5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 6 steps

1.1: butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 96.3 percent / tetrahydrofuran; hexane / 0.5 h

2.1: 96 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h

3.1: 94.3 percent / CBr₄; PPh₃ / tetrahydrofuran / 0.5 h / 20 °C

4.1: 76.4 percent / tetra-n-butylammonium hydrogen sulfate / tetrahydrofuran; H₂O / 28 h / Heating

5.1: 81.3 percent / K₂CO₃; Bu₄NI / toluene / 0.25 h / 80 °C

6.1: 89.7 percent / oxygen; tetraphenylporphine / CH₂Cl₂ / -78 °C / Irradiation

With sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; oxygen; tetra(n-butyl)ammonium hydrogensulfate; 5,15,10,20-tetraphenylporphyrin; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2005.07.081

Reference yield:

: 866129-69-3
4-tert-butyl-5-(3-formylphenyl)-3,3-dimethyl-2,3-dihydrofuran

: 714964-21-3
5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h

2: 94.3 percent / CBr₄; PPh₃ / tetrahydrofuran / 0.5 h / 20 °C

3: 76.4 percent / tetra-n-butylammonium hydrogen sulfate / tetrahydrofuran; H₂O / 28 h / Heating

4: 81.3 percent / K₂CO₃; Bu₄NI / toluene / 0.25 h / 80 °C

5: 89.7 percent / oxygen; tetraphenylporphine / CH₂Cl₂ / -78 °C / Irradiation

With sodium tetrahydroborate; carbon tetrabromide; oxygen; tetra(n-butyl)ammonium hydrogensulfate; 5,15,10,20-tetraphenylporphyrin; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2005.07.081