2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine

Base Information

Chemical Name:2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine
CAS No.:610300-90-8
Molecular Formula:C₃₂H₃₂NOP
Molecular Weight:477.586
Hs Code.:

Synonyms:2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine

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Chemical Property of 2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine

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Technology Process of 2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine

There total 8 articles about 2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine 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: 82.0%

: 610300-90-8
2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine

Guidance literature:

Reference yield: 78.0%

: 4559-70-0
Diphenylphosphine oxide

: 610300-86-2
2-phenyl-6-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]pyridine

: 610300-90-8
2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine

Guidance literature:: With potassium tert-butylate; In dimethyl sulfoxide; at 70 ℃; for 12h;
DOI:10.1002/anie.200351936

Reference yield:

: 38651-65-9
(1R,5S)-(+)-nopinone

: 610300-90-8
2-[(1S,2R,3S,5R)-3-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-6-phenylpyridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 92 percent / tetrahydrofuran / 14 h / 0 °C

2.1: n-BuLi; ZnBr₂ / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

2.2: 70 percent / dppf / Pd(dba)2 / hexane; tetrahydrofuran / 16 h / 70 °C

3.1: 91 percent / Na₂CO₃; H₂O / Pd(PPh₃)4 / toluene; methanol / 16 h / 85 °C

4.1: 78 percent / t-BuOK / dimethylsulfoxide / 15 h / 70 °C

With n-butyllithium; potassium tert-butylate; water; sodium carbonate; zinc dibromide; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dimethyl sulfoxide; toluene; 2.2: Negishi cross-coupling / 3.1: Suzuki cross-coupling;
DOI:10.1021/jo030383u