2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

Base Information

Chemical Name:2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine
CAS No.:143951-12-6
Molecular Formula:C₂₃H₂₇NO
Molecular Weight:333.473
Hs Code.:

Synonyms:2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

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Chemical Property of 2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

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Technology Process of 2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

There total 7 articles about 2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine 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: 70.0%

: 143951-09-1
2-phenyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

: 106-95-6
allyl bromide

: 143951-12-6
2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 60 ℃; for 4h;
DOI:10.1016/0223-5234(92)90150-Y

Reference yield:

: 116708-14-6
1-Benzyl-3,4-dimethyl-1,2,5,6-tetrahydro-pyridine-2-carbonitrile

: 143951-12-6
2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, -60 deg C, 15 min, 2.) THF, from -60 deg C to RT, 2 h

2: 46 percent / tetrahydrofuran / 1 h / 0 °C

3: 55 percent / 48percent aq. HBr / 21 h / 120 °C

4: 99 percent / H₂ / Pd(OH)2/C / methanol / 4 h

5: 70 percent / NaHCO₃ / dimethylformamide / 4 h / 60 °C

With hydrogen bromide; hydrogen; sodium hydrogencarbonate; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/0223-5234(92)90150-Y

Reference yield:

: 116708-12-4
1-benzyl-2-cyano-3,4-dimethyl-2-(p-methoxybenzyl)-1,2,5,6-tetrahydropyridine

: 143951-12-6
2-phenyl-3-allyl-6,11α-dimethyl-8-hydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

Guidance literature:: Multi-step reaction with 4 steps

1: 46 percent / tetrahydrofuran / 1 h / 0 °C

2: 55 percent / 48percent aq. HBr / 21 h / 120 °C

3: 99 percent / H₂ / Pd(OH)2/C / methanol / 4 h

4: 70 percent / NaHCO₃ / dimethylformamide / 4 h / 60 °C

With hydrogen bromide; hydrogen; sodium hydrogencarbonate; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/0223-5234(92)90150-Y