(1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol

Base Information

Chemical Name:(1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol
CAS No.:210633-79-7
Molecular Formula:C₂₁H₂₈O₂
Molecular Weight:312.452
Hs Code.:

Synonyms:(1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol

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Chemical Property of (1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol

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Technology Process of (1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol

There total 6 articles about (1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol 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%

: 1826-67-1
vinyl magnesium bromide

: 210633-78-6
(1R,3S,4S)-1,5,5-trimethyl-6-methylene-3-(phenylmethoxy)bicyclo[2.2.2]octan-2-one

: 210633-79-7
(1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1055/s-1998-1801

Reference yield:

: 210633-77-5
(1R,2R,3S,4S)-1,5,5-trimethyl-6-methylene-3-(phenylmethoxy)bicyclo[2.2.2]octan-2-ol

: 210633-79-7
(1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 18 °C

2: 70 percent / tetrahydrofuran / 1 h / 0 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-1998-1801

Reference yield:

: 210633-74-2
(1S,2S,3R,4R)-3-[(4-methoxyphenyl)methoxy]-4,6,6-trimethyl-5-methylenebicyclo[2.2.2]octan-2-ol

: 210633-79-7
(1R,2R,3S,4S)-3-Benzyloxy-1,5,5-trimethyl-6-methylene-2-vinyl-bicyclo[2.2.2]octan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / NaH, Bu₄NI / dimethylformamide / 15 h / 18 °C

2: 97 percent / DDQ, H₂O / CH₂Cl₂ / 0.25 h / 18 °C

3: 98 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 18 °C

4: 70 percent / tetrahydrofuran / 1 h / 0 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; water; tetra-(n-butyl)ammonium iodide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-1998-1801