(-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole

Base Information

Chemical Name:(-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole
CAS No.:865769-28-4
Molecular Formula:C₁₈H₂₁NO
Molecular Weight:267.371
Hs Code.:

Synonyms:(-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole

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Chemical Property of (-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole

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Technology Process of (-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole

There total 6 articles about (-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole 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: 83.0%

: 865769-22-8
(-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

: 865769-28-4
(-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole

Guidance literature:: With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃;
DOI:10.1002/ejoc.200500144

Reference yield:

: myrtenic acid chloride

: 865769-28-4
(-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / Et₃N / dioxane / 10 °C

2: 83 percent / Et₃N; p-TsCl / CH₂Cl₂ / 20 °C

With triethylamine; p-toluenesulfonyl chloride; In 1,4-dioxane; dichloromethane;
DOI:10.1002/ejoc.200500144

Reference yield:

: 564-94-3,18486-69-6
myrtenal

: 865769-28-4
(-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole

Guidance literature:: Multi-step reaction with 6 steps

1: NH₂OH*HCl; NaHCO₃ / ethanol; H₂O / 20 h / Heating

2: 67.9 g / Ac₂O; NaOAc / 120 h / 100 °C

3: 99 percent / aq. NaOH; aq. H₂O₂ / 96 h / Heating

4: (COCl)2; DMF / toluene / 20 °C

5: 80 percent / Et₃N / dioxane / 10 °C

6: 83 percent / Et₃N; p-TsCl / CH₂Cl₂ / 20 °C

With sodium hydroxide; oxalyl dichloride; hydroxylamine hydrochloride; dihydrogen peroxide; sodium acetate; acetic anhydride; sodium hydrogencarbonate; triethylamine; N,N-dimethyl-formamide; p-toluenesulfonyl chloride; In 1,4-dioxane; ethanol; dichloromethane; water; toluene;
DOI:10.1002/ejoc.200500144