2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole

Base Information

Chemical Name:2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole
CAS No.:80516-04-7
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole

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Chemical Property of 2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole

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Technology Process of 2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole

There total 12 articles about 2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole 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: 77.0%

: 80516-02-5
2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-7-bromo-2,3,3a,4,5,6,7,7a-octahydroindole

: 80516-04-7
2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole

Guidance literature:: With azobisisobutyronitrile; tri-n-butyl-tin hydride; In benzene; for 1h; Heating;
DOI:10.1021/jo00346a028

Reference yield:

: 91-16-7
1,2-dimethoxybenzene

: 80516-04-7
2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole

Guidance literature:: Multi-step reaction with 12 steps

1: 66 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 16 h / Heating

3: 89 percent / NaBH₄ / ethanol / 12 h / -20 °C

4: 76 percent / pyridine / 18 h / Ambient temperature

5: 1.) lithium isopropylcyclohexylamide, HMPA, 2.) tert-butyldimethylchlorosilane / 1.) THF, -78 deg C, 5 min, 2.) reflux, 3 h

6: 1.) SOCl₂, 2.) NH₂OH*HCl, Na₂CO₃ / 1.) benzene, DMF, reflux, 2 h, 2.) diethyl ether

7: 82.5 percent / tetrapropylammonium periodate / CHCl₃; dimethylformamide

8: 100 percent / toluene / 0.33 h / Heating

9: 78 percent / Na₂CO₃, TiCl₃ / H₂O; methanol / 18 h / Ambient temperature

10: 87 percent / DME-H₂O, N-bromosuccinimide / 12 h / 0 °C

11: 98 percent / pyridine / 2 h

12: 77 percent / α,α'-azobis(isobutyronitrile) (AIBN), tri-n-butyltin hydride / benzene / 1 h / Heating

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; Perbenzoic acid; titanium(III) chloride; tetrapropylammonium periodate; DME-H₂O; azobisisobutyronitrile; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium carbonate; lithium cyclohexylisopropylamide; tert-butyldimethylsilyl chloride; In pyridine; methanol; tetrachloromethane; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo00346a028

Reference yield:

: 20036-53-7
3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one

: 80516-04-7
2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-acetoxy-2,3,3a,4,5,6,7,7a-octahydroindole

Guidance literature:: Multi-step reaction with 10 steps

1: 89 percent / NaBH₄ / ethanol / 12 h / -20 °C

2: 76 percent / pyridine / 18 h / Ambient temperature

3: 1.) lithium isopropylcyclohexylamide, HMPA, 2.) tert-butyldimethylchlorosilane / 1.) THF, -78 deg C, 5 min, 2.) reflux, 3 h

4: 1.) SOCl₂, 2.) NH₂OH*HCl, Na₂CO₃ / 1.) benzene, DMF, reflux, 2 h, 2.) diethyl ether

5: 82.5 percent / tetrapropylammonium periodate / CHCl₃; dimethylformamide

6: 100 percent / toluene / 0.33 h / Heating

7: 78 percent / Na₂CO₃, TiCl₃ / H₂O; methanol / 18 h / Ambient temperature

8: 87 percent / DME-H₂O, N-bromosuccinimide / 12 h / 0 °C

9: 98 percent / pyridine / 2 h

10: 77 percent / α,α'-azobis(isobutyronitrile) (AIBN), tri-n-butyltin hydride / benzene / 1 h / Heating

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; titanium(III) chloride; tetrapropylammonium periodate; DME-H₂O; azobisisobutyronitrile; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium carbonate; lithium cyclohexylisopropylamide; tert-butyldimethylsilyl chloride; In pyridine; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo00346a028