(1R,3aR,8aS)-3a,6-Dimethyl-1-[(2R)-6-methyl-3-oxoheptan-2-yl]-2,3,3a,7,8,8a-hexahydroazulen-4(1H)-one

Base Information

Chemical Name:(1R,3aR,8aS)-3a,6-Dimethyl-1-[(2R)-6-methyl-3-oxoheptan-2-yl]-2,3,3a,7,8,8a-hexahydroazulen-4(1H)-one
CAS No.:116428-62-7
Molecular Formula:C₂₀H₃₂O₂
Molecular Weight:304.473
Hs Code.:

Synonyms:4(1H)-Azulenone,1-(1,5-dimethyl-3-oxohexyl)-2,3,3a,7,8,8a-hexahydro-3a,6-dimethyl-, [1R-[1a(R*),3ab,8aa]]-; (-)-Reiswigin A; Reiswigin A

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Chemical Property of (1R,3aR,8aS)-3a,6-Dimethyl-1-[(2R)-6-methyl-3-oxoheptan-2-yl]-2,3,3a,7,8,8a-hexahydroazulen-4(1H)-one

Chemical Property:

Vapor Pressure:0mmHg at 25°C
Boiling Point:412.15°C at 760 mmHg
Flash Point:154.233°C
Density:0.972g/cm³

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (1R,3aR,8aS)-3a,6-Dimethyl-1-[(2R)-6-methyl-3-oxoheptan-2-yl]-2,3,3a,7,8,8a-hexahydroazulen-4(1H)-one

There total 29 articles about (1R,3aR,8aS)-3a,6-Dimethyl-1-[(2R)-6-methyl-3-oxoheptan-2-yl]-2,3,3a,7,8,8a-hexahydroazulen-4(1H)-one 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: 85.0%

: {2-[(1R,2R,3R)-3-((R)-1,5-Dimethyl-3-oxo-hexyl)-1-methyl-2-(3-oxo-butyl)-cyclopentyl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

: 116428-62-7
(-)-Reiswigin A

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 24h; Ambient temperature;
DOI:10.1016/0040-4039(94)80021-9

Reference yield:

: 162210-61-9
(R)-1-Iodo-2,6-dimethyl-heptan-4-one

: 116428-62-7
(-)-Reiswigin A

Guidance literature:: Multi-step reaction with 16 steps

1: 88 percent / toluene / 10 h / 110 °C

2: 82 percent / PTSA / benzene / 48 h / 80 °C

3: 62 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 3 h, room t., 1 h

4: 95 percent / K₂CO₃ / methanol / 5 h / 40 °C

5: 93 percent / EtCOOH / 4 h / 120 °C

6: 92 percent / Li, NH₃ / tetrahydrofuran; ethanol / 0.5 h / -78 °C

7: 95 percent / imidazole / dimethylformamide / 0 deg C, 2 h and room t., 5 h

8: 92 percent / Ph-OH / 3 h / 130 °C

9: 87 percent / H₂ / PtO₂ / ethanol; triethylamine / 3 h / 3102.9 Torr / Ambient temperature

10: 92 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

11: 96 percent / pyridine / CHCl₃ / 18 h / Ambient temperature

12: 92 percent / KHMDS / tetrahydrofuran / -78 deg C, 2 h and -40 deg C, 3 h

13: 90 percent / tetrahydrofuran / -78 deg C, 2 h and -20 deg C, 1 h

14: 100 percent / cc-HCl / methanol / 1 h / 60 °C

15: 92 percent / PCC / CH₂Cl₂ / 3 h / Ambient temperature

16: 85 percent / DBU / acetonitrile / 24 h / Ambient temperature

With pyridine; 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; ammonia; hydrogen; lithium; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; hydrogenchloride; platinum(IV) oxide; propionic acid; phenol; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; chloroform; triethylamine; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1016/0040-4039(94)80021-9

Reference yield:

: (R)-2-Hydroxy-5-iodo-2-isobutyl-4-methyl-pentanenitrile

: 116428-62-7
(-)-Reiswigin A

Guidance literature:: Multi-step reaction with 17 steps

1: 0.5N NaOH / diethyl ether / 0.17 h

2: 88 percent / toluene / 10 h / 110 °C

3: 82 percent / PTSA / benzene / 48 h / 80 °C

4: 62 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 3 h, room t., 1 h

5: 95 percent / K₂CO₃ / methanol / 5 h / 40 °C

6: 93 percent / EtCOOH / 4 h / 120 °C

7: 92 percent / Li, NH₃ / tetrahydrofuran; ethanol / 0.5 h / -78 °C

8: 95 percent / imidazole / dimethylformamide / 0 deg C, 2 h and room t., 5 h

9: 92 percent / Ph-OH / 3 h / 130 °C

10: 87 percent / H₂ / PtO₂ / ethanol; triethylamine / 3 h / 3102.9 Torr / Ambient temperature

11: 92 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

12: 96 percent / pyridine / CHCl₃ / 18 h / Ambient temperature

13: 92 percent / KHMDS / tetrahydrofuran / -78 deg C, 2 h and -40 deg C, 3 h

14: 90 percent / tetrahydrofuran / -78 deg C, 2 h and -20 deg C, 1 h

15: 100 percent / cc-HCl / methanol / 1 h / 60 °C

16: 92 percent / PCC / CH₂Cl₂ / 3 h / Ambient temperature

17: 85 percent / DBU / acetonitrile / 24 h / Ambient temperature

With pyridine; 1H-imidazole; sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; ammonia; hydrogen; lithium; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; hydrogenchloride; platinum(IV) oxide; propionic acid; phenol; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; chloroform; triethylamine; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1016/0040-4039(94)80021-9