(2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester
CAS No.:161693-60-3
Molecular Formula:C₂₃H₃₁NO₂
Molecular Weight:353.505
Hs Code.:

Synonyms:(2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

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Chemical Property of (2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

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Technology Process of (2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

There total 15 articles about (2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester 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: 92.0%

: 161693-59-0
(2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester

: 161693-60-3
(2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

Guidance literature:: With dihydrogen peroxide; In tetrahydrofuran;
DOI:10.1021/jo00109a006

Reference yield:

: 161693-50-1
(S)-2-Pent-4-enyl-2,3-dihydro-1H-pyridin-4-one

: 161693-60-3
(2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 93 percent / n-BuLi

2: 79 percent / CuBr, BF₃*OEt₂ / -78 °C

3: 88 percent / NaIO₄ / OsO₄

4: 92 percent / TsOH / benzene / 52 °C

6: 86 percent / Bu₃N, HCO₂H / (Ph₃P)Pd(OAc)2

7: 87 percent / aq. KOH / propan-2-ol / 144 h / Heating

8: H₂ / 5percent Pt/C / ethanol

9: H₂ / Pd(OH)2 / ethanol

10: NaOH

11: K₂CO₃ / methanol

12: 79 percent / Bu₃P / CH₂Cl₂

13: 92 percent / 30percent aq. H₂O₂ / tetrahydrofuran

With potassium hydroxide; sodium hydroxide; sodium periodate; n-butyllithium; formic acid; tributyl-amine; tributylphosphine; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; copper(I) bromide; palladium dihydroxide; osmium(VIII) oxide; platinum on activated charcoal; Pd(PPh₃)(OAc)2; In tetrahydrofuran; methanol; ethanol; dichloromethane; isopropyl alcohol; benzene;
DOI:10.1021/jo00109a006

Reference yield:

: 161755-27-7
(S)-4-Oxo-2-pent-4-enyl-3,4-dihydro-2H-pyridine-1-carboxylic acid phenyl ester

: 161693-60-3
(2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 79 percent / CuBr, BF₃*OEt₂ / -78 °C

2: 88 percent / NaIO₄ / OsO₄

3: 92 percent / TsOH / benzene / 52 °C

5: 86 percent / Bu₃N, HCO₂H / (Ph₃P)Pd(OAc)2

6: 87 percent / aq. KOH / propan-2-ol / 144 h / Heating

7: H₂ / 5percent Pt/C / ethanol

8: H₂ / Pd(OH)2 / ethanol

9: NaOH

10: K₂CO₃ / methanol

11: 79 percent / Bu₃P / CH₂Cl₂

12: 92 percent / 30percent aq. H₂O₂ / tetrahydrofuran

With potassium hydroxide; sodium hydroxide; sodium periodate; formic acid; tributyl-amine; tributylphosphine; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; copper(I) bromide; palladium dihydroxide; osmium(VIII) oxide; platinum on activated charcoal; Pd(PPh₃)(OAc)2; In tetrahydrofuran; methanol; ethanol; dichloromethane; isopropyl alcohol; benzene;
DOI:10.1021/jo00109a006