(4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde

Base Information

Chemical Name:(4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde
CAS No.:1438285-76-7
Molecular Formula:C₂₄H₂₈N₂O
Molecular Weight:360.499
Hs Code.:

Synonyms:(4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde

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Chemical Property of (4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde

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Technology Process of (4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde

There total 13 articles about (4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde 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: 96.0%

: 1438285-75-6
((4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthrolin-9-yl)methanol

: 1438285-76-7
(4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 23 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/jo400695c

Reference yield:

: 1225377-71-8
2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

: 1438285-76-7
(4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: dicarbonylcyclopentadienylcobalt / tetrahydrofuran / 30 h / 140 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / 1,4-dioxane / 0.5 h / 23 °C / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 0.5 h / 23 °C / Inert atmosphere

With dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo400695c

Reference yield:

: 89-82-7,90449-51-7
pulegone

: 1438285-76-7
(4aR,5S,10bR,12R)-1-benzyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline-9-carbaldehyde

Guidance literature:: Multi-step reaction with 13 steps

1.1: lithium hydroxide; water / methanol / 23 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 66 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.08 h / 0 °C / Inert atmosphere

3.2: 70 h / 23 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 11 h / -78 - 23 °C / Inert atmosphere

5.1: n-butyllithium / diethyl ether; hexane / 0.68 h / -78 °C / Inert atmosphere

5.2: 0.55 h / -78 °C / Inert atmosphere

6.1: tetrahydrofuran; toluene / 0.58 h / 23 °C / Inert atmosphere

7.1: magnesium(II) perchlorate / 0.5 h / 23 °C / Inert atmosphere

8.1: copper(l) chloride / tetrahydrofuran / 0.5 h / 80 °C / Inert atmosphere

9.1: potassium carbonate / methanol / 7 h / 23 °C / Inert atmosphere

10.1: triphenylphosphine; 1H-imidazole / tetrachloromethane / 15 h / 77 °C / Inert atmosphere

11.1: dicarbonylcyclopentadienylcobalt / tetrahydrofuran / 30 h / 140 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / 1,4-dioxane / 0.5 h / 23 °C / Inert atmosphere

13.1: Dess-Martin periodane / dichloromethane / 0.5 h / 23 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; magnesium(II) perchlorate; dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; copper(l) chloride; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jo400695c