(4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

Base Information

• Chemical Name: (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline
• CAS No.: 1225377-80-9
• Molecular Formula: C₂₈H₃₆N₂Si
• Molecular Weight: 428.693

Synonyms:(4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

Chemical Property of (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

There total 13 articles about (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 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: 90.0%

chloro-trimethyl-silane (75-77-4) + (4aR,5S,10bR,12R)-1-benzyl-8-ethynyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline (1225377-78-5) → (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline (1225377-80-9)

Guidance literature:

chloro-trimethyl-silane; (4aR,5S,10bR,12R)-1-benzyl-8-ethynyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

With water; ammonium chloride; Inert atmosphere;

DOI:10.1021/ja101956x

Reference yield:

(R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propyl acetate (1225377-59-2) → (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline (1225377-80-9)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: 0.55 h / -78 °C / Inert atmosphere

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

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

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

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

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

7.1: dicarbonylcyclopentadienylcobalt / tetrahydrofuran / 20 h / 140 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 23 °C / Inert atmosphere; Heating

9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.2 h / 0 °C / Inert atmosphere

9.2: 1 h / Inert atmosphere

With 1H-imidazole; n-butyllithium; magnesium(II) perchlorate; dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; potassium carbonate; triphenylphosphine; copper(l) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; toluene;

DOI:10.1021/jo400695c

Reference yield:

2-((1S,2R,3R,5R)-3-ethynyl-2-(3-hydroxypropyl)-3-(benzylamino)-5-methylcyclohexyl)acetonitrile (1225377-69-4) → (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline (1225377-80-9)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: dicarbonylcyclopentadienylcobalt / tetrahydrofuran / 20 h / 140 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 23 °C / Inert atmosphere; Heating

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.2 h / 0 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

With 1H-imidazole; dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane;

DOI:10.1021/jo400695c

upstream raw materials:

chloro-trimethyl-silane

(4aR,5S,10bR,12R)-1-benzyl-8-ethynyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

2-((1S,2R,3R,5R)-3-ethynyl-2-(3-hydroxypropyl)-3-(benzylamino)-5-methylcyclohexyl)acetonitrile

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

Downstream raw materials:

(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1,1′-dibenzyl-16,16′-dimethyl-11-(trimethylsilyl)-1,1′,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,15′,16,16′,-17,17′-icosahydro-10,10′-bi(5,10bpropano1,7-phenanthroline)

(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-Benzyl-16,16′-dimethyl-10′-(trimethylsilyl)-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,16′,17,17′-octadecahydro[10,11′-bi(5,10b-propano1,7-phenanthroline)]-1′(15′H)-carbaldehyde

C₄₆H₅₄N₄

(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1′-benzyl-16,16′-dimethyl-11-(trimethylsilyl)-1′,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15′,16,16′,17,17′-octadecahydro[10,10′-bi(5,10bpropano-1,7phenanthroline)]-1-(15H)-carbaldehyde

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