Cyclohexanone, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-2-(phenyl seleno)-, (3R,6S)-

Base Information

• Chemical Name: Cyclohexanone, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-2-(phenyl seleno)-, (3R,6S)-
• CAS No.: 673451-17-7
• Molecular Formula: C24H38O2SeSi
• Molecular Weight: 465.61
• Mol file: 673451-17-7.mol

Synonyms:

Chemical Property of Cyclohexanone, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-2-(phenyl seleno)-, (3R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclohexanone, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-2-(phenyl seleno)-, (3R,6S)-

There total 5 articles about Cyclohexanone, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-2-(phenyl seleno)-, (3R,6S)- 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: 64.0%

Phenylselenyl chloride (5707-04-0) + (2S,5R,1'S)-2-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-5-methylcyclohexanone (465532-29-0) → (3R,6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-(phenylseleno)cyclohexanone (673451-17-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/S0040-4039(02)00939-5

Reference yield:

isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2) → (3R,6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-(phenylseleno)cyclohexanone (673451-17-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 48.2 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 0 °C

2.1: Mg; 1,2-dichloroethane / tetrahydrofuran

2.2: 95 percent / copper(I) iodide / tetrahydrofuran / 1.5 h / -30 °C

3.1: 75 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.25 h / 20 °C

4.1: 82 percent / pyridine / 0.5 h / 20 °C

5.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 64 percent / hexamethylphosphorotriamide / tetrahydrofuran; hexane / 1.5 h / -78 °C

With pyridine; tetrapropylammonium perruthennate; 4 A molecular sieve; magnesium; 4-methylmorpholine N-oxide; 1,2-dichloro-ethane; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0040-4020(03)01168-2

Reference yield:

(1R,2R,5R)-5-methyl-2-((S)-2-methyloxiran-2-yl)cyclohexanol (103615-39-0) → (3R,6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-(phenylseleno)cyclohexanone (673451-17-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Mg; 1,2-dichloroethane / tetrahydrofuran

1.2: 95 percent / copper(I) iodide / tetrahydrofuran / 1.5 h / -30 °C

2.1: 75 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.25 h / 20 °C

3.1: 82 percent / pyridine / 0.5 h / 20 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 64 percent / hexamethylphosphorotriamide / tetrahydrofuran; hexane / 1.5 h / -78 °C

With pyridine; tetrapropylammonium perruthennate; 4 A molecular sieve; magnesium; 4-methylmorpholine N-oxide; 1,2-dichloro-ethane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0040-4020(03)01168-2

upstream raw materials:

Phenylselenyl chloride

(2S,5R,1'S)-2-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-5-methylcyclohexanone

isopulegol

(1R,2R,5R)-5-methyl-2-((S)-2-methyloxiran-2-yl)cyclohexanol

Downstream raw materials:

(6S,1'S)-6-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-3-methyl-2-cyclohexenone

(6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-cyclohexenone

Refernces

• 1、 Kim, Jung Hun,Lim, Hyun Jin,Cheon, Seung Hoon. "Synthesis of (+)-hernandulcin and (+)-epihernandulcin". . p. 4721 - 4722. Retrieved 2007/10/03.