(4αR,5R)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

Base Information

• Chemical Name: (4αR,5R)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one
• CAS No.: 34996-06-0
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.247
• Mol file: 34996-06-0.mol

Synonyms:(4αR,5R)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

Chemical Property of (4αR,5R)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4αR,5R)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

There total 18 articles about (4αR,5R)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-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: 100.0%

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione (33878-99-8) → (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one (878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 0.25h; chemoselective reaction;

DOI:10.1021/acs.joc.6b02264

Reference yield: 50.0%

Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) → (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one (878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9) + (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one (257941-62-1)

Guidance literature:

With glucose dehydrogenase; 7α-hydroxysteroid dehydrogenase from extremophilic bacterium Deinococcus marmoris strain; NADPH; In aq. phosphate buffer; dimethyl sulfoxide; at 25 ℃; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/ejoc.202100174

Reference yield: 50.0%

vinyl acetate (108-05-4,9003-20-7) + (±)-4a,5-cis-(5-hydroxy-4a-methyl-4,4 a,5,6,7,8-hexahydronaphthalen-2(3H)-one) (4242-00-6) → (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one (878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9) + (-)-1β-acetoxy-1,2,3,4,8,8a-hexahydro-8aβ-methyl-6(7H)-naphthalenone (148683-74-3)

Guidance literature:

With Amano Lipase PS; In acetone; at 45 ℃; for 144h; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/ejoc.202100174

upstream raw materials:

Wieland-Miescher ketone

(±)-4a,5-cis-(5-hydroxy-4a-methyl-4,4 a,5,6,7,8-hexahydronaphthalen-2(3H)-one)

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

[(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Downstream raw materials:

(4aS,5S)-5-tert-Butoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

(+)-(4aS,5S)-5-benzoyloxy-4,4a,5,6,7,8-hexahydro-4a-methylnaphthalen-2(3H)-one

1β-tert-butoxy-8aβ-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-6-one

(4aS,5R)-5-(t-Butoxy)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalin-2-on