1(4H)-Naphthalenone,4a,5,6,7-tetrahydro-4-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4R,4aR,5R)-

Base Information

• Chemical Name: 1(4H)-Naphthalenone,4a,5,6,7-tetrahydro-4-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4R,4aR,5R)-
• CAS No.: 115356-18-8
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• Mol file: 115356-18-8.mol

Synonyms:1(4H)-Naphthalenone,4a,5,6,7-tetrahydro-4-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, [4R-(4a,4ab,5b)]-; (-)-Kanshone A; Kanshone A

Chemical Property of 1(4H)-Naphthalenone,4a,5,6,7-tetrahydro-4-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4R,4aR,5R)-

Chemical Property:

Purity/Quality:

98.0% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1(4H)-Naphthalenone,4a,5,6,7-tetrahydro-4-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4R,4aR,5R)-

There total 35 articles about 1(4H)-Naphthalenone,4a,5,6,7-tetrahydro-4-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4R,4aR,5R)- 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: 60.0%

(2RS,4aR,5R)-4-(1-Hydroxy-1-methylethyl)-4a,5-dimethyl-2-(phenylseleno)-3,4,4a,5,6,7-hexahydronaphthalen-1(2H)-one → kanshone A (115356-18-8)

Guidance literature:

With pyridine; dihydrogen peroxide; In tetrahydrofuran; for 0.666667h; Ambient temperature;

DOI:10.1021/jo00071a025

Reference yield:

(1R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one (128261-64-3) → kanshone A (115356-18-8)

Guidance literature:

Multi-step reaction with 18 steps

1: 76 percent / CuI / tetrahydrofuran / 1 h / -50 - -40 °C

2: m-CPBA / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

3: MsOH, Ac₂O / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 15 h

4: 80 percent / m-CPBA / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

5: 20 percent / K₂CO₃ / acetonitrile / 5 h / 50 °C

6: 20 percent / hydroquinone / xylene / 5 h / Heating

7: 90 percent / CuI / diethyl ether; tetrahydrofuran / 1 h

8: 89 percent / 6percent Na(Hg) / methanol / 1.5 h / -50 - -20 °C

9: 1.) diborane, 2.) 30percent aq. H₂O₂, 3 M aq. NaOH / 1.) THF, 0 deg C, 5 h; r.t., 15 h, 2.) 0 deg C, 4 h; r.t., 20 h

10: 92 percent / (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

11: 50 percent / t-BuOK / CH₂Cl₂ / 0.17 h / Ambient temperature

12: 80 percent / Zn(OAc)2, BF₃*Et₂O / 1.) 0 deg C, 10 min, 2.) r.t., 24 h

13: 95 percent / K₂CO₃ / methanol / 20 h / Ambient temperature

14: 66 percent / m-CPBA / CH₂Cl₂ / 1.) 0 deg C, 5 h, 2.) r.t., 15 h

15: 84 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) reflux, 4 h

16: 98 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

17: 66 percent / LHMDS, HMPA / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 3 h

18: 60 percent / pyridine, 30percent H₂O₂ / tetrahydrofuran / 0.67 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dipyridinium dichromate; sodium amalgam; oxalyl dichloride; methanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; zinc diacetate; dihydrogen peroxide; acetic anhydride; potassium carbonate; dimethyl sulfoxide; hydroquinone; 3-chloro-benzenecarboperoxoic acid; diborane; lithium hexamethyldisilazane; copper(l) iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; xylene;

DOI:10.1021/jo00071a025

Reference yield:

(1R,4R,5R)-4,6,6-Trimethyl-4-<(1R)-1-methyl-3-butenyl>bicyclo<3.1.1>heptan-2-one (139541-68-7) → kanshone A (115356-18-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) diborane, 2.) 30percent aq. H₂O₂, 3 M aq. NaOH / 1.) THF, 0 deg C, 5 h; r.t., 15 h, 2.) 0 deg C, 4 h; r.t., 20 h

2: 92 percent / (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

3: 50 percent / t-BuOK / CH₂Cl₂ / 0.17 h / Ambient temperature

4: 80 percent / Zn(OAc)2, BF₃*Et₂O / 1.) 0 deg C, 10 min, 2.) r.t., 24 h

5: 1.) MeLi, 2.) Et₃N, HMPA / 1.) ether, -78 deg C, 30 min, 2.) -78 to 0 deg C, 3 h

6: Pd(OAc)2 / acetonitrile / 20 h / Ambient temperature

7: 69 percent / m-CPBA / CH₂Cl₂

8: 42 percent / LiBEt₃H

9: 84 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) reflux, 4 h

10: 98 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

11: 66 percent / LHMDS, HMPA / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 3 h

12: 60 percent / pyridine, 30percent H₂O₂ / tetrahydrofuran / 0.67 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; zinc diacetate; methyllithium; dihydrogen peroxide; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; diborane; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo00071a025

upstream raw materials:

(4S,4aS,5S)-4-(1-Hydroxy-1-methyl-ethyl)-4a,5-dimethyl-2-phenylselanyl-3,4,4a,5,6,7-hexahydro-2H-naphthalen-1-one

Methyl (1S*,2R*)-1,2-dimethyl-5-oxocyclohexylacetate Ethylene Acetal

(5R*,6R*,7R*)-5-(1-Hydroxy-1-methylethyl)-6,7-dimethylbicyclo<4.4.0>dec-1(10)-en-2-one

Methyl (1R*,2R*,10R*)-1,10-dimethyl-7-oxobicyclo<4.4.0>dec-5-ene-2-carboxylate