(+/-)-kempene-2

Base Information

• Chemical Name: (+/-)-kempene-2
• CAS No.: 135096-60-5
• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.478
• Mol file: 135096-60-5.mol

Synonyms:

Chemical Property of (+/-)-kempene-2

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-kempene-2

There total 22 articles about (+/-)-kempene-2 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: 32.0%

Acetic acid (3aR,5aS,6R,8R,9S,9aS,9bR)-1-acetyl-3a,8,9a-trimethyl-4-oxo-9-(2-oxo-ethyl)-3a,4,5,5a,6,7,8,9,9a,9b-decahydro-3H-cyclopenta[a]naphthalen-6-yl ester (135041-61-1) → (+/-)-kempene-2 (65118-74-3,135096-60-5)

Guidance literature:

With TiCl₃-1,2-dimethoxyethane; copper; zinc; In 1,2-dimethoxyethane; for 2h; Heating;

DOI:10.1021/ja00015a064

Reference yield:

2,6-dimethyl-1,4-benzoquinone (527-61-7) → (+/-)-kempene-2 (65118-74-3,135096-60-5)

Guidance literature:

Multi-step reaction with 21 steps

1: 1.) BF₃*Et₂O, 2.) Zn, HOAc / 1.) 96 h, 2.) reflux, 18 h

2: 1.) L-Selectride, 2.) NaOH, H₂O₂ / 1.) THF, -78 deg C, 2.) THF, 0 deg C

3: 83 percent / NaH, Bu₄NI / tetrahydrofuran / 72 h

4: 1.) sec-BuLi / 1.) THF, from -60 deg C to -20 deg C, 1 h, 2.) THF, -40 deg C, 30 min

5: ethanol

6: 1.) KOtBu / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 18 h

7: disiamylborane / tetrahydrofuran / 72 h / 40 °C

8: H₂O₂, NaOH / 0 °C

9: 98 percent / NaH, Bu₄NI / tetrahydrofuran / 48 h

10: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) 0 deg C, 6 h

11: 90 percent / (COCl)2, DMSO / CH₂Cl₂

12: 1.) pyridinium bromide perbromide, 2.) LiBr, Li₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) DMF, 120 deg C, 16 h

13: 66 percent / EtAlCl₂ / toluene / 24 h / 80 °C

14: 95 percent / (CH₃)3NO / OsO₄ / acetone; H₂O

15: 88 percent / H₂ / 10percent Pd/C / ethyl acetate

16: 81 percent / NaIO₄ / dioxane; H₂O

17: 61 percent / TsOH*H₂O / benzene / 2 h / 80 °C

18: 66 percent / pyridine, DMAP

19: 68 percent / HCl / ethanol / 2 h / 80 °C

20: 57 percent / PCC/Al₂O₃ / hexane; CH₂Cl₂

21: 32 percent / TiCl₃*1.5DME, Zn-Cu / 1,2-dimethoxy-ethane / 2 h / Heating

With pyridine; hydrogenchloride; dmap; aluminum oxide; sodium hydroxide; sodium periodate; borane-THF; oxalyl dichloride; TiCl₃-1,2-dimethoxyethane; trimethylamine-N-oxide; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; dihydrogen peroxide; sec.-butyllithium; pyridinium hydrobromide perbromide; ethylaluminum dichloride; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; lithium carbonate; L-Selectride; copper; sodium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; pyridinium chlorochromate; lithium bromide; zinc; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; benzene;

DOI:10.1021/ja00015a064

Reference yield:

(2R,4R,4aS,8aS)-4-Hydroxy-2,7,8a-trimethyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one (105018-93-7) → (+/-)-kempene-2 (65118-74-3,135096-60-5)

Guidance literature:

Multi-step reaction with 19 steps

1: 83 percent / NaH, Bu₄NI / tetrahydrofuran / 72 h

2: 1.) sec-BuLi / 1.) THF, from -60 deg C to -20 deg C, 1 h, 2.) THF, -40 deg C, 30 min

3: ethanol

4: 1.) KOtBu / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 18 h

5: disiamylborane / tetrahydrofuran / 72 h / 40 °C

6: H₂O₂, NaOH / 0 °C

7: 98 percent / NaH, Bu₄NI / tetrahydrofuran / 48 h

8: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) 0 deg C, 6 h

9: 90 percent / (COCl)2, DMSO / CH₂Cl₂

10: 1.) pyridinium bromide perbromide, 2.) LiBr, Li₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) DMF, 120 deg C, 16 h

11: 66 percent / EtAlCl₂ / toluene / 24 h / 80 °C

12: 95 percent / (CH₃)3NO / OsO₄ / acetone; H₂O

13: 88 percent / H₂ / 10percent Pd/C / ethyl acetate

14: 81 percent / NaIO₄ / dioxane; H₂O

15: 61 percent / TsOH*H₂O / benzene / 2 h / 80 °C

16: 66 percent / pyridine, DMAP

17: 68 percent / HCl / ethanol / 2 h / 80 °C

18: 57 percent / PCC/Al₂O₃ / hexane; CH₂Cl₂

19: 32 percent / TiCl₃*1.5DME, Zn-Cu / 1,2-dimethoxy-ethane / 2 h / Heating

With pyridine; hydrogenchloride; dmap; aluminum oxide; sodium hydroxide; sodium periodate; borane-THF; oxalyl dichloride; TiCl₃-1,2-dimethoxyethane; trimethylamine-N-oxide; potassium tert-butylate; hydrogen; dihydrogen peroxide; sec.-butyllithium; pyridinium hydrobromide perbromide; ethylaluminum dichloride; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; lithium carbonate; copper; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; pyridinium chlorochromate; lithium bromide; zinc; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; benzene;

DOI:10.1021/ja00015a064

upstream raw materials:

Acetic acid (3aR,5aS,6R,8R,9S,9aS,9bR)-1-acetyl-3a,8,9a-trimethyl-4-oxo-9-(2-oxo-ethyl)-3a,4,5,5a,6,7,8,9,9a,9b-decahydro-3H-cyclopenta[a]naphthalen-6-yl ester

2,6-dimethyl-1,4-benzoquinone

(2R,4R,4aS,8aS)-4-Hydroxy-2,7,8a-trimethyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one

(2R,4aS,8aS)-2,7,8a-Trimethyl-2,3,4a,5,8,8a-hexahydro-[1,4]naphthoquinone