(+/-)-ishwarone

Base Information

• Chemical Name: (+/-)-ishwarone
• CAS No.: 29126-71-4
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• Mol file: 29126-71-4.mol

Synonyms:

Chemical Property of (+/-)-ishwarone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-ishwarone

There total 21 articles about (+/-)-ishwarone 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: 73.0%

(+/-)-ishwarol (28957-57-5,66289-30-3,76231-79-3) → (+/-)-ishwarone (22471-56-3,29126-71-4)

Guidance literature:

With chromium(VI) oxide; pyridine hydrochloride; In dichloromethane; for 2h; Ambient temperature;

Reference yield: 2.0%

(2aS,3R,6aS)-1,1-Dibromo-2a,3,6a,7a-tetramethyl-decahydro-cyclopropa[b]naphthalen-6-one (73723-57-6,93602-39-2) → racemic ishwarone (22471-56-3,29126-71-4)

Guidance literature:

With methyllithium; In diethyl ether; Ambient temperature;

DOI:10.1139/v84-328

Reference yield:

(3R,4R)-3-(4-Hydroxy-but-2-ynyl)-3,4-dimethyl-cyclohexanone (66245-21-4) → (+/-)-ishwarone (22471-56-3,29126-71-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / hydrogen, quinoline / 5percent palladium on barium sulfate / ethanol / Ambient temperature

2: 96 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.56 g / potassium tert-butoxide / 2-methyl-propan-2-ol / 2.5 h / Ambient temperature

4: 85 percent / p-toluenesulfonic acid / benzene / 20 h / Heating

5: 64 percent / copper bronze / 1.5 h / 130 - 140 °C

6: 94 percent / lithium aluminum hydride / diethyl ether / 20 h / Ambient temperature

7: 84 percent / water, 4 N hydrochloric acid / acetone / 3 h / Ambient temperature

8: 370 mg / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

9: 242 mg / lithium chloride, hexamethylphosphoramide / diethyl ether

10: 141 mg / potassium tert-butoxide / tetrahydrofuran / 1.5 h / Ambient temperature

11: 88 percent / lithium triethylborohydride / tetrahydrofuran / 20 h / Ambient temperature

12: 73 percent / chromium trioxide, pyridinium hydrochloride / CH₂Cl₂ / 2 h / Ambient temperature

With quinoline; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; potassium tert-butylate; water; hydrogen; pyridine hydrochloride; copper; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; lithium chloride; Pd-BaSO₄; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone; tert-butyl alcohol; benzene;

upstream raw materials:

(2aS,3R,6aS)-1,1-Dibromo-2a,3,6a,7a-tetramethyl-decahydro-cyclopropa[b]naphthalen-6-one

2,3,4-trimethyltricyclohex-2-en-1-one

4-iodo-2-methyl-but-1-ene

3-isobutoxy-2,6-dimethylcyclohex-2-en-1-one

Downstream raw materials:

ishwarane

Ishwarol

(1R,2S,4S,5R,9R,11R)-3-ishwarone

(+/-)-ishwarane