(1S,1aβ,7aβ)-Decahydro-1,6β,6aβ-trimethyl-1α,2aα-methano-2aH-cyclopropa[b]naphthalen-3β-ol

Base Information

• Chemical Name: (1S,1aβ,7aβ)-Decahydro-1,6β,6aβ-trimethyl-1α,2aα-methano-2aH-cyclopropa[b]naphthalen-3β-ol
• CAS No.: 28957-57-5
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• Mol file: 28957-57-5.mol

Synonyms:1,2a-Methano-2aH-cyclopropa[b]naphthalen-3-ol,decahydro-1,6,6a-trimethyl-, (1S,1aR,2aS,6R,6aS,7aS)- (8CI);1,2a-Methano-2aH-cyclopropa[b]naphthalen-3-ol, decahydro-1,6,6a-trimethyl-,[1S-(1a,1ab,2aa,3b,6b,6ab,7ab)]-; Ishwarol

Chemical Property of (1S,1aβ,7aβ)-Decahydro-1,6β,6aβ-trimethyl-1α,2aα-methano-2aH-cyclopropa[b]naphthalen-3β-ol

Chemical Property:

• Boiling Point: 110 °C (1 mmHg)
• PSA: 20.23000
• LogP: 3.21970

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,1aβ,7aβ)-Decahydro-1,6β,6aβ-trimethyl-1α,2aα-methano-2aH-cyclopropa[b]naphthalen-3β-ol

There total 15 articles about (1S,1aβ,7aβ)-Decahydro-1,6β,6aβ-trimethyl-1α,2aα-methano-2aH-cyclopropa[b]naphthalen-3β-ol 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: 88.0%

C15H21ClO (66245-31-6) → (+/-)-ishwarol (28957-57-5,66289-30-3,76231-79-3)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; for 20h; Ambient temperature;

Reference yield:

(3R,4R)-3-(4-Hydroxy-but-2-ynyl)-3,4-dimethyl-cyclohexanone (66245-21-4) → (+/-)-ishwarol (28957-57-5,66289-30-3,76231-79-3)

Guidance literature:

Multi-step reaction with 11 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

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

Reference yield:

4-((7S,8S)-7,8-Dimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-but-2-yn-1-ol (66245-20-3) → (+/-)-ishwarol (28957-57-5,66289-30-3,76231-79-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 92 percent / 3 N hydrochloric acid, water / methanol / 3 h / Ambient temperature

2: 95 percent / hydrogen, quinoline / 5percent palladium on barium sulfate / ethanol / Ambient temperature

3: 96 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

4: 1.56 g / potassium tert-butoxide / 2-methyl-propan-2-ol / 2.5 h / Ambient temperature

5: 85 percent / p-toluenesulfonic acid / benzene / 20 h / Heating

6: 64 percent / copper bronze / 1.5 h / 130 - 140 °C

7: 94 percent / lithium aluminum hydride / diethyl ether / 20 h / Ambient temperature

8: 84 percent / water, 4 N hydrochloric acid / acetone / 3 h / Ambient temperature

9: 370 mg / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

10: 242 mg / lithium chloride, hexamethylphosphoramide / diethyl ether

11: 141 mg / potassium tert-butoxide / tetrahydrofuran / 1.5 h / Ambient temperature

12: 88 percent / lithium triethylborohydride / tetrahydrofuran / 20 h / Ambient temperature

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

upstream raw materials:

Ishwaron

C₁₅H₂₁ClO

(4S,4aR,8aS)-4,4a-Dimethyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one

(3R,4R)-3-((Z)-4-Hydroxy-but-2-enyl)-3,4-dimethyl-cyclohexanone

Downstream raw materials:

(+/-)-ishwarane

(+/-)-ishwarone