(3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one

Base Information

• Chemical Name: (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one
• CAS No.: 123848-90-8
• Molecular Formula: C₁₈H₂₀O
• Molecular Weight: 252.356
• Mol file: 123848-90-8.mol

Synonyms:

Chemical Property of (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one

There total 9 articles about (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-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: 63.0%

para-methylphenylmagnesium bromide (4294-57-9) + 5-methyl-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one (124018-43-5) → (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one (123848-90-8)

Guidance literature:

With copper(l) iodide; boron trifluoride diethyl etherate; In diethyl ether; from -20 degC to room t.;

DOI:10.1039/c39890000271

Reference yield:

endo-Dicyclopentadien (1755-01-7,25038-78-2) → (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one (123848-90-8)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂O; dioxane / 2 h / Heating

2: 30 percent / lipase / acetone; various solvent(s) / 120 h / Ambient temperature

3: 90 percent / pyridinium chlorochromate / CH₂Cl₂ / 12 h / Ambient temperature

4: 65 percent / tetrahydrofuran / 0.25 h / -70 °C

5: 63 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / from 0 degC to room t.

6: 63 percent / copper(I) iodide, boron trifluoride-ether / diethyl ether / from -20 degC to room t.

With copper(l) iodide; boron trifluoride diethyl etherate; pyridinium chlorochromate; lipase; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetone;

DOI:10.1039/c39890000271

Reference yield:

5-exo-hydroxytricyclo[5.2.1.0(2,6)]deca-3,8-diene (875-20-7,6814-80-8,24529-79-1,24708-29-0,57386-40-0,88555-62-8,105367-92-8,122919-96-4,123930-79-0) → (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one (123848-90-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 30 percent / lipase / acetone; various solvent(s) / 120 h / Ambient temperature

2: 90 percent / pyridinium chlorochromate / CH₂Cl₂ / 12 h / Ambient temperature

3: 65 percent / tetrahydrofuran / 0.25 h / -70 °C

4: 63 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / from 0 degC to room t.

5: 63 percent / copper(I) iodide, boron trifluoride-ether / diethyl ether / from -20 degC to room t.

With copper(l) iodide; boron trifluoride diethyl etherate; pyridinium chlorochromate; lipase; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1039/c39890000271

upstream raw materials:

para-methylphenylmagnesium bromide

5-methyl-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one

(1R,2S,6R,7S)-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one

(3aR)-3aα,4,7,7aα-tetrahydro-4α,7α-methano-1(H)-inden-1α-ol

Downstream raw materials:

(S)-(-)-4-methyl-4-(4-methylphenyl)cyclopent-2-enone

Refernces