cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.0^2,6>undecan-11-one

Base Information

• Chemical Name: cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.0^2,6>undecan-11-one
• CAS No.: 84607-53-4
• Molecular Formula: C₂₀H₂₆OSe
• Molecular Weight: 361.386
• Mol file: 84607-53-4.mol

Synonyms:cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.0^2,6>undecan-11-one

Chemical Property of cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.0^2,6>undecan-11-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.0^2,6>undecan-11-one

There total 10 articles about cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.0^2,6>undecan-11-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: 62.0%

N-phenylselanylphthalimide (71098-88-9) + cis-anti-cis-4,4-dimethyl-1β-hydroxymethyltricyclo<6.3.0.02,6>undecan-11-one (84607-52-3) → cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.02,6>undecan-11-one (84607-53-4)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96715-8

Reference yield:

2-carbomethoxy-3-(4',4'-dimethylcyclopent-2-enylmethyl)cyclopentanone (84607-50-1) → cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.02,6>undecan-11-one (84607-53-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / SnCl₄ / CH₂Cl₂ / 2.5 h / Ambient temperature

2: Raney-nickel / ethanol / 0.33 h / 50 °C

3: LiNHiPr₂, LiAlH₄ / tetrahydrofuran / 1.3 h / -45 deg C to r.t.

4: 62 percent / n-Bu₃P

With lithium aluminium tetrahydride; tributylphosphine; tin(IV) chloride; nickel; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1039/c39820001252

Reference yield:

methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) → cis-anti-cis-4,4-dimethyl-1β-phenylselenomethyltricyclo<6.3.0.02,6>undecan-11-one (84607-53-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / Mg, CuBr, Me₂S / -30 - 0 °C

2: 45 percent / SnCl₄ / CH₂Cl₂ / 2.5 h / Ambient temperature

3: Raney-nickel / ethanol / 0.33 h / 50 °C

4: LiNHiPr₂, LiAlH₄ / tetrahydrofuran / 1.3 h / -45 deg C to r.t.

5: 62 percent / n-Bu₃P

With lithium aluminium tetrahydride; dimethylsulfide; tributylphosphine; tin(IV) chloride; nickel; magnesium; copper(I) bromide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1039/c39820001252

upstream raw materials:

N-phenylselanylphthalimide

cis-anti-cis-4,4-dimethyl-1β-hydroxymethyltricyclo<6.3.0.0^2,6>undecan-11-one

4,4-dimethylcyclopent-2-enylmethyl bromide

cis-anti-cis-1β-carbomethoxy-4,4-dimethyltricyclo<6.3.0.0^2,6>undecan-11-one