(4R)-1,4-dimethyl-4-[(1R)-1-methyl-2-methylidenecyclopentyl]cyclohexene

Base Information

• Chemical Name: (4R)-1,4-dimethyl-4-[(1R)-1-methyl-2-methylidenecyclopentyl]cyclohexene
• CAS No.: 61505-17-7
• Molecular Formula: C15H24
• Molecular Weight: 204.3511
• Mol file: 61505-17-7.mol

Synonyms:Cyclohexene,1,4-dimethyl-4-(1-methyl-2-methylenecyclopentyl)-, (R*,R*)-(?à)-; (?à)-Trichodiene; Cyclohexene,1,4-dimethyl-4-(1-methyl-2-methylenecyclopentyl)-, (R*,R*)-

Chemical Property of (4R)-1,4-dimethyl-4-[(1R)-1-methyl-2-methylidenecyclopentyl]cyclohexene

Chemical Property:

• Vapor Pressure: 0.0244mmHg at 25°C
• Boiling Point: 256.7°Cat760mmHg
• Flash Point: 99.2°C
• Density: 0.89g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4R)-1,4-dimethyl-4-[(1R)-1-methyl-2-methylidenecyclopentyl]cyclohexene

There total 92 articles about (4R)-1,4-dimethyl-4-[(1R)-1-methyl-2-methylidenecyclopentyl]cyclohexene 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: 90.0%

(1S,2R,5R)-2,5-Dimethyl-5-((R)-1-methyl-2-methylene-cyclopentyl)-cyclohexanol → (+/-)-trichodiene (61505-17-7)

Guidance literature:

With trichlorophosphate; In pyridine;

DOI:10.1016/S0040-4039(98)01140-X

Reference yield: 76.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 5-methyl-5-(1-methyl-2-methylenecyclopentyl)oct-7-en-2-one → (+/-)-trichodiene (61505-17-7)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

5-methyl-5-(1-methyl-2-methylenecyclopentyl)oct-7-en-2-one; In tetrahydrofuran; at -78 - 0 ℃; for 1h; Inert atmosphere;

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1039/d1ob01778k

Reference yield: 73.0%

1-methyl-1-(1-methyl-2-methylenecyclopentyl)-4-methylene-2-cyclohexene (116425-56-0) → (+/-)-trichodiene (61505-17-7) + (R)-3,6-Dimethyl-3-((R)-1-methyl-2-methylene-cyclopentyl)-cyclohexene (116425-57-1)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 0.75h; Yields of byproduct given;

DOI:10.1021/jo00280a039

upstream raw materials:

C₁₇H₃₁NO

(2RS,1'SR)-2-(1',4'-dimethylcyclohex-3'-enyl)-2-methylcyclopentan-1-one

1-methyl-1-(1-methyl-2-methylenecyclopentyl)-4-methylene-2-cyclohexene

1-(hydroxymethyl)-4-methyl-1-(1-methyl-2-methylenecyclopentyl)-3-cyclohexene

Refernces

• 1、 Gebauer, Julian,Koch, Matthias,Sebald, Michael A.. "Diastereoselective synthesis of (±)-trichodiene and (±)-trichodiene-D3as analytical standards for the on-site quantification of trichothecenes". . p. 9872 - 9879. Retrieved 2021/12/07.
• 2、 Pearson,O'Brien. "Trichothecine synthesis using organoiron complexes: Diastereoselective total syntheses of (±)-trichodiene, (±)-12,13-epoxytrichothec-9-ene, and (±)-trichodermol". . p. 4663 - 4673. Retrieved 2007/10/02.