1,5-dimethyl-1,5-cyclooctadiene

Base Information

• Chemical Name: 1,5-dimethyl-1,5-cyclooctadiene
• CAS No.: 73022-52-3
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.237
• Mol file: 73022-52-3.mol

Synonyms:1,5-dimethyl-1,5-cyclooctadiene

Chemical Property of 1,5-dimethyl-1,5-cyclooctadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,5-dimethyl-1,5-cyclooctadiene

There total 12 articles about 1,5-dimethyl-1,5-cyclooctadiene 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%

1,5-dibromo-1,5-cyclooctadiene (158834-31-2) → 1,5-dimethyl-1,5-cyclooctadiene (73022-52-3,3760-14-3)

Guidance literature:

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; at 0 ℃; for 3.5h; Inert atmosphere; Reflux;

DOI:10.3987/COM-08-S(F)102

Reference yield:

isoprene (78-79-5,9003-31-0) → 1-methyl-5-(1-methylethenyl)cyclohexene (13898-73-2) + 1,4-dimethyl-4-vinylcyclohex-1-ene (1743-61-9) + 1,5-dimethyl-1,5-cyclooctadiene (73022-52-3) + 1,6-dimethyl-1,5-cyclo-octadiene (115929-14-1)

Guidance literature:

bis(acetylacetonate)nickel(II); tris(hexafluoroisopropyl) phosphite; triethylaluminum; In tetrahydrofuran; 2,2,4-trimethylpentane; for 0.7h; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)97949-9

Reference yield:

isoprene (78-79-5,9003-31-0) → 1,4-dimethyl-4-vinylcyclohex-1-ene (1743-61-9) + 1,5-dimethyl-1,5-cyclooctadiene (73022-52-3) + 2,4-dimethyl-4-vinylcyclohexene (1611-21-8) + 1,6-dimethyl-1,5-cyclo-octadiene (115929-14-1) + (E)-2,7-dimethyl-1,3,6-octatriene (23012-86-4) + limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; (D)EPHOSNH; at 40 ℃; for 19h; Product distribution;

DOI:10.1021/ja00159a086

upstream raw materials:

7-methyl-3-methene-1,6-octadiene

isoprene

1,2-dimethylenecyclobutane

1,5-dibromo-1,5-cyclooctadiene

Downstream raw materials:

1-Phenyl-2-phenylamino-2-heptene-1,4-dione

8-acetoxy-1,5-dimethylbicyclo<3.2.1>octane

(Z)-(3S,3aS,9aS)-6,9a-Dimethyl-2-phenyl-2,3,3a,4,5,8,9,9a-octahydro-cycloocta[d]isoxazole-3-carboxylic acid phenylamide

1,5-Dimethylcyclooctan

Refernces

• 1、 Kennedy, C. Rose,Zhong, Hongyu,MacAulay, Rachel L.,Chirik, Paul J.. "Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes". supporting information. p. 8557 - 8573. Retrieved 2019/06/04.
• 2、 Wakabayashi, Kazuki,Aikawa, Kohsuke,Mikami, Koichi. "Chirality control of tropos diphenylmethane-derived phosphoramidites by chiral dienes: Its application to asymmetric Michael addition". experimental part. p. 927 - 943. Retrieved 2010/10/20.