Cyclohexene, 1-(bromomethyl)-4-(1-methylethenyl)-, (S)-

Base Information

• Chemical Name: Cyclohexene, 1-(bromomethyl)-4-(1-methylethenyl)-, (S)-
• CAS No.: 83059-12-5
• Molecular Formula: C10H15Br
• Molecular Weight: 215.133
• DSSTox Substance ID: DTXSID70454293
• Nikkaji Number: J3.289.877G
• Wikidata: Q82275731
• Mol file: 83059-12-5.mol

Synonyms:83059-12-5;(?)-Perillyl bromide;Cyclohexene, 1-(bromomethyl)-4-(1-methylethenyl)-, (S)-;DTXSID70454293

Chemical Property of Cyclohexene, 1-(bromomethyl)-4-(1-methylethenyl)-, (S)-

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 214.03571
• Heavy Atom Count: 11
• Complexity: 179

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC(=CC1)CBr
• Isomeric SMILES: CC(=C)[C@H]1CCC(=CC1)CBr

Technology Process of Cyclohexene, 1-(bromomethyl)-4-(1-methylethenyl)-, (S)-

There total 2 articles about Cyclohexene, 1-(bromomethyl)-4-(1-methylethenyl)-, (S)- 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%

(-)-perillyl alcohol (536-59-4,18457-55-1) → (S)-1-(bromomethyl)-4-(prop-1-en-2-yl)cyclohex-1-ene (83059-12-5)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In benzene; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00407

Reference yield:

(S)-(-)-perillaldehyde (18031-40-8) → (S)-1-(bromomethyl)-4-(prop-1-en-2-yl)cyclohex-1-ene (83059-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / NaBH₄ / ethanol; diethyl ether / 1 h / Ambient temperature

2: 2.55 g / PBr₃ / diethyl ether / 5 h / Ambient temperature

With sodium tetrahydroborate; phosphorus tribromide; In diethyl ether; ethanol;

DOI:10.1002/hlca.19820650323

Reference yield: 90.0%

methyl 4-formylbutanoate (6026-86-4) + (S)-1-(bromomethyl)-4-(prop-1-en-2-yl)cyclohex-1-ene (83059-12-5) → C16H26O3

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; for 3h;

DOI:10.1021/acs.orglett.8b00407

upstream raw materials:

(-)-perillyl alcohol

(S)-(-)-perillaldehyde

Downstream raw materials:

ethyl 2-[(4-isopropenyl-1-cyclohexenyl)methyl]-3-(1-methylcyclopropyl)-3-oxopropanoate

(E)-1-iodo-6-(4-isopropenyl-1-cyclohexenyl)-3-methyl-3-hexene

3-[(E)-6-(4-isopropenyl-1-cyclohexenyl)-3-methyl-3-hexenyl]-2-cyclohexen-1-one

3-[(E)-6-(4-isopropenyl-1-cyclohexenyl)-3-methyl-3-hexenyl]-3-methyl-1-cyclohexenyl trimethylsilyl ether