(+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene

Base Information

• Chemical Name: (+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene
• CAS No.: 154084-90-9
• Molecular Formula: C₁₁H₁₉I
• Molecular Weight: 278.176
• Mol file: 154084-90-9.mol

Synonyms:(+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene

Chemical Property of (+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene

There total 1 articles about (+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-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: 91.0%

2-(2,6,6-trimethyl-cyclohex-2-enyl)-ethanol (472-63-9) → (+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene (154084-90-9)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)80759-6

Reference yield: 100.0%

1,5-dimethoxy-1,4-cyclohexadiene (37567-78-5) + (+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene (154084-90-9) → 1,5-Dimethoxy-6-[2-(2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-cyclohexa-1,4-diene (154084-91-0)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium; In tetrahydrofuran; pentane; -78 degC, 15 min, allowed to warm to 23 degC, 2 h;

DOI:10.1016/S0040-4020(01)80759-6

Reference yield:

(+/-)-3-(2-Iodoethyl)-2,4,4-trimethyl-1-cyclohexene (154084-90-9) → (1S*,6R*)-1,7,7-Trimethyl-2-oxabicyclo<4.4.0>decan-3-one (52567-91-6,52567-92-7,52567-93-8,60134-41-0,60134-43-2,70051-55-7,78038-67-2,93777-44-7)

Guidance literature:

Multi-step reaction with 6 steps

1: K₂CO₃ / acetone; dimethylformamide / 21 h / 70 °C

2: 88 percent / 70percent m-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 79 percent / aq. LiOH / methanol / 1 h / 55 °C

4: 1.) 80percent m-chloroperoxybenzoic acid, 2.) K₂CO₃ / 1.) CH₂Cl₂, room temp., 95 h, 2.) MeOH, overnight

5: 91 percent / (i-Bu)2AlH / tetrahydrofuran; toluene / 24 h / Ambient temperature

6: 58 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂ / 12 h / Ambient temperature

With lithium hydroxide; dipyridinium dichromate; 3 A molecular sieve; diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

2-(2,6,6-trimethyl-cyclohex-2-enyl)-ethanol

Downstream raw materials:

1,5-Dimethoxy-6-[2-(2,6,6-trimethyl-cyclohex-2-enyl)-ethyl]-cyclohexa-1,4-diene

(+/-)-Ethyl 2-<2-(2,6,6-trimethyl-2-cyclohexen-1-yl)ethyl>-3-oxobutanoate

(1R*,2S*)-2-(3-Hydroxypropyl)-1,3,3-trimethyl-1-cyclohexanol

5-((1R,2S)-2-Hydroxy-2,6,6-trimethyl-cyclohexyl)-3-methylene-pentan-2-one

Refernces

• 1、 Yajima, Arata,Takikawa, Hirosato,Mori, Kenji. "Synthesis of mono- and sesquiterpenoids, XXV: Synthesis of (6R*,7R*)-7-hydroxy-6,11-cyclofarnes-3(15)-en-2-one, the racemate of the antibacterial sesquiterpene from premna oligotricha, and its (6R*,7R*) isomer". . p. 891 - 897. Retrieved 2007/10/03.