3-Cyclohexene-1-carboxylicacid,1,6-dimethyl-,(1R,6R)-(9CI)

Base Information

• Chemical Name: 3-Cyclohexene-1-carboxylicacid,1,6-dimethyl-,(1R,6R)-(9CI)
• CAS No.: 421555-39-7
• Molecular Formula: C9H14O2
• Molecular Weight: 154.20600
• Mol file: 421555-39-7.mol

Synonyms:3-Cyclohexene-1-carboxylic acid,1,6-dimethyl-,(1R,6R);

Chemical Property of 3-Cyclohexene-1-carboxylicacid,1,6-dimethyl-,(1R,6R)-(9CI)

Chemical Property:

• PSA: 37.30000
• LogP: 2.06340

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Cyclohexene-1-carboxylicacid,1,6-dimethyl-,(1R,6R)-(9CI)

There total 2 articles about 3-Cyclohexene-1-carboxylicacid,1,6-dimethyl-,(1R,6R)-(9CI) 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:

1,6-dimethyl-cyclohex-3-enecarbaldehyde (877659-54-6) → cis-1,2-Dimethyl-cyclohex-3-en-carbonsaeure (421555-39-7)

Guidance literature:

With jones' reagent; In acetone; at 0 ℃; for 1h;

DOI:10.1021/ja057483x

Reference yield:

2-methylbut-2-enal (497-03-0) → cis-1,2-Dimethyl-cyclohex-3-en-carbonsaeure (421555-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (R)-3,3-Ph₂-1-o-Tol-pyrrolidino[1,2c][1,3,2]oxazaborole*Tf₂N / CH₂Cl₂ / 21 h / 20 °C

2: Jones' reagent / acetone / 1 h / 0 °C

With (R)-(+)-3,3-diphenyl-1-o-tolyl-tetrahydropyrrolo-(1,2-c)(1,3,2)oxazaborole-1,1,1-trifluoro-N-((trifluoromethyl)-sulfonyl)methanesulfonamide; jones' reagent; In dichloromethane; acetone; 1: Diels-Alder reaction;

DOI:10.1021/ja057483x

Reference yield:

cis-1,2-Dimethyl-cyclohex-3-en-carbonsaeure (421555-39-7) → (1R,2R,3S)-3-tert-Butyl-1,2-dimethyl-cyclohexanecarbaldehyde (877659-71-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aq. NaHCO₃; KI; I₂ / tetrahydrofuran / 6 h / 0 °C

2.1: DBU / tetrahydrofuran / 12 h / Heating

3.1: methanol / 3 h / 20 °C

4.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

5.1: CuCN / tetrahydrofuran; pentane / 1 h / -78 °C

5.2: Me₃SiCl / pentane; tetrahydrofuran / 2 h / -78 °C

6.1: tosyl hydrazide; p-TsOH; NaBH₃CN / dimethylformamide; tetrahydrothiophene 1,1-dioxide / 2 h / 100 °C

7.1: diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

8.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

With iodine; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; pyridinium chlorochromate; potassium iodide; In tetrahydrofuran; sulfolane; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ja057483x

upstream raw materials:

1,6-dimethyl-cyclohex-3-enecarbaldehyde

2-methylbut-2-enal

Downstream raw materials:

1,2-dimethyl-5-oxo-cyclohex-3-enecarboxylic acid methyl ester

(1R,2R,5S)-5-Hydroxy-1,2-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

(1R,2R,3S)-3-tert-Butyl-1,2-dimethyl-cyclohexanecarbaldehyde

3-tert-butyl-1,2-dimethyl-cyclohexanecarboxylic acid methyl ester