(E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester
• CAS No.: 179915-19-6
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• Mol file: 179915-19-6.mol

Synonyms:(E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester

Chemical Property of (E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester

There total 1 articles about (E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester 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:

[2-Methyl-cyclohex-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine (193468-09-6) + propynoic acid methyl ester (922-67-8) → (E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester (179915-19-6) + (E)-3-((S)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester

Guidance literature:

With acetic acid; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) room temperature, 4 d, 2.) water, 60 deg C, 1 h;

DOI:10.1021/jo952253u

Reference yield:

(E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester (179915-19-6) → (R)-2-Methyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone (179749-19-0)

Guidance literature:

Multi-step reaction with 5 steps

1: TsOH / benzene / Heating

2: LiAlH₄ / diethyl ether / 3 h

3: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 10 min

4: 1.) nBuLi / 1.) ether, room temperature, 1 h, 2.) ether, 50 min

5: TsOH / acetone; H₂O / 50 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In diethyl ether; water; acetone; benzene;

DOI:10.1021/jo952253u

Reference yield:

(E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester (179915-19-6) → 2-[(R)-2,6-Dimethyl-6-((E)-4-methyl-penta-1,3-dienyl)-cyclohex-1-enylmethyl]-benzene-1,4-diol (179749-28-1)

Guidance literature:

Multi-step reaction with 9 steps

1: TsOH / benzene / Heating

2: LiAlH₄ / diethyl ether / 3 h

3: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 10 min

4: 1.) nBuLi / 1.) ether, room temperature, 1 h, 2.) ether, 50 min

5: TsOH / acetone; H₂O / 50 °C

6: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, 9 h

7: 1.) magnesium, iodine / 1.) THF, room temperature, 30 min, 2.) THF, 20 min

8: thionyl chloride, pyridine / 0.5 h / 0 °C

9: HCl / tetrahydrofuran / 3.5 h / 50 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; iodine; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; water; acetone; benzene;

DOI:10.1021/jo952253u

upstream raw materials:

[2-Methyl-cyclohex-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine

propynoic acid methyl ester

Downstream raw materials:

(R)-(+)-2-(2'-carbomethoxyethyl)-2-methylcyclohexanone

(R)-2-Methyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone

2-[(R)-2,6-Dimethyl-6-((E)-4-methyl-penta-1,3-dienyl)-cyclohex-1-enylmethyl]-benzene-1,4-diol

2-[(R)-2,6-Dimethyl-6-((E)-4-methyl-penta-1,3-dienyl)-cyclohex-1-enylmethyl]-4-methoxy-1-methoxymethoxy-benzene