methyl cis-4-n-propylcyclohexanecarboxylate

Base Information

• Chemical Name: methyl cis-4-n-propylcyclohexanecarboxylate
• CAS No.: 101691-32-1
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.279
• Mol file: 101691-32-1.mol

Synonyms:methyl cis-4-n-propylcyclohexanecarboxylate

Chemical Property of methyl cis-4-n-propylcyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of methyl cis-4-n-propylcyclohexanecarboxylate

There total 1 articles about methyl cis-4-n-propylcyclohexanecarboxylate 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: 75.0%

p-(methoxycarbonyl)-n-propylbenzene (81631-63-2) → methyl trans-4-n-propylcyclohexanecarboxylate (117169-72-9) + methyl cis-4-n-propylcyclohexanecarboxylate (101691-32-1)

Guidance literature:

With hydrogen; tetra(n-butyl)ammonium hydrogensulfate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In hexane; for 5h; under 38000 Torr; Product distribution; various reagents, and catalysts;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl cis-4-n-propylcyclohexanecarboxylate (101691-32-1) → (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-3-(4-propyl-cyclohexyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (117169-75-2,135559-35-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, hexane, -78 deg C, 2.5 h

2: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

3: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

4: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

5: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

With n-butyllithium; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; acetic acid; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl cis-4-n-propylcyclohexanecarboxylate (101691-32-1) → 9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F2 methyl ester 11,15-bistetrahydropyranyl ether (72519-94-9,101758-82-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, hexane, -78 deg C, 2.5 h

2: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

3: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

4: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

5: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

6: K₂CO₃ / methanol / 1 h / 45 °C

7: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature

With n-butyllithium; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.36.1128

upstream raw materials:

p-(methoxycarbonyl)-n-propylbenzene

Downstream raw materials:

dimethyl 2-oxo-2-cis-(4-n-propylcyclohexyl)ethyl phosphonate

9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether

15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-6,9α-nitriloprostaglandin F₁ methyl ester

9-acetyl-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F_2α methyl ester