(2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate

Base Information

• Chemical Name: (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate
• CAS No.: 13835-32-0
• Molecular Formula: C₁₇H₂₀N₂O₆
• Molecular Weight: 348.356
• Mol file: 13835-32-0.mol

Synonyms:(2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate

Chemical Property of (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate

There total 11 articles about (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate 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: 16.0%

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol (287720-47-2) + 3,5-dinitrobenoyl chloride (99-33-2) → (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate (13835-32-0)

Guidance literature:

With pyridine; for 4h;

DOI:10.1055/s-0036-1588645

Reference yield:

(2R,5R)-5-isopropenyl-2-methylcyclohexanone (5524-05-0) → (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate (13835-32-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / paraffin oil; tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Reflux

3.1: manganese(IV) oxide / dichloromethane / 64 h / 20 °C

4.1: 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / chloroform / 18 h / -30 °C

5.1: n-butyllithium / diethyl ether; hexane / 0.5 h / 0 - 20 °C

5.2: 16 h / 0 - 20 °C

6.1: chromium(VI) oxide; tert.-butylhydroperoxide / dichloromethane / 2 h

7.1: methanol / 18 h / 20 °C / Irradiation; Inert atmosphere

8.1: diethyl ether / 3 h / 0 - 20 °C

9.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C

10.1: pyridine / 4 h

With pyridine; chromium(VI) oxide; tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; dihydrogen peroxide; sodium hydride; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; paraffin oil; 1.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1055/s-0036-1588645

Reference yield:

ethyl (E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]acetate (141277-82-9) → (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl 3,5-dinitrobenzoate (13835-32-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Reflux

2.1: manganese(IV) oxide / dichloromethane / 64 h / 20 °C

3.1: 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / chloroform / 18 h / -30 °C

4.1: n-butyllithium / diethyl ether; hexane / 0.5 h / 0 - 20 °C

4.2: 16 h / 0 - 20 °C

5.1: chromium(VI) oxide; tert.-butylhydroperoxide / dichloromethane / 2 h

6.1: methanol / 18 h / 20 °C / Irradiation; Inert atmosphere

7.1: diethyl ether / 3 h / 0 - 20 °C

8.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C

9.1: pyridine / 4 h

With pyridine; chromium(VI) oxide; tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water;

DOI:10.1055/s-0036-1588645

upstream raw materials:

menth-1-en-9-ol

3,5-dinitrobenoyl chloride

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol

(2R,5R)-5-isopropenyl-2-methylcyclohexanone

Downstream raw materials:

(2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-1-ol

(S)-2-Methyl-6-((R)-4-methyl-cyclohex-3-enyl)-heptan-4-one

(R)-4-((S)-1,5-Dimethyl-3-oxo-hexyl)-cyclohex-1-enecarbaldehyde

(+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester