Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester

Base Information

• Chemical Name: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester
• CAS No.: 25402-06-6
• Molecular Formula: C20H28 O3
• Molecular Weight: 316.441
• DSSTox Substance ID: DTXSID901018992
• Mol file: 25402-06-6.mol

Synonyms:4.Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester;CINERIN I;97-12-1;DTXSID901018992;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester

Chemical Property of Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester

Chemical Property:

• Vapor Pressure: 1.02E-06mmHg at 25°C
• Refractive Index: nD20 1.5064
• Boiling Point: 403.5°Cat760mmHg
• Flash Point: 173°C
• PSA: 43.37000
• Density: 1.04g/cm³
• LogP: 4.39210
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 600

Purity/Quality:

99% ^*data from raw suppliers

CinerinI ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Pyrethrins/Pyrethroids
• Canonical SMILES: CC=CCC1=C(C(CC1=O)OC(=O)C2C(C2(C)C)C=C(C)C)C
• Isomeric SMILES: C/C=C/CC1=C([C@H](CC1=O)OC(=O)C2[C@H](C2(C)C)C=C(C)C)C

Technology Process of Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester

There total 20 articles about Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl 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: 76.0%

(1R,3R)-trans-chrysanthemic acid (4638-92-0) + (S,Z)-2-(but-2-en-1-yl)-4-hydroxy-3-methylcyclopent-2-en-1-one (3894-82-4) → (S)-3-((Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl(1R,3R) -2,2-dimethyl-3-(2-methylprop-1-en-1-yl ) -cyclopropane-1-carboxylate (25402-06-6)

Guidance literature:

(1R,3R)-trans-chrysanthemic acid; With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; In acetonitrile; at 0 - 5 ℃; for 0.5h; Inert atmosphere;

(S,Z)-2-(but-2-en-1-yl)-4-hydroxy-3-methylcyclopent-2-en-1-one; In acetonitrile; at 20 - 25 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02767

Reference yield:

(1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (4489-14-9) + (S,Z)-2-(but-2-en-1-yl)-4-hydroxy-3-methylcyclopent-2-en-1-one (3894-82-4) → (S)-3-((Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl(1R,3R) -2,2-dimethyl-3-(2-methylprop-1-en-1-yl ) -cyclopropane-1-carboxylate (25402-06-6)

Guidance literature:

at 0 ℃; for 1h; Reflux;

Reference yield:

ethyl trans-(+/-)-chrysanthemate (97-41-6,1802-02-4,7377-84-6,15543-65-4,16642-27-6,34909-55-2,41641-25-2,41641-26-3,41641-27-4) → (S)-3-((Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl(1R,3R) -2,2-dimethyl-3-(2-methylprop-1-en-1-yl ) -cyclopropane-1-carboxylate (25402-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hydroxide / ethanol; water / 3 h

2.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C

3.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere

3.2: 2 h / 20 - 25 °C / Inert atmosphere

With 1-methyl-1H-imidazole; (S)-1-(1-Naphthyl)ethylamine; p-toluenesulfonyl chloride; potassium hydroxide; In ethanol; water; acetonitrile;

DOI:10.1021/acs.joc.9b02767

upstream raw materials:

(1R,3R)-trans-chrysanthemic acid

(1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride

(S,Z)-2-(but-2-en-1-yl)-4-hydroxy-3-methylcyclopent-2-en-1-one

ethyl trans-(+/-)-chrysanthemate

Downstream raw materials:

(1R,3R)-trans-chrysanthemic acid