3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate

Base Information

• Chemical Name: 3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate
• CAS No.: 121-20-0
• Molecular Formula: C21H28 O5
• Molecular Weight: 360.45
• Mol file: 121-20-0.mol

Synonyms:Cinerin II(6CI); Cyclopropaneacrylic acid, 3-carboxy-a,2,2-trimethyl-, (Z)-(1R,3R)-1-methyl ester, esterwith (Z)-(R)-2-(2-butenyl)-4-hydroxy-3-methyl-2-cyclopenten-1-one (8CI);Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-,3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester, [1R-[1a[S*(Z)],3b(E)]]-; Cyclopropanecarboxylicacid, 3-[(1E)-3-methoxy-2-methyl-3-oxo-1-propenyl]-2,2-dimethyl-,(1S)-3-(2Z)-2-butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)- (9CI);2-Cyclopenten-1-one, 2-(2-butenyl)-4-hydroxy-3-methyl-, (Z)-(R)-, 3-ester with(Z)-(1R,3R)-3-carboxy-a,2,2-trimethylcyclopropaneacrylic acid, 1-methyl ester (8CI)

Chemical Property of 3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate

Chemical Property:

• Vapor Pressure: 2.01E-08mmHg at 25°C
• Refractive Index: nD20 1.5183
• Boiling Point: 453.8°Cat760mmHg
• Flash Point: 195.3°C
• PSA: 83.50000
• Density: 1.12g/cm³
• LogP: 2.36970

Purity/Quality:

99% ^*data from raw suppliers

CinerinII ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An active insecticidal constituent of pyrethrum flowers. Oxidizes rapidly and becomes inactive in presence of air. Insecticide.

Technology Process of 3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate

There total 15 articles about 3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate 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: 63.0%

C20H26O5 + methyl iodide (74-88-4) → cinerin II (121-20-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 25 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02767

Reference yield:

methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate (27335-33-7) → cinerin II (121-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyrrolidine / 1 h / 60 °C

2.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere

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

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

4.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C

5.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 - 25 °C / Inert atmosphere

With pyrrolidine; 1-methyl-1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium carbonate; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; potassium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/acs.joc.9b02767

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) → cinerin II (121-20-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium hydroxide / ethanol; water / 3 h

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

3.1: ozone / Acidic conditions

4.1: pyrrolidine / 1 h / 60 °C

5.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere

6.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere

6.2: 2 h / 20 - 25 °C / Inert atmosphere

7.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C

8.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 - 25 °C / Inert atmosphere

With pyrrolidine; 1-methyl-1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; (S)-1-(1-Naphthyl)ethylamine; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; potassium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; ethanol; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/acs.joc.9b02767

upstream raw materials:

methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate

ethyl trans-(+/-)-chrysanthemate

trans-chrysanthemic acid

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

Refernces