(1S,3S)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid

Base Information

• Chemical Name: (1S,3S)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid
• CAS No.: 93132-78-6
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.219
• Mol file: 93132-78-6.mol

Synonyms:(1S,3S)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid;93132-78-6

Chemical Property of (1S,3S)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.95E-05mmHg at 25°C
• Boiling Point: 316.1°Cat760mmHg
• Flash Point: 159.2°C
• Density: 1.187g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 276

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1C(C1(C)C)C(=O)O)C=O
• Isomeric SMILES: C/C(=C\[C@H]1[C@@H](C1(C)C)C(=O)O)/C=O

Technology Process of (1S,3S)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid

There total 7 articles about (1S,3S)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid 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: 59.0%

methyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate (35867-05-1) → (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid (93132-69-5,93132-78-6)

Guidance literature:

With potassium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; water; 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) → (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid (93132-69-5,93132-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyrrolidine / 1 h / 60 °C

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

With pyrrolidine; potassium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; water;

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) → (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid (93132-69-5,93132-78-6)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium hydroxide / ethanol; water / 3 h

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

3: ozone / Acidic conditions

4: pyrrolidine / 1 h / 60 °C

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

With pyrrolidine; (S)-1-(1-Naphthyl)ethylamine; ozone; potassium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; ethanol; water;

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