(-)-cis-Chrysanthemic acid

Base Information

• Chemical Name: (-)-cis-Chrysanthemic acid
• CAS No.: 2935-23-1
• Molecular Formula: C10H16 O2
• Molecular Weight: 168.236
• European Community (EC) Number: 247-994-4,633-864-8
• UNII: TFK3B71TRY
• DSSTox Substance ID: DTXSID60885370
• Nikkaji Number: J232.118A
• Wikidata: Q27118140
• Metabolomics Workbench ID: 28033
• Mol file: 2935-23-1.mol

Synonyms:(-)-cis-Chrysanthemic acid;26771-06-2;(-)-cis-Chrysanthemumsaeure;Chrysanthemic acid, cis-(-)-;cis-Chrysanthemic Acid;(1S-cis)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;cis-Chrysanthemum Monocarboxylic acid;UNII-TFK3B71TRY;TFK3B71TRY;cis-(-)-chrysanthemic acid;(1S-cis)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;EINECS 247-994-4;(1S,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S,3R)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (1S,3R)-;BRN 2326292;(1S,3R)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;(1S,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylic acid;Cis-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid;4-09-00-00168 (Beilstein Handbook Reference);EINECS 225-067-5;BRN 2043419;cis chrysanthemic acid;SCHEMBL3249546;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, cis-;CHEBI:39105;DTXSID60885370;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R-trans)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1S,3R)-;CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, (1R,3R)-(+)-;CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, (1S-cis)-;CHRYSANTHEMIC ACID L-CIS-FORM;AKOS015892868;LMPR0102060003;LS-58670;W18744;Q27118140;2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid #;2,2-Dimethyl-3-(E)-.alpha.-(2-methylallyl)cyclopropanecarboxylic acid;Cis-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylicacid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, cis-;2,2-Dimethyl-3alpha-(2-methyl-1-propenyl)-1alpha-cyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S-cis)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1R,3R)-

Chemical Property of (-)-cis-Chrysanthemic acid

Chemical Property:

• Melting Point: 115-116°
• Boiling Point: 246.4°Cat760mmHg
• Flash Point: 119°C
• PSA: 37.30000
• Density: 1.077g/cm³
• LogP: 2.30940
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (-)-cis-Chrysanthemic acid

There total 141 articles about (-)-cis-Chrysanthemic 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: 86.0%

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) → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 3h;

DOI:10.1021/acs.joc.9b02767

Reference yield: 73.0%

tert-amyl trans-chrysanthemate (78715-54-5) → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With potassium hydroxide; In ethanol; for 24h; Heating;

DOI:10.1021/jo00335a002

Reference yield: 63.0%

N-[trans-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarbonyloxy]-5-(4-methoxyphenyl)-4-methylthiazole-2(3H)-thione → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With cyclohexa-1,4-diene; In benzene; at 20 ℃; for 7.5h; Photolysis;

DOI:10.1055/s-0029-1217102

upstream raw materials:

2,5-Dimethyl-2,4-hexadiene

(+/-)-3t-(β-chloro-isobutyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid

(+/-)-trans-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile

(+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide

Downstream raw materials:

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

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

(+/-)-trans-Homochrysanthemsaeure

(+/-)-trans-(E)-pyrethricsaeure

Refernces

• 1、 Krief, Alain,Kremer, Adrian. "Stereochemical issues on the fragmentation of non-enolisable β-heterosubstituted-cyclopentanones with wet and anhydrous potassium hydroxide". . p. 3045 - 3049. Retrieved 2010.
• 2、 Ashida, Yuichiro,Kawamoto, Momoyo,Matsuo, Noritada,Moriyama, Mizuki,Tanabe, Yoo. "Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods". . p. 2984 - 2999. Retrieved 2020/03/24.
• 3、 Miller, David C.,Choi, Gilbert J.,Orbe, Hudson S.,Knowles, Robert R.. "Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer". supporting information. p. 13492 - 13495. Retrieved 2015/11/09.