Methyl chrysanthemate, trans-(+)-

Base Information

• Chemical Name: Methyl chrysanthemate, trans-(+)-
• CAS No.: 24141-52-4
• Deprecated CAS: 15543-70-1
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.263
• UNII: 2Y8A8IR6JO,6GTM19T6JT
• DSSTox Substance ID: DTXSID2058338
• Nikkaji Number: J943.281G
• Mol file: 24141-52-4.mol

Synonyms:6GTM19T6JT;Methyl chrysanthemate, trans-(+)-;24141-52-4;UNII-6GTM19T6JT;2Y8A8IR6JO;Methyl chrysanthemate, trans-(1R,3R)-;(+)-trans-Chrysanthemic acid methyl ester;Methyl chrysanthemate, trans-(+/-)-;Methyl trans-3,3-dimethyl-2-(2-methyl-1-propenyl)cyclopropanecarboxylate, (+)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, methyl ester, (1R,3R)-;27335-32-6;Chrysanthemic acid methyl;UNII-2Y8A8IR6JO;Methyl chrysanthemate (trans);SCHEMBL3683341;DTXSID2058338;Cyclopropanecarboxylic acid, 2-2-dimethyl-3-(2-methyl-1-propenyl)-, methyl ester, trans-;(+/-)-TRANS-CHRYSANTHEMIC ACID METHYL ESTER;methyl trans-3,3-dimethyl-2-(2-methyl-1-propenyl)cyclopropanecarboxylate;CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPEN-1-YL)-, METHYL ESTER, (1R,3R)-REL-

Chemical Property of Methyl chrysanthemate, trans-(+)-

Chemical Property:

• Boiling Point: 205.2°Cat760mmHg
• Flash Point: 68.4°C
• PSA: 26.30000
• Density: 1.004g/cm³
• LogP: 2.39780
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 182.130679813
• Heavy Atom Count: 13
• Complexity: 247

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Methyl chrysanthemate, trans-(+)-

There total 52 articles about Methyl chrysanthemate, trans-(+)- 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: 87.0%

(1S,3S)-3-(5,5-Dimethyl-2-thioxo-[1,3]dioxolan-4-yl)-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester → methyl (dl)-trans-chrysanthemate (5460-63-9,15543-70-1,17779-27-0,22467-82-9,24141-52-4,26770-96-7,27335-32-6,55700-72-6,55701-01-4)

Guidance literature:

With phosphorous acid trimethyl ester; at 120 ℃; for 24h;

DOI:10.1016/S0040-4039(02)01270-4

Reference yield: 83.0%

methanol (67-56-1) + Phosphoric acid diethyl ester 4,4,7,7-tetramethyl-4,7-dihydro-oxepin-2-yl ester → (+/-)-cis-Chrysanthemsaeure-methylester (5460-63-9,15543-70-1,17779-27-0,22467-82-9,24141-52-4,26770-96-7,27335-32-6,55700-72-6,55701-01-4)

Guidance literature:

With triethylamine; In chloroform; at 65 ℃;

DOI:10.1021/ja00072a051

Reference yield: 83.0%

(1R,3S)-3-(5,5-Dimethyl-2-thioxo-[1,3]dioxolan-4-yl)-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester → (+/-)-cis-Chrysanthemsaeure-methylester (5460-63-9,15543-70-1,17779-27-0,22467-82-9,24141-52-4,26770-96-7,27335-32-6,55700-72-6,55701-01-4)

Guidance literature:

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; at 40 ℃; for 8h;

DOI:10.1016/S0040-4039(02)01270-4

upstream raw materials:

methanol

trans-chrysanthemic acid

chrysanthemumic acid methyl ester

sodium tert-pentoxide

Downstream raw materials:

trans-chrysanthemyl alcohol

4,5-dihydro-5-propan-2-yl-3-propan-2-ylidenefuran-2(3H)-one

(E)-3-methoxycarbonyl-2,6-dimethylhepta-1,4-diene

methyl trans-5-methyl-2-propan-2-ylidenehex-3-enoate

Refernces

• 1、 Gareev,Sultanova,Biglova,Dokichev,Tomilov. "New catalytic system Cu(OAc)2-2,4-lutidine-ZnCl2 for olefin cyclopropanation with methyl diazoacetate". experimental part. p. 1784 - 1786. Retrieved 2011/04/23.
• 2、 Krief, Alain,Jeanmart, Stephane. "Novel synthesis of (d,l) trans-chrysanthemic acid involving a β-diketone fragmentation". . p. 6167 - 6168. Retrieved 2007/10/03.