Methyl (+)-cis-chrysanthemate

Base Information

• Chemical Name: Methyl (+)-cis-chrysanthemate
• CAS No.: 55701-01-4
• Molecular Formula: C11H18O2
• Molecular Weight: 182.263
• European Community (EC) Number: 435-450-0
• UNII: EVL8AMM8PH,RU079KN7CR
• DSSTox Substance ID: DTXSID301132992
• Nikkaji Number: J1.787.148J
• Mol file: 55701-01-4.mol

Synonyms:EVL8AMM8PH;RU079KN7CR;Methyl (+)-cis-chrysanthemate;Methyl (+/-)-cis-chrysanthemate;Methyl chrysanthemate, cis-(+)-;Methyl chrysanthemate, cis-(+/-)-;(+)-cis-Chrysanthemic acid methyl ester;(+/-)-cis-Chrysanthemic acid methyl ester;17779-27-0;55701-01-4;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, methyl ester, (1R,3S)-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, methyl ester, (1R,3S)-rel-;UNII-EVL8AMM8PH;UNII-RU079KN7CR;DTXSID301132992;2alpha-(2-Methyl-1-propenyl)-3,3-dimethylcyclopropane-1alpha-carboxylic acid methyl ester;rel-Methyl (1R,3S)-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate

Chemical Property of Methyl (+)-cis-chrysanthemate

Chemical Property:

• Boiling Point: 90 °C (10 mmHg)
• PSA: 26.30000
• 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:

SDS file from LookChem

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 (+)-cis-chrysanthemate

There total 52 articles about Methyl (+)-cis-chrysanthemate 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:

(1R)-cis-chrysanthemic acid

(+/-)-Casbene

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

trans-chrysanthemic acid