Looplure

Base Information

• Chemical Name: Looplure
• CAS No.: 14959-86-5
• Deprecated CAS: 105421-22-5,110413-75-7
• Molecular Formula: C14H26 O2
• Molecular Weight: 226.359
• Hs Code.: 2915390090
• European Community (EC) Number: 239-031-1
• UNII: 83U0A15960
• DSSTox Substance ID: DTXSID10884777
• Nikkaji Number: J4.077K
• Wikidata: Q27269450
• Metabolomics Workbench ID: 3889
• Mol file: 14959-86-5.mol

Synonyms:(Z)-7-dodecen-1-yl acetate;7-dodecen-1-yl acetate;7-dodecen-1-yl acetate, (trans)-isomer;cis-7-dodecen-1-ol acetate

Chemical Property of Looplure

Chemical Property:

• Vapor Pressure: 0.00114mmHg at 25°C
• Melting Point: -22.4°C (estimate)
• Refractive Index: 1.4485 (20℃)
• Boiling Point: 300.1°Cat760mmHg
• Flash Point: 96.5°C
• PSA: 26.30000
• Density: 0.881g/cm³
• LogP: 4.24640
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 226.193280068
• Heavy Atom Count: 16
• Complexity: 185

Purity/Quality:

93% ^*data from raw suppliers

(7Z)-DodecenylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCOC(=O)C
• Isomeric SMILES: CCCC/C=C\CCCCCCOC(=O)C
• Uses: Insect attractant. (7Z)-Dodecenyl Acetate is a sex pheromone of the cabbage looper Trichoplusia which is synthezied via nucleophilic substitution reaction between the Grignard reagent of the protected bromohydrin with (Z)-2-hepten-1-yl acetate in the presence of CuI catalyst.

Technology Process of Looplure

There total 76 articles about Looplure 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: 95.0%

(Z)-7-dodecenol (20056-92-2) + acetyl chloride (75-36-5) → (Z)-7-dodecenyl acetate (14959-86-5)

Guidance literature:

With pyridine; In hexane; for 2h;

DOI:10.1007/BF02495779

Reference yield: 95.0%

(Z)-7-dodecenol (20056-92-2) + acetic anhydride (108-24-7) → (Z)-7-dodecenyl acetate (14959-86-5)

Guidance literature:

With pyridine; In diethyl ether;

Reference yield: 93.0%

(Z)-1-Acetoxy-7-dodecene Oxide (28254-05-9,53248-89-8) → (Z)-7-dodecenyl acetate (14959-86-5)

Guidance literature:

With triphenylphosphine hydrogen iodide; triphenylphospine diiodide; In hexane; benzene; 1.) 24 h, 0 deg C, 2.) 24 h, room temp.;

DOI:10.1055/s-1980-29224

upstream raw materials:

Dodec-7-in-1-yl acetat

12-chloro-dodec-5c-ene

potassium acetate

Δ⁷-dodecen-1-ol

Downstream raw materials:

methyl (9E)-octadec-9-enoate

5-decene

myristelaidic acid methyl ester

(E)-7-dodecenyl acetate

Refernces

• 1、 Bykov,Goletiani,Butenko,Finkel'shtein. "Stereoselective cometathesis of 1,5-cyclooctadiene with ethylene as an efficient pathway to Z-ene biologically active natural products". . p. 163 - 166. Retrieved 2002.
• 2、 Ishmuratov, G. Yu.,Balezina, G. G.,Odinokov, V. N.,Zelenova, L. M.,Tolstikov, G. A.. "NEW ONE-STEP PATH FOR STEREOSPECIFIC SYNTHESIS OF (Z)-ALKEN-1-OLS FROM ACETYLENIC ALDEHYDES". . p. 609 - 610. Retrieved 1983.
• 3、 Horiike,Hirano. "A facile synthesis of the sex pheromones (Z)-7-dodecen-1-yl acetate and its homologues". . p. 2229 - 2230. Retrieved 1980.
• 4、 Nguyen, Thanh-Danh,Nguyen, Cong-Hao,Im, Chan,Dang, Chi-Hien. "A Facile Synthesis of the Sex Pheromone of the Cabbage Looper Trichoplusia ni". . p. 877 - 879. Retrieved 2016.
• 5、 Browne, Duncan L.,Colombel-Rouen, Sophie,Crévisy, Christophe,Curbet, Idriss,Mauduit, Marc,McBride, Tom,Morvan, Jennifer,Roisnel, Thierry. "Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**". supporting information. p. 19685 - 19690. Retrieved 2021/08/06.
• 6、 -. "Synthesis of (Z)-7-dodecylene-1-alcohol and acetic ester thereof". Paragraph 0025-0027. . Retrieved 2019/02/06.