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| | 11-DODECYN-1-OL Basic information |
| Product Name: | 11-DODECYN-1-OL | | Synonyms: | 11-dodecyn-1-01;11-DODECYN-1-OL;11-Dodecyne-1-ol;odec-11-yn-1-ol;Dodec-11-yn-1-ol | | CAS: | 18202-10-3 | | MF: | C12H22O | | MW: | 182.3 | | EINECS: | | | Product Categories: | | | Mol File: | 18202-10-3.mol |  |
| | 11-DODECYN-1-OL Chemical Properties |
| Melting point | 18.8°C (estimate) | | Boiling point | 285.73°C (rough estimate) | | density | 0.8530 (estimate) | | refractive index | 1.4535 (estimate) | | storage temp. | 2-8°C | | form | <26°C Solid,>28°C Liquid | | pka | 15.20±0.10(Predicted) | | color | Colorless to off-white | | InChI | InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h1,13H,3-12H2 | | InChIKey | XNRAUTMOUDUPET-UHFFFAOYSA-N | | SMILES | C(O)CCCCCCCCCC#C |
| | 11-DODECYN-1-OL Usage And Synthesis |
| Uses | 11-Dodecyn-1-ol is a synthetic intermediate of the sex pheromone (Z,E)-11,13,15-Hexadecatrienyl acetate for Thaumetopoea processionea[1]. | | Synthesis | NaH (7.5 g, 60% oil dispersion, 326 mmol) was added batchwise to a stirred 0 C solution of dodeca-3-yn-1-ol (10.0 g, 54.95 mmol; GF Smith) in ethylenediamine (40 mL).After 1 h, the temperature was raised to 70 C. The reaction mixture was cooled to 0 C for another 8 h and carefully terminated with ice-cold water (100 mL) and extracted with ether (3 x 60 mL). After another 8h, the reaction mixture was cooled to 0 C, carefully terminated with ice-cold water (100 mL) and extracted with ether (3 x 60 mL). The combined ether extracts were washed with water (100 mL). The aqueous washings were back-extracted with ether (3 x 60mL). The combined organic extracts were concentrated under vacuum and the residue was subjected to column chromatography using 10% EtOAc/hexane to obtain 11-dodecyne-1-ol (7.4 g, 74%) contaminated with 3-5% of other regioisomers (regioisomer).TLC: 30% EtOAc/hexane, Rf 0.4; 1H NMR (300 MHz, CDCl3). CDCl3) 3.66 (t, 2H, J = 7.3 Hz), 2.14-2.21 (m, 2H), 1.93 (t, J = 1.9 Hz, 1H), 1.20-1.63 (m, 16H). | | References | [1] Gries R, et al. (Z, Z)-11, 13-Hexadecadienyl acetate and (Z, E)-11, 13, 15-hexadecatrienyl acetate: synergistic sex pheromone components of oak processionary moth, Thaumetopoea processionea (Lepidoptera: Thaumetopoeidae)[J]. Chemoecology, 2004, 14: 95-100... |
| | 11-DODECYN-1-OL Preparation Products And Raw materials |
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