Chemistry of Natural Compounds p. 372 - 374 (1985)
Update date:2022-08-17
Topics:
Odinokov, V. N.
Ishmuratov, G. Yu.
Balezina, G. G.
Tolstikov, G. A.
A new route is proposed for the synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates which is based on the reaction of the Grignard reagent from the readily accessible 1-bromo-5-(1-ethoxyethoxy)pentane with 1-bromohept-3-yne - the bromide obtained from product of the β-hydroxyethylation of pent-1-yne with 2-chloroethylvinyl ether, hept-3-yn-1-ol, by a double decomposition reaction of its tosylate with lithium bromide.The key synthon - dodec-8-yn-1-ol - was converted with the aid of sodium in liquid ammonia into the stereochemical individual dodec-8E-enol, while its reduction with the aid of 9-borabicyclo<3.3.1>nonane (BBN) gave the stereoisomeric alcohol exclusively with the Z configuration, as followed from the results of capillary GLC and the IR spectra of the corresponding acetates.The PMR spectra of the compounds synthesized are also given.
View MoreYancheng Creator Chemical Co., Ltd
Contact:0086-515-88710008 88710068 88710858 88710868
Address:No.21 Renming Road, Longgang Town, Yandu County,Yancheng City
Contact:+0086-21-61984905-1
Address:Building 60,Zimian Park, LongYang industrial Area, 1515Nong,Yuandong Road Fengxian District, Shanghai ,China
Contact:+86-28-88523492
Address:714rooms of Time Square, Pujiang County
Shijiazhuang Haitian Amino Acid Co., Ltd.
Contact:+86-311-88908111
Address:Shijiazhuang Hebei province,China
Shanghai Pengkai Chemical Co.,Ltd
Contact:+86-21-60526671
Address:No.4226 Duzhuang Rd Minhang District Shanghai China
Doi:10.1021/jo971000t
(1998)Doi:10.1021/acs.organomet.5b00521
(2015)Doi:10.1016/j.tetlet.2007.08.117
(2007)Doi:10.1021/acs.biochem.9b00549
(2019)Doi:10.1007/BF00898059
(1977)Doi:10.1002/jlcr.2580140215
(1978)