56578-18-8Relevant articles and documents
Method for synthesizing sex pheromone of anarsia lineatella
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, (2020/05/30)
The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing sex pheromone of anarsia lineatella. The method comprises the following steps:with 5-hexyn-1-ol as a raw material, subjecting 5-hexyn-1-ol and1-bromobutane to a nucleophilic substitution reaction in the presence of n-butyllithium and HMPA to generate 5-decyn-1-ol, then performing reduction via lithium aluminum hydride to obtain (E)-5-decen-1-ol, and finally performing an acetylation reaction to obtain (E)-5-decen-1-ol acetate. According to the invention, a triple bond of alkyne is reduced into an E-type double bond by lithium aluminum hydride, so the method has the advantages of simple synthetic route, mild reaction conditions, good environmental compatibility and the like.
Enantioselective Aza-Heck Cyclizations of N-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines
Ma, Xiaofeng,Hazelden, Ian R.,Langer, Thomas,Munday, Rachel H.,Bower, John F.
supporting information, p. 3356 - 3360 (2019/03/07)
Pd(0)-systems modified with SPINOL-derived phosphoramidate ligands promote highly enantioselective aza-Heck cyclizations of alkenyl N-(tosyloxy)carbamates. The method provides versatile access to challenging N-heterocycles and represents the broadest scope enantioselective aza-Heck protocol developed to date.
Synthesizing method for 5E-decene-1-alcohol and acetic acid 5E-decenoate
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, (2017/04/03)
The invention provides a synthesizing method for 5E-decene-1-alcohol and acetic acid 5E-decenoate. With acrylaldehyde and acetylene being raw materials, a coupling reaction is carried out under the existence of a palladium catalyst to obtain 5-bromo-4E-pentenal, 5-bromo-4E-pentenal and methoxy methyl-triphenyl phosphonium chloride are subjected to a Wittig reaction to obtain 1E,5E-1-bromo-6-methoxy hexadiene, then 1E,5E-1-bromo-6-methoxy hexadiene and butyl magnesium bromide are subjected to a Kumada coupling reaction to obtain 1E,5E-1-methoxy decadiene, 5E-decenal is obtained through hydrolysis, then 5E-decene-1-alcohol is obtained through reducing, and finally the acetic acid 5E-decenyl acetate is obtained after esterification. The raw materials used for synthesis are low in price and easy to obtain, the synthesizing route is simple, reaction conditions are mild, operation is convenient and safe, industrialized production is easy, the yield is high, and the synthesizing method has important meaning for prevention and treatment of anarsia lineatella.
SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
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, (2016/01/30)
In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol
Kim, Hee Jin,Su, Liang,Jung, Heejung,Koo, Sangho
supporting information; experimental part, p. 2682 - 2685 (2011/06/26)
Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl 2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
A selective Ru-catalyzed semireduction of alkynes to Z olefins under transfer-hydrogenation conditions
Belger, Christian,Neisius, N. Matthias,Plietker, Bernd
supporting information; experimental part, p. 12214 - 12220 (2011/03/17)
By using a readily available, air- and moisture-stable dihydrido-Ru complex, a variety of Z olefins are accessible under transfer-hydrogenation conditions with formic acid as the hydrogen source in excellent yields and Z/E selectivities. A discerning transformation: Z-Configured C=C bonds are stereoselectively formed from alkynes in the presence of a Ru catalyst with formic acid as the sole H2 source at room temperature (see scheme). A variety of functional groups are compatible with this novel procedure. Operational simplicity and the lack of overreduction products are characteristics for this unprecedented process.
Biologically active compounds by catalytic olefin metathesis
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, (2008/06/13)
Biologically active compounds such as pheromones and precursors thereof are produced by catalyzed cross metathesis of dissimilar terminal olefins or of a cyclodiene and a terminal olefin.
Preparation of alkenols
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, (2008/06/13)
A process for preparing alkenols of the formula I where R1 is hydrogen or a hydrocarbon radical, and n is an integer from 3 to 15, a) by reacting a phosphonium salt of the formula IIa where X is chlorine, bromine or iodine, with an aldehyde of the formula IIIa or its hemiacetal of the formula IIIb STR1 or b) by reacting a phosphonium salt of the formula IIb with a aldehyde of the formula IV in a solvent in the presence of a base, wherein the base is the alkali metal salt of an alcohol and the solvent is an alcohol.
Reactions of α-epoxysilanes with organocopper reagents. A stereoselective route to alkenes
Chauret, Denise C.,Chong, J. Michael
, p. 3695 - 3698 (2007/10/02)
Reactions of α-epoxysilanes with cuprate reagents can be controlled to give β-silyl alcohols as major products. An oxidation, Grignard addition, and elimination sequence then provides alkenes with up to 98% de.
Metal/Ammonia Reduction of Ethers of 3-Decyn-1-ol: Effects of Structure and Conditions on Cleavage and Rearrangement
Doolittle, Robert E.,Patrick, Delrea G.,Heath, Robert H.
, p. 5063 - 5066 (2007/10/02)
Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether.Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers.The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.
