- Dihydrotestosterone derivatives: Relative binding affinity versus affinity purification
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Mono esters of a homologous series of diacids of dihydrotestosterone were synthesized and converted to the corresponding n-butyl amides. The relative binding affinities of these amides to androgen receptor were compared with the degree of purification of rat prostate androgen receptor by affinity columns prepared by linking the steroidal acid to ammo Sepharose. There was good correlation between binding of the amide model to androgen receptor and the extent of purification by the affinity resin.
- Stobaugh, Mark E.,Blickenstaff, Robert T.
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Read Online
- Preparation method of 2-(6-chlorohexyloxy) tetrahydro-2H-pyran
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The invention provides a preparation method of 2-(6-chlorohexyloxy) tetrahydro-2H-pyran, which is characterized by comprising the steps of synthesis of 2-(6-chlorohexyloxy) tetrahydro-2H-pyran, and purification of 2-(6-chlorohexyloxy) tetrahydro-2H-pyran. The synthesis method of 2-(6-chlorohexyloxy) tetrahydro-2H-pyran comprises the steps of S1, mixing 6-chloro-1-hexanol, a catalyst and toluene ina 500ml three-neck reaction flask at the temperature of 0-30 DEG C; S2, adding 3,4-dihydropyran into the mixture obtained in the step S1, and adjusting the reaction temperature to 10-50 DEG C to obtain a reaction product; and S3, purifying the reaction product obtained in the step S2 to obtain a pure product of 2-(6-chlorohexyloxy) tetrahydro-2H-pyran. According to the method, a proper catalyst and optional methylbenzene are used as solvents, and the molar ratio of reactants is controlled, so that the technical effects that the yield is high, the consumption of organic solvents is low, and the catalyst is easily removed from a system after reaction can be achieved.
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Paragraph 0038-0063
(2021/01/12)
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- Method for preparing 8 -methyldialdehyde
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To the preparation method of 8 - chloro 6 - hexanol, the hydroxyl is firstly protected with the dihydropyran under the catalysis of p-toluenesulfonic acid, and -1 -chloro 6 -hexyl tetrahydropyranyl is obtained. 6 -chloro -hexyl tetrahydropyranyl ether is reacted with magnesium chips to form a formative reagent and reacted with 1 - bromo -2 - methyl - butane under the catalysis of cuprous bromide to obtain the intermediate 8 - methyl -tetrahydropyran ether. The intermediates do not need to be purified, and the hydroxyl group is removed directly under acidic conditions to obtain 8 - methyl -1 - sunflower. Finally, 2, 2, 6 and 6 - tetramethylpiperidine are oxidized to obtain the product 8 - methyldialdehyde. The synthesis process uses common reagents, is low in cost, mild in reaction conditions and high in yield, is suitable for large-scale industrial production, and has a good application prospect in the field of food additives.
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Paragraph 0044-0047; 0054-0057; 0064-0067
(2021/11/03)
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- Process synthesis method for fatty alcohol hydroxyl protection by adopting micro-reactor
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The invention provides a process synthesis method for protecting fatty alcohol hydroxyl by adopting a micro-reactor. The process synthesis method comprises the following steps: S1, adjusting the temperature in the micro-reactor to 10-70 DEG C through a high-low temperature circulating tank; S2, immersing material suction pipe openings of a constant flow pump in straight-chain n-halohydrin and 3, 4-dihydropyran respectively, and setting the flow speed of the straight-chain n-halohydrin constant flow pump to be 15-45 mol/min, wherein the molar ratio of the 3, 4-dihydropyran to the straight-chainn-halohydrin ranges from 1.02 to 1.15; S3, feeding reactants into a micro-reactor, and receiving a crude product by adopting a container filled with a quenching agent after running for 4 minutes; andS4, separating and purifying the received crude product to obtain the product. By applying the micro-channel reactor, the conversion rate can be effectively increased, and the yield is increased from65-71% of the traditional reaction yield to 96% or above. No waste solvent is generated in the reaction process, no waste water is discharged, and continuous automatic production can be achieved.
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Paragraph 0030-0079
(2021/01/11)
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- ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS
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The disclosure relates to anti-cancer compounds which are anti-cancer PARP inhibitors of formula Al, A2, A3 or A4 conjugated by a linker to a steroid, whereby the steroid targets the conjugate to the nucleus, as well as to methods for their preparation and use. (I)
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Page/Page column 123-124; 142-143
(2021/05/21)
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- Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates
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The development of a stereospecific hydroxymethylation of alkyl tosylates using an inexpensive, first-row catalyst is described. The transformation proceeds under mild conditions with low pressure to deliver homologated alcohols as products. Chiral, nonracemic β-branched primary alcohols are obtained with high enantiospecificity from easily accessed secondary alkyl substrates. Simple modification of the reaction system also permits access to α-d2 alcohols. These studies use anionic metal carbonyl catalysis to access a synthetic equivalent of the challenging hydroxymethyl anion from carbon monoxide.
- Shenouda, Hannah,Alexanian, Erik J.
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supporting information
p. 9268 - 9271
(2019/11/19)
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- ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS
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The disclosure relates to anti-cancer compounds derived from nuclear steroid receptor binders, to products containing the same, as well as to methods of their use and preparation.
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Page/Page column 195; 196; 203; 204; 237; 238; 245
(2019/12/04)
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- Cyclopropenium Enhanced Thiourea Catalysis
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An integral part of modern organocatalysis is the development and application of thiourea catalysts. Here, as part of our program aimed at developing cyclopropenium catalysts, the synthesis of a thiourea-cyclopropenium organocatalyst with both cationic hydrogen-bond donor and electrostatic character is reported. The utility of the this thiourea organocatalyst is showcased in pyranylation reactions employing phenols, primary, secondary, and tertiary alcohols under operationally simple and mild reaction conditions for a broad substrate scope. The addition of benzoic acid as a co-catalyst facilitating cooperative Br?nsted acid catalysis was found to be valuable for reactions involving phenols and higher substituted alcohols. Mechanistic investigations, including kinetic and 1H NMR binding studies in conjunction with density function theory calculations, are described that collectively support a Br?nsted acid mode of catalysis.
- Smajlagic, Ivor,Durán, Rocio,Pilkington, Melanie,Dudding, Travis
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supporting information
p. 13973 - 13980
(2018/11/21)
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- Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents
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The application of heterogeneous catalysis and green solvents to the set up of widely employed reactions is a challenge in contemporary organic chemistry. We applied such an approach to the synthesis and further conversion of tetrahydropyranyl ethers, an important class of compounds widely employed in multistep syntheses. Several alcohols and phenols were almost quantitatively converted into the corresponding tetrahydropyranyl ethers in cyclopentyl methyl ether or 2-methyltetrahydrofuran employing NH4HSO4 supported on SiO2 as a recyclable acidic catalyst. Easy work up of the reaction mixtures and the versatility of the solvents allowed further conversion of the reaction products under one-pot reaction conditions.
- Azzena, Ugo,Carraro, Massimo,Modugno, Gloria,Pisano, Luisa,Urtis, Luigi
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supporting information
p. 1655 - 1659
(2018/07/25)
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- Manufacturing method for substrate having liquid crystal alignment film for in-plane switching-type liquid crystal display element
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The present invention provides an in-plane switching-type liquid crystal display element imparted with a high-efficiency alignment control function, and having excellent burn-in properties. The present invention also provides a manufacturing method for a substrate having a liquid crystal alignment film, said method having the following steps for obtaining a liquid crystal alignment film for an in-plane switching-type liquid crystal display element imparted with an alignment control function: [I] a step in which a polymer composition, which contains (A) a light-sensitive sidechain polymer that exhibits liquid crystallinity at a prescribed temperature range and (B) an organic solvent, is coated on a substrate having a conductive film for in-plane switching, and a coating film is formed; [II] a step in which the coating film obtained in [I] is irradiated with polarized UV light; and [III] a step in which the coating film obtain in [II] is heated.
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Paragraph 0683; 0685-0687
(2018/03/24)
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- POLYMERIZABLE COMPOUND AND OPTICAL ANISOTROPIC BODY
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PROBLEM TO BE SOLVED: To provide a polymerizable compound that prevents the occurrence of crystal deposition or the like when added to a polymerizable composition and has high storage stability. SOLUTION: This invention provides a compound represented by general formula (I), specifically, a compound of the following structure. This invention also provides a composition comprising the compound, a polymer obtained by polymerization of the composition and an optical anisotropic body using the polymer. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0167; 0168
(2016/10/09)
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- MESOGEN CONTAINING COMPOUNDS
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Compounds including at least one mesogenic substructure and at least one long flexible segment and methods of synthesizing the same are disclosed. Formulations which include various embodiments of the mesogen containing compounds and their use in articles of manufacture and ophthalmic devices are also disclosed.
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Page/Page column 58
(2010/01/31)
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- Improved synthesis of unique estradiol-linked platinum(II) complexes showing potent cytocidal activity and affinity for the estrogen receptor alpha and beta
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We have recently reported the synthesis of a platinum(II) complex, made of estradiol, the female sex hormone, and a cisplatin analog, an anticancer drug, linked together by an eleven carbon atoms chain. The novel estradiol-Pt(II) hybrid molecule was synthesized in nine chemical steps with 10% overall yield. This new compound has been tested in vitro on estrogen-dependent (MCF-7) and -independent (MDA-MD-231) (ER+ and ER-) cell lines. Interestingly, the biological activity was quite significant, more potent than that of cisplatin, the compound currently used in chemotherapy. The estrogen receptor binding affinity (ERBA) of this compound was very similar to that of 17β-estradiol (E2) on both estrogen receptors (ERs), α and β. In order to further study this type of molecule, we have decided to synthesize several analogs with the same estrogenic scaffold but with various chain lengths separating the estradiol from the toxic part of the molecule. This was planned in order to study the effect of the length of the linking chain on the biological activity of the hybrids. Four E2-Pt(II) hybrid molecules having 6-14 carbon atoms linking chain have been synthesized using a new synthetic methodology. They are synthesized in only eight chemical steps with 21% overall yield. The 17β-estradiol-linked platinum(II) complexes have been tested for their receptor binding affinity as well as for their cytocidal activity on several breast cancer cell lines. The synthesis and biological results are reported herein.
- Descoteaux, Caroline,Leblanc, Valerie,Belanger, Geoffroy,Parent, Sophie,Asselin, Eric,Berube, Gervais
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p. 1077 - 1089
(2008/12/22)
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- Novel Imaging Agents for Fibrosis
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The present invention provides a novel imaging agent targeting the mannose-6-phosphate (M6P) receptor suitable for the non-invasive visualization of fibrosis. A method for the preparation of the imaging agent is also provided by the invention, as well as a precursor for use in said method. The invention also provides a pharmaceutical composition comprising the imaging agent and a kit for the preparation of the pharmaceutical composition. In a further aspect, use of the imaging agent for in vivo imaging and in the preparation of a medicament for the diagnosis of a condition in which the mannose-6-phosphate receptor is upregulated is provided.
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- NOVEL IMAGING AGENTS
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The present invention provides a novel imaging agent suitable for the non-invasive visualization of fibrosis. A precursor for the preparation of the imaging agent is also provided by the invention, as well as a pharmaceutical composition comprising the im
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Page/Page column 42-43
(2008/06/13)
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- NEW HEXAFLUOROALCOHOL-BASED MONOMERS AND PROCESSES OF PREPARATION THEREOF
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The present invention relates to compounds of formula (I): wherein R1 is H, or a C1-C10 linear, branched or cyclic alkyl group which is unsubstituted or substituted with fluorine; R2 is an alicyclic group having 5 to 20 carbon atoms which is unsubstituted or substituted with fluorine; and R3 represents a C1-C10 linear or branched alkylène which is unsubstituted or substituted with fluorine. Processes for preparing such compounds are also disclosed. The compounds of the present invention can be used as monomers in the fields of photolithography and semiconductor fabrication.
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Page/Page column 12-13
(2008/06/13)
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- Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum
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A series of new chemosensitizers (modulators) against chloroquine-resistant Plasmodium falciparum were designed and synthesized in an attempt to fabricate modulators with enhancing drug-resistant reversing efficacy and minimal side effects. Four aromatic amine ring systems phenothiazine, iminodibenzyl, iminostilbene, and diphenylamine-were examined. Various tertiary amino groups including either noncyclic or cyclic aliphatic amines were introduced to explore the steric tolerance at the end of the side chain. The new compounds showed better drug-resistant reversing activity in chloroquine-resistant than in mefloquine-resistant cell lines and were generally more effective against chloroquine-resistant P. falciparum isolates from Southeast Asian (W2 and TM91C235) than those from South America (PC49 and RCS). Structure-activity relationship studies revealed that elongation of the alkyl side chain of the molecule retained the chemosensitizing activity, and analogues with four-carbon side chains showed superior activity. Furthermore, new modulators with phenothiazine ring exhibited the best chemosensitizing activity among the four different ring systems examined. Terminal amino function has limited steric tolerance as evidenced by the dramatic lose of the modulating activity, when the size of substituent at the amino group increases. The best new modulator synthesized in this study possesses all three optimized structural features, which consist of a phenothiazine ring and a pyrrolidinyl group joined by a four-carbon alkyl bridge. The fractional inhibitory concentration (FIC) index of the best compound is 0.21, which is superior to that of verapamil (0.51), one of the best-known multi-drug-resistant reversing agents. Some of the analogues displayed moderate intrinsic in vitro antimalarial activity against a W-2 clone of P. falciparum.
- Guan, Jian,Kyle, Dennis E.,Gerena, Lucia,Zhang, Quan,Milhous, Wilbur K.,Lin, Ai J.
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p. 2741 - 2748
(2007/10/03)
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- Dichroic mixture
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A mesogenic, crosslinkable mixture comprising at least one polymerisable liquid crystal and at least one polymerisable dichroic dye of the general formula I: whereinArepresents a dichroic residue exhibiting at least partial absorption in the visible region > 400 nm;n1, n2, n3, n4signifies 0 or 1 whereby the sum of n1, n2, n3 and n4 is >0, andB1 to B4represent a group of substructure II wherein the broken line symbolises the linkage to said dichroic residue.
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- New and simple syntheses of the attractants of the female melon fly, dacus cucurbitee
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The attractant of the female melon fly, (E)-6-nonenyl acetate, and the two analogs, (E)-7-dodecenyl acetate and (E)-7-decenyl acetate were synthesized via hydrozirconation to control the regioselective coupling reactions and resulted in good yields.
- Yen, Yao-Pin,Chen, Pao-Hsing
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- A Novel Approach to Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors Based on the Link of 1,3-Dioxane-Thromboxane Receptor Antagonists and -Thromboxane Synthase Inhibitors
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A new class of dual-acting racemic thromboxane receptor antagonist/thromboxane synthase inhibitors is reported, based on the novel approach of linking the known thromboxane synthase inhibitors (TXSI) dazoxiben (2) or isbogrel (11) (separately) to thromboxane receptor antagonists (TXRA) from the 1,3-dioxane series, such as ICI 192605 (10).Dual activity was observed in vitro with inhibition of human microsomal thromboxane synthase in the range IC50 = 0.01-1.0 μM and receptor antagonist activity by inhibition of U46619-induced human platelet aggregation in the range pA2 = 5.5-7.0.The in vitro results also showed that very large groups could be tolerated at the selected substitution positions of the TXRA and TXSI components.Oral activity was observed in ex vivo tests in both rats and dogs at a dose of 10 mg/kg.Thus, (E)-7--4-(2-hydroxyphenyl)-1,3-dioxan-2-yl>benzyl>oxy>phenyl>-7-(3-pyridyl)hept-6-enoic acid (110) was both an antagonist (pA2 = 6.7) and a synthase inhibitor (IC50 = 0.02 μM)).On oral dosing (10 mg/kg) to rats and dogs, 110 showed significant TXRA activity 64 (rat, 3 h) and >59 +/- 11.3 (dog, 2 h) vs ex vivo U46619-induced platelet aggregation>.Inhibition of thromboxane synthase at the respective time points in these experiments was 81 +/- 4.4percent (rat) and 69 +/- 4.8percent (dog).
- Ackerley, Norman,Brewster, Andrew G.,Brown, George R.,Clarke, David S.,Foubister, Alan J.,et al.
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p. 1608 - 1628
(2007/10/02)
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- SYNTHESE ET ETUDE ELECTROCHIMIQUE D'ALCOOLS ET D'ESTERS DERIVES DE 3-ALKYL THIOPHENES
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Starting from 3-bromothiophene, ω-(3-thienyl)alkan-1-ols and ω-(3-thienyl)alkyl esters are obtained.Electrochemical characteristics and polymerization are described and discussed.Key words: ω-(3-thienyl)alkanols and ω-(3-thienyl)alkyl esters, electrochemical polymerization.
- Blanchetiere, D.,Noyere, C.,Catel, J.,Andrieu, C. G.,Ebel, M.
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- Quaternary ammonium compounds having muscle relaxation activity
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A quaternary ammonium having a muscle relaxation activity compound represented by the formula (I): STR1 wherein R1 represents a methylene, a lower alkylenoxy, a lower alkenylene, a lower alkynylene, --CO--, --COO--, a lower alkylene carbonyloxy, --CH(OR5)--, a lower alkylenecarbonyl, a hydroxy lower alkylene, --O--, --S--, --SO--, or --SO2 --; R2 represents a hydrogen atom, a hydroxy lower alkyl, an aldehyde, a lower alkyl carbonyl, --NO2, or --NHR6 ; R3 represents a hydrogen atom of a group --R1 --(CH2)a --[CH(CH2 A)--CH2 ]b --A; R4 represents an anion; R5 and R6 represent a hydrogen atom or a acetyl; A represents a quaternary ammonium group; a represents an integer of 1 to 8; b represents 0 or 1; m represents an integer of 1 to 4; and (Z) represents a trivalent benzene ring, a trivalent naphthalene ring, a trivalent diphenyl or a trivalent ethane radical.
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- Synthesis of Various New Nitroxide Free Radical Fatty Acids
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A generally applicable method is presented for the synthesis of various new nitroxide fatty acid isomers in which the fatty acid chains are attached at different positions of the pyrrolidin-1-oxyl ring.These isomers can be obtained by Michael addition of a nitroalkane to an α,β-unsaturated ketone to give a γ-nitro ketone, followed by ring closure with zinc and ammonium chloride to give a 1-pyrroline N-oxide which then reacts with Grignard reagents to give a pyrrolidin-1-oxyl free radical compound, which undergoes phase transfer oxidation of its terminal unsaturated bond.
- Hideg, Kalman,Lex, Laszlo
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p. 1431 - 1438
(2007/10/02)
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- A FACILE METHOD FOR THE CONVERSION OF PRIMARY ALKYL CHLORIDES TO THE CORRESPONDING BROMIDES
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Treatment of several representative primary alkyl chlorides with one equivalent of sodium bromide in 2:1 (v/v) N,N-dimethylformamide : dibromoethane at 100 deg C for several hours resulted in their quantitative conversion to the corresponding bromides.
- Babler, James H.,Spina, Kenneth P.
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p. 1313 - 1320
(2007/10/02)
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- ETUDE DES INTERACTIONS ENTRE FONCTIONS ALCOOL ET AMINE: EVOLUTION THERMIQUE D'HYDROXYDES ET DE SELS D'ω-TRIALKYLAMMONIO ALCANOLS-1
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The thermolysis of ω-hydroxyalkyltrialkylammonium hydroxides (Φ=4-8) was investigated: Elimination to alkenol competes with substitution to amino alcohol; the hydroxy group can be alkylated into aliphatic ethers by an intermolecular process; the intramolecular cyclization into cyclic ethers is important only when ω=4.Substitution reaction in amino alcohols is the main pathway for the thermolysis of ω-hydroxyalkyltrimethylammonium acetates (ω=5,6) and chloride (ω=6).
- Barbry, Didier,Hasiak, Bruno
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p. 1734 - 1744
(2007/10/02)
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- Une synthese courte et stereoselective de l'Acetoxy-1 hexadecane-13 (Z)yne-11 : Principal constituant de la secretion pheromonale produite par la femelle vierge de la Processionnaire du pin Theumetopoes pityocampa (Danis et Schiff.) (Lepidoptera notodontides).
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Resume : Une synthese courte et stereoselective de la pheromone sexuelle de la Processionnaire du pin : Thaumatopoes pityocamps (Denis et Schiff.) a ete realisee.Cette synthese utilise dans son etape finale une reaction de couplage d'un acetate ω-acetylenique sur un halogenure vinylique dans le benzene en presence de quantites catalytiques de tetrakis(triphenylphosphine)palladium et d'iodure cuivreux.
- Michelot, Didier,Guerrero, Angel,Ratovelomanana, Victorin
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p. 1043 - 1051
(2007/10/02)
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- Long Chain Phenols. Part 17. The Synthesis of 5-resorcinol, 'Cardol monoene,' and of 5-resorcinol Dimethyl Ether, 'Cardol diene' Dimethyl Ether
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Two unsaturated compounds in the 'cardol' series, an important component phenol from Anacardium Occidentale, have been synthesised. 3,5-Dimethoxybenzaldehyde interacted with OH-protected 6-chlorohexan-1-ol in the presence of lithium to give, after acidic treatment, 1-(3,5-dimethoxyphenyl)heptane-1,7-diol which was hydrogenolysed selectively to 7-(3,5-dimethoxyphenyl)heptan-1-ol.Conversion into the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene.Dmethylation with lithium iodide gave 5-resorcinol which was identical to 'cardol monoene'.Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment 10-(3,5-dimethoxyphenyl)dec-2-yn-1-ol, the bromide of which with pent-1-ynylmagnesium bromide afforded 5-pentadec-8,11-diynylresorcinol dimethyl ether.Selective hydrogenation yielded 5-resorcinol dimethyl ether identical with the dimethyl ether of 'cardol diene.'
- Baylis, Christopher J.,Odle, Stanley W.,Tyman, John H. P.
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p. 132 - 141
(2007/10/02)
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- SYNTHESIS OF BIFUNCTIONAL SPIN LABEL MOLECULES AND THEIR ORIENTATIONS IN MEMBRANES
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The synthesis of new derivatives of substituted pyrrolidine nitroxide free radicals is reported.The molecules are hydrophobic and bifunctional.A preliminary study of their orientation in lipid model membranes has been made by EPR.Molecules having chains of up to 17 atoms and polar end groups take up a conformation in membranes which is tentatively assigned to a bent configuration with both functional groups on one side of the membrane.These molecules are synthetic precursors of spin-labeled cross-linking reagents for membrane proteins.
- Tse-Tang, Man Wing,Gaffney, Betty Jean,Kelly, Robert E.
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p. 965 - 974
(2007/10/02)
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- INSECT SEX PHEROMONES. STEREOSELECTIVE SYNTHESIS OF SEVERAL (Z)- AND (E)-ALKEN-1-OLS, THEIR ACETATES, AND OF (9Z,12E)-9,12-TETRADECADIEN-1-YL ACETATE
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Several female sex pheromone components produced by moths belonging to the order of Lepidoptera, and potential attractants of Dacus oleae (Diptera:Tripetidae) have been synthesized in high chemical and stereoisomeric purity by improved acetylenic routes involving alkylation of lithium 1-alkyn-1-ides in HMPT, followed by (Z) and (E) highly stereoselective reduction of the derived internal alkynes.Particular care has been paid to optimize the parameters of the reactions used and to evaluate the chemical and isomeric purity of the reaction products.The compounds synthesized include (Z)- and (E)-5-nonen-1-ol, (Z)- and (E)-7-dodecen-1-yl acetate, (Z)- and (E)-7-teradecen-1-yl acetate, (Z)- and (E)-7-nonen-1-ol, (Z)- and (E)-9-tetradecen-1-yl acetate, (Z)- and (E)-10-tetradecen-1-yl acetate, (Z)- and (E)-11-tetradecen-1-yl acetate.Pure (Z)-6-nonen-1-ol, which is an attractant of olive fruit fly, D. oleae, and very probably, a constituent of the sex pheromone of females of this insect, has been prepared by a rather efficient copper-catalyzed reaction between (Z)-3-hexen-1-ylmagnesium bromide and oxetane. (9Z,12E)-9,12-Tetradecadien-1-yl acetate, which is the pheromone of Anagasta kuenniella, Ephestia elutella, Cadra figulella, Spodoptera exigua, S. litura, and a component of the sex pheromones of several other Lepidoptera, has been conveniently prepared by using the copper-catalyzed coupling reaction between (E)-1-chloro-2-butene and 10-tetrahydropyranyloxy-1-decenylmagnesium bromide, followed by acetylation and Z-stereoselective reduction of the derived 1,4-enyne.All syntheses have been conducted on a scale to yield less than 50 mmol of the pure sex pheromone components, but seem adaptable for much larger quantities.
- Rossi, Renzo,Carpita, Adriano,Gaudenzi, Loretta,Quirici, Maria Grazia
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p. 237 - 246
(2007/10/02)
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- SYNTHESIS OF HIGHER ACETYLENIC ALCOHOLS
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The alkylation of 1-alkynes in various solvents was investigated, and the optimum conditions for the production of acetylenic alcohols were obtained.
- Kovalev, B. G.,Matveeva, E. D.,Stan, V. V.,Vovk, G. A.,Yudin, L. G.,Kost, A. N.
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p. 1728 - 1733
(2007/10/02)
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