90676-52-1

Upstream product

• 54173-32-9 2-(1-chloro-pentyl)-tetrahydro-furan 
• 110-87-2 3,4-dihydro-2H-pyran 
• 109-72-8 n-butyllithium 
• 49826-98-4 Non-4-yn-1-ol 
• 52054-82-7 6-n-butyl-3,4-dihydro-2H-pyran 
• 101971-66-8 2-butyl-3,3-dichlorotetrahydropyran 
• 693-03-8 n-butyl magnesium bromide 
• 72081-15-3 6-lithio-3,4-dihydro-2H-pyran 
• 50-00-0 formaldehyd 
• 86950-97-2 C₈H₁₅BrMg 
• 110-62-3 pentanal 
• 87436-78-0 (4-hydroxybutyl)-triphenylphosphonium bromide 
• 37423-42-0 non-4-enal 
• 80816-20-2 l-butyl-2-propenyl-vinyl ether 

Downstream Products

• 86252-74-6 (2E,13Z)-octadeca-2,13-dienyl acetate 

Relevant academic research and scientific papers

Modified Ozonolytic Synthesis of 4Z-Nonen-1-ol, an Intermediate for the Synthesis of Sex Pheromones of Cotton Bollworm and Cabbage Moth, from the Cyclic Butadiene-Isoprene Codimer

An improved procedure for preparing 4Z-nonen-1-ol, a key intermediate in the synthesis of sex pheromones of cabbage moth and cotton bollworm, from the cyclic butadiene-isoprene dimer (1-methyl-1Z,5Z-cyclooctadiene) was developed. In this procedure, the peroxide product of regioselective partial ozonolysis (0.9 equiv of O3) of the codimer across the trisubstituted double bond is converted in one step to 9-hydroxy-5Z-nonen-2-one with NaBH(OAc)3, the reagent that does not affect the keto groups present in the structure or formed in the process.

Access to Saturated Thiocyano-Containing Azaheterocycles via Selenide-Catalyzed Regio-A nd Stereoselective Thiocyanoaminocyclization of Alkenes

An efficient route for the synthesis of saturated thiocyano-containing azaheterocycles by selenide-catalyzed regio-A nd stereoselective thiocyanoaminocyclization of alkenes is disclosed. The desired products were obtained in moderate to high yields under mild conditions. The generality of this method was elucidated by its efficient application in thiocyano oxycyclization of alkenes.

Diaminodiphosphine tetradentate ligand and ruthenium complex thereof, and preparation methods and applications of ligand and complex

The invention discloses a diaminodiphosphine tetradentate ligand and a ruthenium complex thereof, and preparation methods and applications of the ligand and the complex, and provides a ruthenium complex represented by a formula I, wherein L is a diaminodiphosphine tetradentate ligand represented by a formula II, and X and Y are respectively and independently chlorine ion, bromine ion, iodine ion,hydrogen negative ion or BH4. According to the present invention, the ruthenium complex exhibits excellent catalytic activity in the catalytic hydrogenation reactions of ester compounds, has high yield and high chemical selectivity, is compatible with conjugated and non-conjugated carbon-carbon double bond, carbon-carbon triple bond, epoxy, halogen, carbonyl and other functional groups, and hasgreat application prospects.

Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates

Ligand-enabled aza-Heck cyclizations and cascades of N-(pentafluorobenzoyloxy)carbamates are described. These studies encompass the first examples of efficient non-biased 6-exo aza-Heck cyclizations. The methodology provides direct and flexible access to carbamate protected pyrrolidines and piperidines.

A facile access to bridged 1,2,4-trioxanes

Bicyclo[3.2.1] type 1,2,4-trioxanes are readily synthesized from precursors that may form intramolecular hemiketals using UHP (H2O2-urea complex) as the source of the peroxy bond and p-TsOH or CSA as the catalyst. The ring closure through an intramolecular Michael addition occurred in a highly stereoselective way, giving only one diasteromer as shown by the NMR spectra.

1,2-Silyl-migrative cyclization of vinylsilanes bearing a hydroxy group: Stereoselective synthesis of multisubstituted tetrahydropyrans and tetrahydrofurans

Acid-catalyzed intramolecular addition of a hydroxy group to α-alkylated vinylsilanes has been studied. Treatment of (Z)-5-alkyl-5-silyl-4-penten-1-ols 1 (R = alkyl) with 5 mol % TiCl4 in CHCl3 gave trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis = > 99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the C-C double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis-selectivity. In the cyclization of (Z)-1 (R = Bu), the silyl group used, the reaction time, and the yield of 2 were as follows: SiMe2Ph, 9.5 h, 75%; SiMe3, 7.5 h, 66%; SiMePh2, 24 h, 58%; SiMe2-t-Bu, 0.75 h, 85%; SiMe2Bn, 1.5 h, 78%. This 1,2-silyl-migrative cyclization could be applied to stereoselective synthesis of trisubstituted tetrahydropyrans. The acid-catalyzed reaction of 1-, 2-, or 3-substituted (Z)-5-silyl-4-nonen-1-ols 8 gave r-2,t-3,c-6-, r-2,t-3,t-5-, or r-2,t-3,c-4-trisubstituted tetrahydropyrans with high diastereo-selectivity, respectively. (Z)-4-Alkyl-4-silyl-3-buten-1-ols 5 as well as 1 underwent the 1,2-silylmigrative cyclization to give 2-alkyl-3-silyltetrahydrofurans 6 with high trans-selectivity. This silicon-directed cyclization was also available for the stereoselective synthesis of tri- and tetrasubstituted tetrahydrofurans.

Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group. Benzyldimethylsilyl group as an effective promoter and novel hydroxy surrogate

A benzyldimethylsilyl (BnDMS) group was found to effectively enhance the reactivity of vinylsilanes toward the acid-catalyzed intramolecular addition of a hydroxy group in comparison with a dimethylphenylsilyl group. The BnDMS group of the resultant cyclized products could be easily converted to a hydroxy group by the action of TBAF-H2O2-KHCO3. (C) 2000 Elsevier Science Ltd.

Synergistic sex pheromone components of white-spotted tussock moth, Orgyia thyellina

In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic-electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6-11-one) and (Z)-6-heneicosen-9- one, the latter termed here 'thyellinone.' In field experiments in Japan, Z6- 11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997-1998 summer, 45,000 commercial trap lures baited with 2000 μg of Z6-11-one and 100 μg of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.

A convergent and highly efficient synthesis of (E,Z)-2,13-octadecadienyl acetate and (E,Z)-3,13-octadecadienyl acetate, components of the sex pheromone of the Leopard Moth Zeuzera pyrina, through sulfones

(equation presented) A new, convergent synthesis of (E,Z)-2,13-octadecadienyl acetate (1) and (E,Z)-3,13-octadecadienyl acetate (2), the two key components of the leopard moth Zeuzera pyrina, from 2-chloromethyltetrahydrofuran in good overall yields and stereomeric purity is reported. The synthesis of both components utilizes the common intermediate sulfone 12 as a convenient building block to be coupled with iodoacetylenic derivatives 9 or 17 in the key step.