Oxidation of 2,4-alkadienoic esters with selenium dioxide. A new synthesis of furans and selenophenes.
スポンサーリンク
概要
- 論文の詳細を見る
Direct oxidation of 2,4-alkadienoic esters with selenium dioxide gave 5-alkyl-2-furancarboxylic esters along with 5-alkyl-2-selenophenecarboxylic esters. Ethyl 5-methylfurancarboxylate was converted to 5-hydroxymethyl-2-furancarbaldehyde, a component of honey, via ethyl 5-bromomethyl-2-furancarboxylate (<B>5</B>) in good yield. The compound <B>5</B> was converted to (5-ethoxycarbonyl-2-furyl)methyl dimethyldithiocarbamate possessing fungicidal activity. Reaction of triphenylphosphonium salt of <B>5</B> with nonanal gave ethyl 5-(1-decenyl)-2-furancarboxylate (E/Z=88:12) in 86% yield. Ethyl 5-methyl-2-selenophenecarboxylate was also converted to ethyl 5-(1-decenyl)-2-selenophenecarboxylate (E/Z=7:3) in 30% total yield.
- 公益社団法人 日本化学会の論文
著者
-
Tsuboi Sadao
Department Of Applied Chemistry Faculty Of Engineering Okayama University
-
Ono Shin-ichiro
Department of Synthetic Chemistry, School of Engineering, Okayama University
-
Takeda Akira
Department Of Gastroenterology Osaka General Medical Center
-
Ono Shin-ichiro
Department Of Synthetic Chemistry School Of Engineering Okayama University
-
Watanabe Kenji
Department Of Agricultural Chemistry College Of Agriculture And Veterinary Medicine Nihon University
-
Mimura Shigetoshi
Department of Synthetic Chemistry, School of Engineering, Okayama University
-
Watanabe Kenji
Department of Synthetic Chemistry, School of Engineering, Okayama University
-
Takeda Akira
Department of Applied Chemistry, Faculty of Engineering, Okayama University
関連論文
- Fractionation of metal complexes with dissolved organic matter in a rhizosphere soil solution of a humus-rich Andosol using size exclusion chromatography with inductively coupled plasma-mass spectrometry(Soil Chemistry and Soil Mineralogy)
- A Case of Vertebral Artery Dissection Associated with Morning Blood Pressure Surge
- An Herbal Medicine Orengedokuto Prevents Indomethacin-Induced Enteropathy(Pharmacology)
- Roles of double-balloon endoscopy in the diagnosis and treatment of Crohn's disease : a multicenter experience
- ADVANTAGES OF TRIPLE THERAPY WITH MIZORIBINE, CYCLOSPORINE AND PREDNISOLONE OVER OTHER TYPES OF TRIPLE AND/OR DOUBLE THERAPY INCLUDING CYCLOSPORINE FOR RENAL TRANSPLANTATION
- HRP intracellular staining using the monitored pressure injection combined with PAP immunohistochemistry
- Reduction of 15-hydroxyprostaglandin dehydrogenase expression is an independent predictor of poor survival associated with enhanced cell proliferation in gastric adenocarcinoma
- Prevalence of mid-gastrointestinal bleeding in patients with acute overt gastrointestinal bleeding : multi-center experience with 1,044 consecutive patients
- A prospective, single-blind trial comparing wireless capsule endoscopy and double-balloon enteroscopy in patients with obscure gastrointestinal bleeding
- Phenotypic change and accumulation of smooth muscle cells in strictures in Crohn's disease : relevance to local angiotensin II system
- Transient activation of LHRH neuron system of the Japanese quail by photic stimuli of long days
- Wireless capsule endoscopy in pediatric patients : the first series from Japan
- Cloning and Heterologous Expression of a β-Fructofuranosidase Gene from Arthrobacter globiformis IFO 3062, and Site-Directed Mutagenesis of the Essential Aspartic Acid and Glutamic Acid of the Active Site (ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHN
- Cloning and Heterologous Expression of a Glucodextranase Gene from Arthrobacter globiformis I42, and Experimental Evidence for the Catalytic Diad of the Recombinant Enzyme(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)
- Differences in Protein Structure and Similarities in Catalytic Function of Two L-Stereoselective Carbonyl Reductases from Bakers' Yeast
- DIFFERENT ONTOGENESIS OF α-ENDORPHIN POSITIVE CELLS IN THE ANTERIOR AND THE INTERMEDIATE LOBES OF RAT HYPOPHYSIS
- Correlative Ontogenic Development of Catecholaminergic Terminals and LHRH Terminals in the Rat Median Eminence
- ANTIFUNGAL ISOFLAVONE LUTEONE AND ITS METHYL ETHERS
- An Isozyme of Earthworm Serine Proteases Acts on Hydrolysis of Triacylglycerol
- Purification and Characterization of α-Keto Amide Reductase from Saccharomyces cerevisiae
- EXPRESSION OF BRUNO LIKE GENE IN STEM CELLS OF THE PLANARIAN DUGESIA JAPONICA(Developmental Biology,Abstracts of papers presented at the 74^ Annual Meeting of the Zoological Society of Japan)
- Planarian Cytochrome b_ : Conservation of a Six Transmembrane Structure and Localization along the Central and Peripheral Nervous System^1
- Macrophomate Synthase: Characterization, Sequence, and Expression in Escherichia coli of the Novel Enzyme Catalyzing Unusual Multistep Transformation of 2-Pyrones to Benzoates^1
- The production of interferon-γ-inducible protein 10 by granulocytes and monocytes is associated with ulcerative colitis disease activity
- Effect of Soybean Saponin on Trypsin-Inhibiting Activity of Bowman-Birk Inhibitor
- THE ROLES OF Xwnt8, FGF, VegT, Xbra IN FORMATION OF POSTERIOR STRUCTURES IN XENOPUS EMBRYOS(Developmental Biology,Abstracts of papers presented at the 74^ Annual Meeting of the Zoological Society of Japan)
- Enzymatic Conversion of Pheophorbide a to the Precursor of Pyropheophorbide a in Leaves of Chenopodium album
- Characterization of intracellular free Ca2+ movements in neural progenitor cells derived from ES cells transfected with MASH 1 transcription factor gene
- PRIMARY MALIGNANT LYMPHOMA OF THE PENIS : A CASE REPORT
- POTENTIAL OF AUTOFLUORESCENCE COLONOSCOPY FOR PATIENTS WITH ULCERATIVE COLITIS
- Crohn's disease complicated by adult-onset Still's disease
- Effects of Additives in the Reduction Using Bakers' Yeast Cell-Free Extract
- A Convenient Synthesis of Platelet-Activating Factors and Their Analogues from Chiral Epichlorohydrin
- Synthesis of 2,2'-Anhydro-1-(3'-deoxy-3'-bromo-β-D-arabinofuranosyl)thymine and Its Derivatives from 5'-O-Trityl-2',3'-thymidinene
- Intracranial Extension of an Orbital Pseudotumor Accompanied by Internal Carotid Artery Occlusion : Case Report
- Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
- Unexpected Course of the Intramolecular Darzens Condensation of Dichloroacetoxybenzaldehyde.A Novel One-step Synthesis of 2, 2-Dichloro-3-(2-hydroxyphenyl)-3-(2-formylphenoxy)propionic Acid
- The importance of laminin 5 in the dermal-epidermal basement membrane
- Ifosfamide encephalopathy associated with chemotherapy for musculoskeletal sarcomas : incidence, severity, and risk factors
- Phosphoenolyruvate Carboxylase of an Ammonia-Oxidizing Chemoautotrophic Bacterium, Nitrosomonas europaea ATCC 25978
- Basic and clinical studies of percutaneous radiofrequency ablation of osteoid osteoma using a standard electrosurgical generator
- Relative and Absolute Configuration of Antitumor Agent SW-163D
- P-528 Biosynthetic Study of Antitumor Antibiotic Echinomycin : Formation of Quinoxaline Ring and Enzymatic Macrocyclization
- PB185 Synthesis of Some Natural Products via the Chiral Reduction of Ketones with Bakers' Yeast
- Identification of asymmetrically localized transcripts along the animal-vegetal axis of the Xenopus egg
- Differential gene expression between the embryonic tail bud and regenerating larval tail in Xenopus laevis
- Hydrogen in Iron : Its Enhanced Dissolution under Pressure and Stabilization of the γ Phase
- PLANARIAN VASA-RELATED GENES EXPRESSED IN THE STEM CELLS(Developmental Biology)(Proceedings of the Seventy-Third Annual Meeting of the Zoological Society of Japan)
- Wound healing in denervated rat skin
- Perturbation of Notch/Suppressor of Hairless pathway disturbs migration of primordial germ cells in Xenopus embryo
- Mixed Duct-Acinar-Islet Cell Tumor of the Pancreas : Report of a Case
- De novo development and self-replenishment of B cells
- Colon Carcinoma After Thymectomy for Myasthenia Gravis : Report of a Case
- Spinal cord is required for proper regeneration of the tail in Xenopus tadpoles
- Cigarette Smoking and its Association with Overlapping Gastroesophageal Reflux Disease, Functional Dyspepsia, or Irritable Bowel Syndrome
- Granulocyte-colony-stimulating-factor-producing hepatocellular carcinoma
- Target biopsy or step biopsy? Optimal surveillance for ulcerative colitis : a Japanese nationwide randomized controlled trial
- Extraskeletal myxoid chondrosarcoma with multiple skeletal metastases
- Role of Th-2 cytokines in the development of Barrett's esophagus in rats
- On the Electromagnetic Interactions in the B and D Mesons and Their Structure : Particles and Fields
- Exploring the Biosynthesis of Natural Products and Their Inherent Suitability for the Rational Design of Desirable Compounds through Genetic Engineering
- Novel Statistical Classification Model of Type 2 Diabetes Mellitus Patients for Tailormade Prevention Using Data Mining Algorithm
- Determination of total contents of bromine, iodine and several trace elements in soil by polarizing energy-dispersive X-ray fluorescence spectrometry(Soil Chemistry and Soil Mineralogy)
- Calorimetric Studies of the Behavior of Hydrogen in Vanadium and Vanadium Alloys
- A comprehensive overview on genomically directed assembly of aromatic polyketides and macrolide lactones using fungal megasynthases
- Synergism Between Interleukin (IL)-17 and Toll-like Receptor 2 and 4 Signals to Induce IL-8 Expression in Cystic Fibrosis Airway Epithelial Cells
- Simple method of detection of the strains of fluorescent Pseudomonas spp. producing antibiotics, pyrrolnitrin and phloroglucinol
- The Usefulness of Double-balloon Enteroscopy in Gastrointestinal Stromal Tumors of the Small Bowel with Obscure Gastrointestinal Bleeding
- Overexpressing transcriptional regulator in Chaetomium globosum activates a silent biosynthetic pathway : evaluation of shanorellin biosynthesis
- The distribution coefficient for cesium in different clay fractions in soils developed from granite and Paleozoic shales in Japan(Soil chemistry and soil mineralogy)
- Clinical Classification of Subgroups According to the Rome III Criteria Cannot be Used to Distinguish the Associated Respective Pathophysiology in Japanese Patients with Functional Dyspepsia
- Precise Endoscopic and Pathologic Features in a Crohn's Disease Case with Two Fistula-associated Small Bowel Adenocarcinomas Complicated by an Anal Canal Adenocarcinoma
- A highly stereoselective synthesis of (E)-enol lactones by the Wittig reaction of cyclic anhydrides with (.ALPHA.-alkoxycarbonyl-ethylidene)triphenylphosphorane.
- Partition of Soybean Saponins between Butanol and Water.
- Analysis of localization and reorganization of germ plasm in Xenopus transgenic line with fluorescence-labeled mitochondria
- Synthesis and 13C NMR spectra of endo-5-(4-imidazolyl)bicyclo[2.2.2]oct-endo- and exo-2-yl trans-cinnamates.
- Asymmetric Reduction of Carbon-Carbon Double Bonds of Conjugated Enones with Fermenting Bakers' Yeast.
- The Reaction of Ethyl Alkylchloropyruvate with Sodiomalonate and Sodioacetoacetate
- Synthesis and hydrolysis of 4-acetoxymethylbenzimidazoles. Effects of freezing an internal rotation on intramolecular catalysis by a benzimidazolyl group.
- A new method for the synthesis of 3,5-disubstituted 2(5H)-furanones. Synthesis of (.+-.)-acarenoic acid.
- Oxidation of 2,4-alkadienoic esters with selenium dioxide. A new synthesis of furans and selenophenes.
- A stereoselective synthesis of (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid), the sex attractant of the black carpet beetle.
- Electrochemical reduction of exo-5-acetyl-endo-6-trichloromethylbicyclo[2.2.1]hept-2-ene.
- Oxidation of alcohols with electrolytic manganese dioxide. Its application for the synthesis of insect pheromones.
- Asymmetric synthesis of (2R,3S)-2,3-epoxyoctanal, a key intermediate of 14,15-leukotriene A4.
- Chemistry of α-Haloaldehyde. VI. Reaction of 2-Chloro-2-methylpropanal with Benzoylacetonitrile in the Presence of Potassium Carbonate
- A new synthesis of pyrocin and related compounds.
- A new synthesis of 4-methoxy-6-valeryl-5,6-dihydro-2-pyrone.
- Diels-AIder Reactions of 5,5,5-Trichloro-3-penten-2-one and Related Compounds
- Synthesis of methyl-substituted 1-cyclopentene-1-carboxylates and related compounds.
- Reaction of Ethyl α,α-Dichloroacetoacetate with Aldehydes
- Electrolyses of 2,2-Dichloro-3-phenylcyclopropanecarboxylic Acids in Hydroxylic Solvents with a Platinum Anode
- A convenient synthesis of 4-(2,2-dichloroethenyl)-5,5-dimethyl-tetrahydro-2-furanone derivatives, a key intermediate of permethrinic acid.
- A Michael addition-induced Favorskii rearrangement.
- Reinvestigation of base-catalyzed condensation of ethyl .ALPHA.,.ALPHA.-dichloroacetoacetate with aldehydes. A new synthesis of (.+-.)-disparlure.
- Synthesis of 5-[(E)-1-alkenyl]-3(2H)-furanones by the stereoselective dehydration with Me3SiCl.
- Chemistry of α-Haloaldehydes. II. Base-catalyzed Condensation of α-Haloaldehydes with Methyl Chloroacetate
- The Base-catalyzed Condensation of α-Haloaldehydes with Dichloroacetates
- Asymmetric reduction of .ALPHA.-(dimethylthiocarbamoylthio) carbonyl compounds with bakers' yeast.
- One-pot C-arylmethylation of active methylene compounds with aromatic aldehydes induced by a Me3SiCl-NaI-MeCN reagent.