Reaction of Magnesium Alkylidene Carbenoids with Lithium α-Sulfonyl Carbanions: A Novel Synthesis of Tri- and Tetra-substituted Allenes from 1-Chlorovinyl p-Tolyl Sulfoxides and Sulfones

スポンサーリンク

概要

• 論文の詳細を見る

• Treatment of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from ketones and chloromethyl p-tolyl sulfoxide, with ethylmagnesium chloride or isopropylmagnesium chloride at below - 78℃ gave magnesium alkylidene carbenoids in about 90% yields. The reaction of the generated carbenoids with lithium α-sulfonyl carbanions was found to afford tri- and tetra-substituted allenes. Both cyclic ketones and acyclic ketones were useful in this procedure. However, the 1-chlorovinyl p-tolyl sulfoxides derived from aldehydes gave only rearranged products, acetylenes, under the reaction conditions. The magnesium alkylidene carbenoid derived from an optically active 1-chlorovinyl p-tolyl sulfoxide was treated with lithium α-carbanion of 1-naphthyl phenyl sulfone; however, the obtained allene was found to be racemic. The mechanism of this reaction is also discussed.

• 公益社団法人日本薬学会の論文
• 2003-08-01

著者

• TAKANO Koji

  Department of Nephrology and Endocrinology, Faculty of Medicine, University of Tokyo

• Satoh Tsuyoshi

  Department Of Chemistry Faculty Of Science Tokyo University Of Science

• Takano Koji

  Department Of Nephrology And Endocrinology University Of Tokyo Faculty Of Medicine

• Takano K

  Department Of Chemistry Faculty Of Science Tokyo University Of Science

• Satoh Tsuyoshi

  Department Of Agricultural Chemistry Obihiro University Of Agriculture And Veterinary Medicine

• Sakamoto Tatsuya

  Department of Chemistry, Faculty of Science, Tokyo University of Science

• Watanabe Masanori

  Department of Chemistry, Faculty of Science, Tokyo University of Science

• Watanabe Mitsuo

  School Of Pharmaceutical Sciences Teikyo Univ.

• Watanabe M

  School Of Pharmaceutical Sciences Teikyo Univ.

• Watamabe Minae

  Faculty Of Pharmaceutical Sciences Setsunan University

• Sakamoto Tatsuya

  Department Of Chemistry Faculty Of Science Tokyo University Of Science

• Takano Koji

  Department Of Chemistry Faculty Of Science Tokyo University Of Science

• Watanabe Masanori

  Department Of Analytical Chemistry Faculty Of Engineering Yokohama National University

関連論文

• A Kindred of Familial Acromegaly without Evidence for Linkage to MEN-1 Locus
• A New Synthesis of 2-Sulfanyl Allylic Alcohols and α-Sulfanyl Ketones from Carbonyl Compounds and 1-Chloroalkyl p-Tolyl Sulfoxides with Carbon-Carbon Bond-Formation
• Selective Oxidation of Alcohols at the Benzylic Position by Benzeneseleninic Anhydride
• Dianion of Sulfinylacetone as a Synthetic Equivalent of β-Enolate of Propionic Acid: A Novel Synthesis of Carboxylic Acids from Alkyl Halides with Three-Carbon Elongation
• Reaction of Magnesium Alkylidene Carbenoids with Lithium α-Sulfonyl Carbanions: A Novel Synthesis of Tri- and Tetra-substituted Allenes from 1-Chlorovinyl p-Tolyl Sulfoxides and Sulfones
• Rapid and Frequent Somatic Embryogenesis from Single Cells of Regenerated Carrot Plantlets
• A Japanese Patient with Lipoprotein Lipase Deficiency Homozygous for the Gly188Glu Mutation Prevalent Worldwide
• VISUALIZING EXOCYTOSIS IN RAT ANTERIOR PITUITARY CELL CLUSTER USING TWO-PHOTON EXTRACELLULAR POLARY TRACER (TEP) METHOD
• Mechanism of D_2 Agonist-induced Inhibition of GH Secretion from Human GH-secreting Adenoma Cells
• Mechanism of Adrenomedullin-induced Prolactin Release from Human Prolactin-releasing Adenoma Cells
• Mechanisms of TRH-induced GH Release (Paradoxical Response) in Human Somatotroph Adenoma Cells
• Spontaneous Recovery from Hypopituitarism in a Man with Lymphocytic Hypophysitis: A Case Report
• The Conventional Transport Properties of Primary Solid Solutions. : I. Indium Rich Alloys.
• Analyses of Factors Influencing the Acute Effect of Octreotide in Growth Hormone-secreting Adenomas
• IA-25 Studies on regulated secretion pathway in GH3 stable cell line expressing EYFP-GH fusion protein(THE 46TH ANNUAL MEETING OF THE JAPAN SOCIETY OF HISTOCHEMISTRY AND CYTOCHEMISTRY)
• Resin Glycosides. XXIII. Two Novel Acylated Trisaccharides Related to Resin Glycoside from the Seeds of Cuscuta chinensis
• The First Example of α-Thiomagnesiums Generated from Dithioacetal Monoxides with Grignard Reagent; Their Properties and Some Synthetic Applications
• Absolute Structure of Panaxytriol
• Flocculating Property of Extracellular Polymeric Substance Derived from a Marine Photosynthetic Bacterium, Rhodovulum sp.
• Treatment of Aquarium Water by Denitrifying Photosynthetic Bacteria Using Immobilized Polyvinyl Alcohol Beads
• Synthesis of Panax Acetylenes : Chiral Syntheses of Acetylpanaxydol, PQ-3 and Panaxydiol
• The Effect of Impurity Scattering on the Hall Coefficient of the Polyvalent Metal Alloys
• Galvanomagnetic Size Effects in Indium
• Epidemiological study of gastroenteropancreatic neuroendocrine tumors in Japan
• Purification and Properties of an Enzyme Oxidizing Nitrite to Nitrate from Candida rugosa(Microbiology & Fermentation Industry)
• Fructosamine Assay Using Albumin Extracted from Serum
• Generation of Superoxide Anions during the Reaction of Guanidino Compounds with Mehylglyoxal
• Chemiluminescence-HPLC for the Assay of Guanidino Compounds
• Automatic System for the Assay of Guanidino Compounds to Assess Uremic Status
• Sulfoacylated Macro-Porous Polystyrene-Divinylbenzene Low-Capacity Cation Exchanger Selective for Amino Acids
• Preventive Effects of Nitroglycerin Buccal Tablets to Increase of Blood Pressure during Dental Treatment
• The Generation of Lucigenin Chemiluminescence from the Reaction of Guanidino Compounds with Phenylglyoxal under Alkaline Conditions and Its Application
• Electronic Structure of Alkali Metals. I. : Fermi Surfaces of Sodium and Potassium
• Phosphorylation of D-Glucose Derivatives with Inorganic Cyclo-Triphosphate : Substituent Effect at the 5-CH_2OH or 2-OH Group
• Selective Synthesis of β-D-Glucopyranosyl 1-Triphosphate by Reaction of D-Glucopyranose with Inorganic cyclo-Triphosphate
• Histopathological Changes of Joint Capsule after Joint Immobility Compared with Aging in Rats
• Ultrastructural study of upper surface layer in rat articular cartilage by "in vivo cryotechnique" combined with various treatments
• Functional molecular morphology of anterior pituitary cells, from hormone production to intracellular transport and secretion
• The Ordinary Transport Properties of Lead Alloys
• Interpretation of the Hall Coefficient and the Resistivity of Noble Metal Alloys
• Hall Coefficients of Beta-Phase Alloys
• Fermentative L-(+)-lactic acid production from non-sterilized rice washing drainage containing rice bran by a newly isolated lactic acid bacteria without any additions of nutrients(BIOCHEMICAL ENGINEERING)
• Stability of $\alpha$ and $\beta$ Phases of Noble Metal Alloys
• Histopathological Changes in Joint Components in a Rat Knee Joint Contracture Model Following Mobilization
• Urinary growth hormone level and insulin-like growth factor-1 standard deviation score (IGF-SDS) can discriminate adult patients with severe growth hormone deficiency
• Fermentative L-(+)-lactic acid production from non-sterilized rice washing drainage containing rice bran by a newly isolated lactic acid bacteria without any additions of nutrients

もっと見る 閉じる

スポンサーリンク