10424-93-8

Usage

Synthesis Reference(s)

Synthesis, p. 529, 1984 DOI: 10.1055/s-1984-30893

InChI:InChI=1/C8H16N2/c1-10(2)9-8-6-4-3-5-7-8/h3-7H2,1-2H3

Upstream product

• 108-94-1 cyclohexanone 
• 1741-01-1 Trimethylhydrazin 
• 57-14-7 N,N-Dimethylhydrazine 

Downstream Products

• 65457-37-6 syn-2-Methylcyclohexanondimethylhydrazon 
• 85292-76-8 (E)-5-(2-Oxo-cyclohexyl)-pent-3-enoic acid 
• 137919-62-1 (E/Z)-2-(2,2-dimethylpropanoyl)cyclohexanone dimethylhydrazone 
• 83314-19-6 (S)-[(S)-2-(Dimethyl-hydrazono)-cyclohexyl]-phenyl-methanol 
• 83314-19-6 (R)-[(S)-2-(Dimethyl-hydrazono)-cyclohexyl]-phenyl-methanol 
• 1126-19-8 2-(3'-chloropropyl)cyclohexanone 
• 59386-47-9 2-decylcyclohexanone 
• 184366-55-0 2-(3-(benzyloxy)propyl)cyclohexanone 
• 181300-46-9 2-(4-benzyloxybutyl)cyclohexanone 
• 54812-97-4 2-(pent-3-yn-1-yl)cyclohexan-1-one 
• 39178-69-3 rac-3-butylcyclohexanone 

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Studies Targeting Ryanodol Result in an Annulation Reaction for the Synthesis of a Variety of Fused Carbocycles

An annulation reaction is described to access a range of polycyclic and highly oxygenated carbocycles. First developed in an approach to the synthesis of ryanodol, metallacycle-mediated annulative diketone-alkyne coupling defines a framework for realization of new retrosynthetic relationships for complex molecule synthesis. In addition to demonstrating this reaction in the context of forging distinct carbocyclic systems, including those featuring a seven-membered ring, the choice of quenching reagent leads to unique reaction outcomes.

Mechanistic study of samarium diiodide-HMPA initiated 5-exo-trig ketyl-olefin coupling: The role of HMPA in post-electron transfer steps

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Mechanistic Study and Development of Catalytic Reactions of Sm(II)

Samarium diiodide (SmI2) is one of the most widely used single-electron reductants available to organic chemists because it is effective in reducing and coupling a wide range of functional groups. Despite the broad utility and application of SmI2 in synthesis, the reagent is used in stoichiometric amounts and has a high molecular weight, resulting in a large amount of material being used for reactions requiring one or more equivalents of electrons. Although few approaches to develop catalytic reactions have been designed, they are not widely used or require specialized conditions. As a consequence, general solutions to develop catalytic reactions of Sm(II) remain elusive. Herein, we report mechanistic studies on catalytic reactions of Sm(II) employing a terminal magnesium reductant and trimethylsilyl chloride in concert with a noncoordinating proton donor source. Reactions using this approach permitted reductions with as little as 1 mol % Sm. Mechanistic studies provide strong evidence that during the reaction, SmI2 transforms into SmCl2, therefore broadening the scope of accessible reactions. Furthermore, this mechanistic approach enabled catalysis employing HMPA as a ligand, facilitating the development of catalytic Sm(II) 5-exo-trig ketyl olefin cyclization reactions. The initial work described herein will enable further development of both useful and user-friendly catalytic reactions, a long-standing, but elusive goal in Sm(II) chemistry.

(Poly)cationic λ3-Iodane-Mediated Oxidative Ring Expansion of Secondary Alcohols

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The present invention provides 4H,6H-5-oxa-2,3,10b-triaza-benzo[e]azulenes, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments. The active compounds of the present invention are useful as therapeutics acting peripherally and centrally in the conditions of dysmenorrhea, male or female sexual dysfunction, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, and aggressive behavior.

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