10424-93-8

Basic information

• Product Name: Cyclohexanone dimethyl hydrazone
• Synonyms: Cyclohexanone dimethyl hydrazone
• CAS NO: 10424-93-8
• Molecular Formula: C₈H₁₆N₂
• Molecular Weight: 140.226
• Mol File: 10424-93-8.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 203.7°Cat760mmHg
• Flash Point: 77°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 0.274mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: Cyclohexanone dimethyl hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone dimethyl hydrazone(10424-93-8)
• EPA Substance Registry System: Cyclohexanone dimethyl hydrazone(10424-93-8)

Safety Data

• Hazardous Substances Data: 10424-93-8(Hazardous Substances Data)

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

Downstream Products

• 157372-80-0 N'-[2-Allyl-cyclohex-(Z)-ylidene]-N,N-dimethyl-hydrazine 
• 82026-21-9 2-(4,5-hexadienyl)-1-cyclohexanone 
• 771574-37-9 2-(5,6-heptadienyl)-1-cyclohexanone 
• 58706-84-6 [2-(Dimethyl-hydrazono)-cyclohexyl]-diphenyl-methanol 
• 1004-77-9 2-isopropylcyclohexanone 
• 10488-25-2 cis-2-isopropylcyclohexan-1-ol 

Relevant articles and documents

Synthesis of Lactones by Baeyer-Villiger Oxidation with Magnesium Monoperphthalate Hexahydrate

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

The mechanistic importance of HMPA and proton donors (methanol, 2-methyl-2-propanol, and 2,2,2-trifluoroethanol) on SmI2-initiated 5-exo-trig ketyl-olefin cyclizations has been examined using stopped-flow spectrophotometric studies. In the pres

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.

Synthesis of Highly Oxygenated Carbocycles by Stereoselective Coupling of Alkynes to 1,3- and 1,4-Dicarbonyl Systems

Densely substituted and highly oxygenated carbocycles are challenging targets for synthesis. In particular, those possessing numerous contiguous, fully substituted carbon atoms (i.e., tertiary alcohols and quaternary centers) are often not accessible in a direct fashion, necessitating the strategic decoupling of ring-formation from the establishment of functionality about the system. Here, we describe an approach to the construction of highly oxygenated mono-, di-, and polycyclic carbocycles from the reaction of disubstituted alkynes with β- or γ-dicarbonyl systems. These processes embrace a variant of metallacycle-mediated annulation chemistry where initial alkyne-carbonyl coupling is followed by a second, now intramolecular, stereoselective C-C bond-forming event. In addition to revealing the basic reactivity pattern in intermolecular settings, we demonstrate that this class of reactivity is quite powerful in a fully intramolecular context and, when terminated by a stereoselective oxidation process, can be used to generate polycyclic systems containing a fully substituted and highly oxygenated five-membered ring.