769-32-4

Basic information

• Product Name: 3,4,5,6,7,8-hexahydroazulen-1(2H)-one
• Synonyms: 3,4,5,6,7,8-hexahydroazulen-1(2H)-one;1,2,3,4,5,6,7,8-Octahydroazulene-1-one
• CAS NO: 769-32-4
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.21756
• EINECS: 212-208-0
• Mol File: 769-32-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 272.2°C at 760 mmHg
• Flash Point: 105.6°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 0.00617mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: 3,4,5,6,7,8-hexahydroazulen-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6,7,8-hexahydroazulen-1(2H)-one(769-32-4)
• EPA Substance Registry System: 3,4,5,6,7,8-hexahydroazulen-1(2H)-one(769-32-4)

Safety Data

• Hazardous Substances Data: 769-32-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 771, 1978 DOI: 10.1016/S0040-4039(01)85392-2

InChI:InChI=1/C10H14O/c11-10-7-6-8-4-2-1-3-5-9(8)10/h1-7H2

Upstream product

• 7125-60-2 1(7)-bicyclo<5.3.0>decene 
• 91897-89-1 1-(cyclohepten-1-yl)-2-propen-1-one 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 61892-24-8 1-trimethylsilylcycloheptene 
• 814-68-6 acryloyl chloride 
• 67250-73-1 1-(1,1-Dichloro-allyl)-cycloheptanol 
• 54133-13-0 (6E,13E)-1,4-Dioxa-spiro[4.9]tetradeca-6,13-diene 
• 214329-86-9 1-nitrobicyclo[5.3.1]undecane-8,11-dione 
• 201230-82-2 carbon monoxide 
• 85236-14-2 1-bromo-2-vinyl cyclohept-1-ene 
• 1030023-35-8 cyclodecane-1,4-dione 
• 628-92-2 Cycloheptene 

Downstream Products

• 93600-81-8 8-Mesitylbicyclo<5.3.0>deca-1(7),8-dien 
• 105543-61-1 2,3,5,6,7,8-hexahydro-1H,4H-azulen-1-one cyclic (1S,2S)-1,2-bis-<(benzyloxy)methyl>ethylene acetal 
• 117583-55-8 2,3,5,6,7,8-hexahydro-1H,4H-azulen-1-one (S,S)-hydrobenzoin ketal 
• 7125-60-2 1(7)-bicyclo<5.3.0>decene 
• 275-51-4 azulene 
• 7206-60-2 1-Phenylazulene 
• 117583-56-9 (3aS,8aR)-2,3,5,6,7,8-hexahydro-3a,8a-methano-1H,4H-azulen-1-one (S,S)-hydrobenzoin ketal 
• 105543-62-2 C₂₉H₃₆O₄ 
• 105543-62-2 (3aS,8aR)-2,3,5,6,7,8-hexahydro-3a,8a-methano-1H,4H-azulen-1-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 93564-03-5 1-Mesitylazulen 
• 58634-37-0 1,4-Pentamethylen-Dewar-Benzol 

Relevant articles and documents

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Palladium-catalyzed intramolecular 5-endo-trig oxidative Heck cyclization: a facile pathway for the synthesis of some sesquiterpene precursors

An efficient and convenient method for the construction of substituted cyclopentenones via palladium-catalyzed intramolecular 5-endo-trig oxidative cyclization has been introduced as a powerful new strategy for the synthesis of sesquiterpenes.

A Novel NO2/OH Exchange in α-Nitro Ketones: A Mechanistic Investigation

The reaction of α-nitro ketones to the corresponding α-hydroxy ketones under basic aqueous conditions, a novel transformation, was studied. The investigation revealed that the reaction is only possible with α-nitro ketones that are CH-acidic in the α′-position and readily deprotonated under the reaction conditions. The NO2/OH exchange was established to proceed with retention of configuration at the stereogenic center, and labeling experiments have shown that the OH O-atom originates, to a great extent, from the solvent. In particular, the stereochemical course of the reaction and the incorporation of external nucleophiles led us to propose a mechanism that involves neighboring-group participation. The product formation is explained by a double SN2 reaction, which proceeds via a favorsii-like cyclopropanone intermediate.