83670-89-7

Basic information

• Product Name: 1-Heptanone, 3-hydroxy-1-phenyl-
• CAS NO: 83670-89-7
• Molecular Formula: C13H18O2
• Molecular Weight: 206.285
• Mol File: 83670-89-7.mol

Chemical Properties

• CAS DataBase Reference: 1-Heptanone, 3-hydroxy-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Heptanone, 3-hydroxy-1-phenyl-(83670-89-7)
• EPA Substance Registry System: 1-Heptanone, 3-hydroxy-1-phenyl-(83670-89-7)

Safety Data

• Hazardous Substances Data: 83670-89-7(Hazardous Substances Data)

Upstream product

• 1017-09-0 5-n-butyl-3-phenyl-Δ²-isoxazoline 
• 144741-39-9 1-Phenyl-3-trimethylsilanyloxy-heptan-1-one 
• 110-62-3 pentanal 
• 70-11-1 α-bromoacetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 4636-16-2 iodoacetophenone 
• 592-41-6 1-hexene 
• 698-16-8 benzohydroximoyl chloride 
• 64235-53-6 (E)-1-phenyl-2-hepten-1-one 

Relevant articles and documents

Reductive ring cleavage of nonconjugated Δ2-isoxazolines to β-hydroxy ketones with aluminum and copper(II) chloride

A facile, economic, and efficient protocol for the reduction of nonconjugated Δ2-isoxazolines to the corresponding β-hydroxy ketones using Al/CuCl2 as the reducing agent has been developed. The method is both rapid and complete requiring less than ten minutes to attain total ring cleavage. This is the first example of using an in situ prepared Al/Cu couple in organic synthesis. Georg Thieme Verlag Stuttgart · New York.

Visible-light-induced photoreductive generation of radicals from epoxides and aziridines

It's a trap! Both epoxides and aziridines substituted by an aryl ketone can be reduced efficiently using visible-light photoredox catalysts. The radicals generated were trapped by allyl sulfones, and formed α-branched β-hydroxy or amino derivatives with high diastereocontrol (see scheme; dtbbpy=4,4′-di-tert-butyl-2,2′-bipyridine, ppy=2-phenylpyridine). Copyright

Intermolecular aldol type reactions of phenacyl bromide with aldehydes mediated by active metallic indium in aqueous media

Mediated by active metallic indium generated in situ from metallic samarium and InCl3.4H2O, phenacyl bromide and aldehydes smoothly underwent intermolecular aldol type reaction in aqueous media affording β-hydroxy ketones in good yie

Reformatsky-type reaction of α-haloketones promoted by titanium tetraiodide

Titanium(IV) tetraiodide induces a Reformatsky-type reaction of α-iodoketones with carbonyl compounds to give β-hydroxy ketones in good to high yields.

On indium(III) chloride-catalyzed aldol reactions of silyl enol ethers with aldehydes in water

Contrary to previous reports, it was found that hydrolysis of silyl enol ethers is superior to the desired condensation in InCl3-catalyzed aldol reactions of silyl enol ethers with aldehydes in water. The reactions were found to proceed in certain amounts in the presence of a catalytic amount of a Lewis acid under neat (solvent-free) conditions, while substrate limitation was observed in these reactions. Use of InCl3 as a Lewis acid in aldol reactions in micellar systems is also reported.

Indium-trichloride catalyzed Mukaiyama-aldol reaction in water: Solubility, aggregation and internal pressure effect

Studies on the effects of water and the binding characteristic of InCl3, in the Mukaiyama-aldol reaction with an in depth mechanistic probe on the probable internal pressure and aggregation effects exerted in this media.

Study on the "tin-ene" reaction of α-bromoacetophenone and metallic tin with aldehydes

β-hydroxy ketones were obtained in good yields by the "tin-ene" reactions of α-bromoacetophenone and metallic tin with aldehydes.

Homogeneous catalysis. Transition metal based lewis acid catalysts

Transition metal based Lewis acids provide catalysts for the Diels-Alder and Mukaiyama reactions. These catalysts must possess an electron deficient axophilic metal center and a labile coordination position. Unlike traditional Lewis acids, those derived from transition metals can function in the presence of water and have well defined structures. It is shown how a normally electron rich ruthenium atom can be converted to a Lewis acid by incorporation of electron withdrawing ligands and ligands with hard donor atoms. This ruthenium complex, [Ru(salen)(NO)(H2O)]+, is an efficient catalyst for the Diels-Alder reaction, but in the Mukaiyama reaction, it tends to be reduced and thereby deactivated by the silyl enol ether. It is shown that the complex [TiCp*2(H2O)2]2+ (Cp* is pentamethylcyclopentadienyl) is an efficient catalyst for the Diels-Alder reaction even when water is present. Similarly, the triflato complexes [TiCp2(CF3 SO3)2] and [ZrCp2(CF3SO3)2] (Cp is cyclopentadienyl) are efficient catalysts for both the Diels-Alder and Mukaiyama reactions. All of these catalysts are effective at very low loadings of ≈ 1 mol%. Catalysis has been shown to occur via substrate-catalyst adducts and moreover these adducts are formed rapidly and reversibly as required for efficient catalysis.

REDUCTION OF DELTA 2-ISOXAZOLINES. PART 3: RANEY-NICKEL CATALYZED FORMATION OF beta -HYDROXY KETONES.

The importance of the beta -hydroxy ketone moiety has led to the development of a wide variety of aldol type methodologies for its construction. A conceptually new approach to these 'aldol adducts' is presented on the basis of left bracket 3 plus 2 right bracket dipolar cycloaddition of in situ generated nitrile oxides and olefins followed by reduction of the resulting DELTA **2-isoxazolines. This approach provides a nice complement of the aldol type reaction. Optimum conditions for the transformation of DELTA **2-isoxazolines to beta -hydroxy ketones use Raney-nickel catalyst, boric acid, 5/1 MeOH/H//2O, and hydrogen gas. Under these mild conditions, 3-methyl-5-n-butyl- DELTA **2-isoxazoline is transformed to 4-hydroxy-2-octanone in high yield. Thus 'directed aldol' type adducts are readily available by selection of the appropriate olefin and nitrile oxide precursor (usually the 1 degree nitro compound).