134179-01-4

Basic information

• Product Name: 1-Oxaspiro[4.4]nonan-6-one
• Synonyms: 1-Oxaspiro[4.4]nonan-6-one
• CAS NO: 134179-01-4
• Molecular Formula: C8H12O2
• Molecular Weight: 140.17968
• Mol File: 134179-01-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Oxaspiro[4.4]nonan-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Oxaspiro[4.4]nonan-6-one(134179-01-4)
• EPA Substance Registry System: 1-Oxaspiro[4.4]nonan-6-one(134179-01-4)

Safety Data

• Hazardous Substances Data: 134179-01-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Oxaspiro[4.4]nonan-6-one is utilized as a key intermediate in the synthesis of various pharmaceuticals for its unique structure and biological activity. It contributes to the development of new drugs by providing a foundation for chemical modifications and enhancements in drug efficacy and safety.
Used in Fragrance Industry:
In the fragrance industry, 1-Oxaspiro[4.4]nonan-6-one is employed as a component in the creation of unique scents. Its distinctive structure allows for the development of novel fragrances that can be used in a variety of consumer products, such as perfumes, cosmetics, and personal care items.
Used in Organic Synthesis:
1-Oxaspiro[4.4]nonan-6-one serves as a building block in organic synthesis, enabling the construction of a diverse range of organic compounds. Its versatility in forming new chemical entities makes it an essential component in the development of innovative materials and compounds for various applications, including but not limited to, pharmaceuticals, agrochemicals, and specialty chemicals.

Upstream product

• 134179-00-3 1-(4,5-dihydrofuran-2-yl)cyclobutanol 
• 141411-97-4 (S*)-1-oxaspiro<4.4>nonan-6-one 
• 341032-12-0 (3R,5R,6S)-3-Phenyl-1,4,7-trioxa-dispiro[4.0.4.3]tridecan-2-one 
• 341032-60-8 (3R,5S,6S)-3-Phenyl-1,4,7-trioxa-dispiro[4.0.4.3]tridecan-2-one 
• 1374550-54-5 1-(4-hydroxybut-1-yn-1-yl)cyclobutan-1-ol 

Downstream Products

• 341032-13-1 (+)-1-oxaspiro[4.4]nonan-6-one 

Relevant articles and documents

Studies of π-diastereofacial selectivity: Spiro 2-tetrahydrofuran and 2-tetrahydrothiophene ketones

The facial influence and synthetic utility of oxygen, sulfur and carbon atoms adjacent to the ketone in the series of α-spiro ketones 2, 3, and 4 upon nucleophilic addition has been examined. Addition to the carbonyl group displayed a preference for attack anti to the heteroatom in competition with carbon in synthetically useful ratios. Hydride reduction of 2 with chelating reagenst (NaBH4, LiAlH4 etc.) reversed this facial preference.

Gold-catalyzed ring expansions of 1-alkynylcyclobutanol derivatives via tandem hydration and α-ketol rearrangement

We report herein the gold-catalyzed tandem hydration/α-ketol rearrangement of 1-alkynylcyclobutanol derivatives, leading to cyclopentanones bearing an α-hydroxy substituted quaternary center. In the presence of water, coordination of gold catalyst onto alkynyl moiety triggers hydration rather than a direct ring expansion, which followed by unprecedented Au-catalyzed α-ketol rearrangement. The details and the scope of this method are presented.

Bronsted acid catalyzed enantioselective semipinacol rearrangement for the synthesis of chiral spiroethers

A new twist: The catalytic asymmetric semipinacol rearrangement reaction of 2oxo allylic alcohols 1 in the presence of a catalytic amount of chiral phosphoric acid (R)-2a or its silver salt (R)-2b affords enantiomerically pure spiroethers 3.

1-Oxaspiro[4.4]nonan-6-ones. Synthetic access via oxonium ion technology, optical resolution, and conversion into enantiopure spirocyclic α,β-butenolides

A general approach to the synthesis of enantiomerically pure spirocyclic α,β-butenolides is presented where the fundamental framework is rapidly elaborated by acid- or bromonium ion-induced rearrangement of the carbinol derived by addition of 2-lithio-4,5-dihydrofuran to cyclobutanone. Subsequent resolution of the resulting ketones by either sulfoximine or mandelate acetal technology has been applied effectively. The availability of these building blocks makes possible in turn the acquisition of the enantiomers of dihydrofurans typified by 17, 35, and 38 and lactones such as 25 and 31, as well as the targeted title compounds. Complementary reductions of the early intermediates provide the added advantage that the α- and β-stereoisomeric carbinol series can be obtained on demand. These capabilities have been coordinated to allow the crafting of any member of the series in relatively few steps.

Synthesis and Molecular Structure of Belted Spirocyclic Tetrahydrofurans, A New Class of Preorganized Hosts for Cations

The preparation and binding properties of spirocyclic tetrahydrofurans 7-11 are described.The condensation of cyclopentanone with 5-lithio-2,3-dihydrofuran (12) provided an alcohol which readily rearranged to ketone 14 under acidic conditions. "Capping" of the carbonyl group in 14 so as to generate a second spiro tetrahydrofuran subunit gave rise to 7 and 8.Starting with cyclobutanone, 2-fold ring expansion involving 12 provided the key reactions leading to 22 and 23, which were "capped" as before.Crystal structure data are available for 9, 11, and 22.In addition, the variable-temperature NMR behaviour of 7 and 10 was quantified by means of 2-D measurements.A detailed analysis is presented that shows the gauche effect to be of major importance in dictating the major conformation adopted by these ionophores.The binding properti s of 7 - 11 have been assayed.Considerable variation was found, the efficiency being critically dependent upon the number of oxygen atoms, the relative stereochemistry of the C-O bonds, and the relative ease of conformational readjustment necessary to achieve proper organization around the oxophilic metal ion.