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
• Article Data: 6

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

Description

1-Oxaspiro[4.4]nonan-6-one is a chemical compound characterized by the molecular formula C9H14O2. It features a cyclic ketone with a spiro ring structure, which is centered around a central oxygen atom. This unique structural attribute endows it with potential biological activity, making it a valuable component in the synthesis of pharmaceuticals and fragrances. Additionally, it serves as a versatile building block in the creation of other organic compounds, thereby expanding its applications across the chemical and pharmaceutical industries.

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

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.

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.

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.