63049-05-8

Basic information

• Product Name: Spiro[3.3]heptan-1-one
• Synonyms: Spiro[3.3]heptan-1-one
• CAS NO: 63049-05-8
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.15
• Mol File: 63049-05-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Spiro[3.3]heptan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[3.3]heptan-1-one(63049-05-8)
• EPA Substance Registry System: Spiro[3.3]heptan-1-one(63049-05-8)

Safety Data

• Hazardous Substances Data: 63049-05-8(Hazardous Substances Data)

Usage

General Description

Spiro[3.3]heptan-1-one is a bicyclic ketone compound with a unique spiro-fused seven-membered ring structure. It is used as a building block in the synthesis of various organic compounds and pharmaceuticals due to its versatile reactivity and functional group compatibility. Spiro[3.3]heptan-1-one has been used as a precursor in the synthesis of natural products and medicinal compounds. Its unique structure and reactivity have also made it a subject of interest in the development of new chemical reactions and synthetic methodologies. Additionally, spirotetramat, a derivative of spirotetronate, has insecticidal and acaricidal activities and is used as a pesticide in agriculture.

Upstream product

• 16764-72-0 cyclobutylidenecyclopropane 
• 1191-95-3 cyclobutanone 
• 10575-90-3 N-nitroso-N-cyclopropylurea 
• 54022-19-4 diazocyclopropane 
• 14633-54-6 cyclopropylphenylsulfide 

Downstream Products

• 1823960-41-3 spiro[3.3]heptan-1-ol 
• 16764-72-0 cyclobutylidenecyclopropane 
• 10563-10-7 Bicyclo<3.2.0>hept-1(5)-en 
• 20968-70-1 1,2-dimethylenecyclopentane 
• 20036-34-4 1-methylenespiro[2.3]hexane 
• 160246-09-3 5-(4-nitrobenzenesulfonimido)dispiro<3.1.3.2>undecane 
• 160246-10-6 (5R*)-6-(4-nitrobenzenesulfonimido)dispiro<3.0.4.2>undecane 
• 84565-28-6 5-azaspiro[3.4]octan-6-one 

Relevant articles and documents

Competitive 1,2-C Atom Shifts in the Strained Carbene Spiro[3.3]hept-1-ylidene Explained by Distinct Ring-Puckered Conformers

Spiro[3.3]hept-1-ylidene is a markedly strained carbene reaction intermediate that was generated by high-vacuum flash pyrolysis (HVFP) of the corresponding p-tosylhydrazone sodium salt. Five hydrocarbons were produced from the Bamford-Stevens reactant in 82% overall yield. The carbene undergoes two [1,2]-sigmatropic rearrangements via competing 1,2-C atom shifts. Ring-contraction yields cyclopropylidenecyclobutane, while ring-expansion affords bicyclo[3.2.0]hept-1(5)-ene. The ring contraction is regiospecific despite the formation of some 1-methylenespiro[2.3]hexane. It does not originate from the carbene under HVFP conditions. Instead, it comes from a methylenecyclopropane-type rearrangement of chemically activated cyclopropylidenecyclobutane. Similarly, some chemically activated bicyclo[3.2.0]hept-1(5)-ene rearranges to 1,2-dimethylenecyclopentane via electrocyclic ring-opening. Accounting for the conversion of primary products to secondary ones, relative yields indicate that ring-contraction within the carbene prevails over ring-expansion by a factor of 6.7:1. Computational chemistry was used to assess the structures, conformations, energies, strain energies, transition states, and activation energies of these rearrangements with the goal of explaining product selectivities. The dual-ringed carbene is predicted to assume four distinct geometric conformations that have a bearing on transition-state selection. The reactive cyclobutylidene units of two conformers are significantly puckered, like cyclobutylidene itself, while those of the other two are flatter. The selectivity of the title carbene is compared with that of spiro[2.3]hex-4-ylidene.

Cyclopropylidenecyclanes Oxydation par l'acide peroxycarboximidique

The title reaction gives a mixture of four compounds .A 2-cyclohexyllideneoxetane is invoked as intermediary to account for the unusual lactone formation.