98516-59-7

Basic information

• Product Name: spiro(pentacyclo[5.3.0.0~2,5~.0~3,9~.0~4,8~]decane-10,2'-[1,3]-dioxolane)-2-carboxylic acid
• Synonyms: spiro(pentacyclo[5.3.0.0~2,5~.0~3,9~.0~4,8~]decane-10,2'-[1,3]-dioxolane)-2-carboxylic acid
• CAS NO: 98516-59-7
• Molecular Formula: C13H14O4
• Molecular Weight: 234.24786
• Mol File: 98516-59-7.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: spiro(pentacyclo[5.3.0.0~2,5~.0~3,9~.0~4,8~]decane-10,2'-[1,3]-dioxolane)-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: spiro(pentacyclo[5.3.0.0~2,5~.0~3,9~.0~4,8~]decane-10,2'-[1,3]-dioxolane)-2-carboxylic acid(98516-59-7)
• EPA Substance Registry System: spiro(pentacyclo[5.3.0.0~2,5~.0~3,9~.0~4,8~]decane-10,2'-[1,3]-dioxolane)-2-carboxylic acid(98516-59-7)

Safety Data

• Hazardous Substances Data: 98516-59-7(Hazardous Substances Data)

Upstream product

• 98516-58-6 C₁₅H₁₈O₄ 
• 2435-32-7 6,7-epoxy-1,4,4a,6,7,8a-hexahydro-1,4-methano-naphthalene-5,8-dione 
• 51175-59-8 norbornenoquinone 
• 121312-57-0 ethyl 5-oxo-tricyclo[5.2.1.0.]deca-3,8-diene-2-carboxylate 
• 56689-09-9 ethyl pentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decan-6-one-8-carboxylic acid 

Relevant articles and documents

NUCLEOPHILIC ELIMINATIVE RING FISSION OF BRIDGEHEAD SUBSTITUTED 1,3-BISHOMOCUBYL ACETATES

The base induced cage fission of three different types of functionalized bridgehead substituted 1,3-bishomocubyl acetates, viz A, B and C is described.The synthesis of two 6-functionalized 1,3-bishomocubyl 4-acetates (type A), viz 4-acetoxypentacyclo2,5.03,9.04,8>decan-6-one 5 and its ethylene acetal 6 has been accomplished starting from the readily available Diels-Alder adduct 4.The synthesis of three 1,3-bishomocubyl 8-acetates (type B), viz 8-acetoxypentacyclo2,5.03,9.04,8>decan-6-one 15, its ethylene acetal 16 and the parent acetate 20has been carried out starting from the cyclopentadiene-benzoquinone adduct 7.Base induced homoketonization of 6, 16 and 20 leads regio- and stereospecifically to the thermodynamically favored half cage ketones 22, 28 and 31, respectively.In constrast, the cage opening of the β-ketoacetates 5 and 15 is essentially directed by the β-ketone function.In the case of 5, regiospecific cleavage of the central C4-C5 bond is observed producing in a stereospecific manner diketone 25 in quantitative yield.Under similar conditions, acetate 15 gives a complex mixture of cage opened products arising from further fragmentation of the initially formed diketone 34.Deuterium labeling experiments reveal an anti-Bredt behavior of half cage ketones 28 and 31.The synthesis of a bridgehead acetate of type C has been accomplished by stereoselective reduction of ketone acetate 5 with LiAlH(t-OBu)3 followed by mesylation.A mixture of epimers 36a and 36b (ratio 1:4) is obtained from which the predominant anti-epimer 36b could be isolated.An X-ray analysis established its structure.Base induced cage fission of 36b leads regiospecifically totetracyclo2,5.04,8>decenone 37.In constrast the syn-epimer 36a, under similar conditions, only affords the bridgehead alcohol 38.