51716-63-3

Basic information

• Product Name: CIS-BICYCLO[3.3.0]OCTANE-3,7-DIONE
• Synonyms: cis-Bicyclo(3.3.o)octane-3,7-dione;Tetrahydro-2,5(1H,3H)-pentalenedione;CIS-BICYCLO[3.3.0]OCTANE-3,7-DIONE;cis-tetrahydropentalene-2,5(1H,3H)-dione;2,5(1H,3H)-Pentalenedione, tetrahydro-, cis-;(S,S)-TETRAHYDROPENTALENE-2,5(1H,3H)-DIONE;bicyclo[3.3.0]octane-3,7-dione;(1α,5α)-Bicyclo[3.3.0]octane-3,7-dione
• CAS NO: 51716-63-3
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16
• EINECS: 257-357-2
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 51716-63-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 83-86 °C(lit.)
• Boiling Point: 268.277 °C at 760 mmHg
• Flash Point: 99.36 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DCM, Ethyl Acetate, Methanol
• CAS DataBase Reference: CIS-BICYCLO[3.3.0]OCTANE-3,7-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-BICYCLO[3.3.0]OCTANE-3,7-DIONE(51716-63-3)
• EPA Substance Registry System: CIS-BICYCLO[3.3.0]OCTANE-3,7-DIONE(51716-63-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 51716-63-3(Hazardous Substances Data)

Usage

Uses

cis-Tetrahydro-2,5(1H,3H)-pentalenedione is an intermediate in the synthesis of Loganin (L469405), an iridoid glycoside that exhibits protective effects against hepatic injury and other diabetic complications associated with abnormal metabolic states and inflammation caused by oxidative stress and advanced glycation endproduct formation. A potential anti-amnesic agent.

Synthesis Reference(s)

Synthesis, p. 529, 1984 DOI: 10.1055/s-1984-30893Tetrahedron, 38, p. 63, 1982 DOI: 10.1016/0040-4020(82)85046-1

InChI:InChI=1/C8H10O2/c9-7-1-5-2-8(10)4-6(5)3-7/h5-6H,1-4H2/t5-,6+

Upstream product

• 768-48-9 4-acetoxy-cyclopentenone 
• 78698-09-6 Vossen's Red Salt 
• 78698-10-9 Tetramethyl 3-Hydroxy-7-oxobicyclo<3.3.0>octa-1,3,5-triene-2,4,6,8-tetracarboxylate Sodium Salt 
• 102065-09-8 tetra-tert-butyl cis 3,7-dihydroxy-cis-bicyclo<3.3.0>octa-2,6-diene-2,4,6,8-tetracarboxylate 
• 92007-38-0 cis-bicyclo[3.3.0]octane-3,7-dione 3,7-bis(2',2'-dimethylpropylidene) acetal 
• 102065-01-0 tetra-tert-butyl 3,7-dimethoxy-cis-bicyclo<3.3.0>-octa-2,6-diene-2,4,6,8-tetracarboxylate 
• 68703-09-3 tetramethyl cis,cis-3,7-dihydroxybicyclo[3.3.0]octa-2,6-diene-2,4-exo,6,8-exo-tetracarboxylate 
• 82416-02-2 C₁₆H₁₆O₁₀^(2-)*2Na⁽¹⁺⁾ 
• 68703-09-3 tetramethyl 3,7-dihydroxybicyclo[3.3.0]octa-2,6-diene-2,4,6,8-tetracarboxylate 
• 556-56-9 allyl iodid 
• 58648-36-5 Weiss tetraester 
• 54928-90-4 2,4,6,8-Tetrakis-aethoxycarbonyl-cis-bicyclo<3.3.0>octa-3,7-dion 

Downstream Products

• 112755-94-9 (3a'R,6a'S)-5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-one 
• 92007-38-0 cis-bicyclo[3.3.0]octane-3,7-dione 3,7-bis(2',2'-dimethylpropylidene) acetal 
• 89074-10-2 2-Phenylsulfonylbicyclo<3.3.0>octane-3,7-dione 
• 169525-04-6 2α,3aβ,5α,6aβ-N,N'-dibenzyloctahydropentalene-2,5-diamine 
• 560117-83-1 7-(4-(2-methoxyphenyl)piperazin-1-yl)bicyclo[3.3.0]octane-3-one 
• 1227742-53-1 C₁₈H₂₁ClO₄S 
• 51716-62-2 (3aR,6aS)-7,7-(ethylidene acetal)bicyclo[3.3.0]octan-3-one 
• 69552-45-0 C₁₂H₁₈O₄ 
• 19915-11-8 (3aRS,6aSR)-hexahydro-2(1H)-pentalenone 
• 791-28-6 Triphenylphosphine oxide 
• 139607-41-3 cis-3,7-bis(cyclopenta-2,4-dien-1-ylidene)bicyclo<3.3.0>octane 
• 197250-70-7 (4aS,7aS)-tetrahydro-1H-cyclopenta[c]pyridin-3,6(2H,4H)-dione 

Relevant articles and documents

Bicycloocta-1,5-diene-3,7-dione

Bicycloocta-1,5-diene-3,7-dione (5) has been prepared by the hydrolysis-decarboxylation of tetramethyl 3-hydroxy-7-oxobicycloocta-1,3,5-triene-2,4,6,8-tetracarboxylate sodium salt (2), which was obtained in one step from "Vossen's Red Salt" (1).

DIHYDROPTERIDINONE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

Dihydroperidinone derivatives, preparation process and pharmaceutical use thereof are disclosed. Specially, new dihydroperidinone derivatives represented by general formula (I), wherein each substituent of the general formula (I) is defined as in the description, their preparation process, pharmaceutical compositions comprising said derivatives and their use as therapeutical agents, especially as Plk kinase inhibitors are disclosed.

Versatile Route to centro-Substituted Triquinacene Derivatives: Synthesis of 10-Phenyltriquinacene

(Equation Presented) A versatile route to prepare centro-substituted triquinacene derivatives (1, R = various substituents), as exemplified by the preparation of 10-phenyltriquinacene (1, R = Ph), is reported. The quaternary, centro substituent (C-10) was installed by a trimethylsilyl chloride-promoted conjugate addition reaction of an organocuprate, derived from phenylmagnesium bromide, and the protected bicyclic enone (11). The resultant trimethylsilyl enol ether was then converted regioselectively to the C-2-allylated conjugate addition products (13, R = Ph). The allyl moiety, following oxidative cleavage of the carbon-carbon double bond, was used to elaborate the tricyclic ring system by an intramolecular aldol/ acetal deprotection reaction. The product of this reaction was then converted to the target compound using a standard series of functional group transformation reactions.