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ChemicalBook--->CAS DataBase List--->18720-35-9

18720-35-9

18720-35-9 Structure

18720-35-9 Structure
IdentificationBack Directory
[Name]

BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER
[CAS]

18720-35-9
[Synonyms]

o[2.2.2]octane-1-carboxyL
4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-
1-Carboxy-4-(Methoxycarbonyl)bicyclo[2.2.2]octane
Bicyclo [2.2.2] octane-1,4-cyclohexanedicarboxylate
4-(Methoxycarbonyl)bicyclo[2.2.2]octan-1-carboxylic Acid
4-(METHOXYCARBONYL)BICYCLO[2.2.2]OCTANE-1-CARBOXYLICACID
Monomethyl Hydrogen Bicyclo[2.2.2]octane-1,4-dicarboxylate
Bicyclo[2.2.2]octane-1,4-dicarboxylIic acid hemimethyl este
BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER
Bicyclo [2.2.2]octane-1,4-dicarboxylic acid, 1-methyl ester
Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, monomethyl ester
Bicyclo[2.2.2]octane-1,4-dicarboxylIic acid hemimethyl ester
4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid, >=98%
Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, monomethyl ester 97%
4- (methoxy carbonyl) double ring [2.2.2] octane -1- carboxylic acid
[EINECS(EC#)]

814-024-1
[Molecular Formula]

C11H16O4
[MDL Number]

MFCD08274673
[MOL File]

18720-35-9.mol
[Molecular Weight]

212.24
Chemical PropertiesBack Directory
[Melting point ]

186.0 to 190.0 °C
[Boiling point ]

322.5±42.0 °C(Predicted)
[density ]

1.307±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

soluble in Methanol
[form ]

powder to crystaline
[pka]

4.77±0.10(Predicted)
[color ]

White to Almost white
[InChI]

InChI=1S/C11H16O4/c1-15-9(14)11-5-2-10(3-6-11,4-7-11)8(12)13/h2-7H2,1H3,(H,12,13)
[InChIKey]

KBZVAQVEHVGIEI-UHFFFAOYSA-N
[SMILES]

C12(C(OC)=O)CCC(C(O)=O)(CC1)CC2
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

25-36
[Safety Statements ]

26-45
[RIDADR ]

UN 2811 6.1 / PGIII
[WGK Germany ]

3
[HS Code ]

2917200090
Hazard InformationBack Directory
[Uses]

4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic Acid has been used as a reactant for the preparation of bicyclo-octyltriazole inhibitors of HSD1 for metabolic syndrome treatment.
[Synthesis]

dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

1459-96-7

BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER

18720-35-9

General procedure for the synthesis of 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1,4-dicarboxylic acid from dimethyl bicyclo[2.2.2]octane-1-carboxylate: a mixture of 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (20 g) and potassium hydroxide (5.5 g) in methanol/water (10:1, 106 mL) was heated to reflux overnight. After the reaction was completed, it was cooled to room temperature and concentrated. The residue was diluted with ethyl acetate and extracted with 1N aqueous sodium hydroxide (2 x 100mL). The organic phase was dried with magnesium sulfate, filtered and concentrated to give the starting material as a white solid. The combined aqueous phases were adjusted to pH 1-2 with 2N aqueous hydrochloric acid and extracted with ethyl acetate (4 x 250mL). The combined turbid organic phases were filtered through a slot filter, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated to afford 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid as a colorless solid (13.1 g, 70% yield). Mass spectral analysis showed [MH]+ = 213.

[References]

[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5731 - 5737
[2] Patent: WO2006/128184, 2006, A2. Location in patent: Page/Page column 164-165
[3] Patent: WO2008/63671, 2008, A2. Location in patent: Page/Page column 177-178
[4] Patent: WO2014/159802, 2014, A1. Location in patent: Paragraph 00189
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 6, p. 1558 - 1568
Spectrum DetailBack Directory
[Spectrum Detail]

BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER(18720-35-9)1HNMR
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