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| | BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER Basic information |
| Product Name: | BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER | | Synonyms: | Bicyclo[2.2.2]octane-1,4-dicarboxylIic 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;4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-;1-Carboxy-4-(Methoxycarbonyl)bicyclo[2.2.2]octane;4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid, >=98%;4-(Methoxycarbonyl)bicyclo[2.2.2]octan-1-carboxylic Acid;4-(METHOXYCARBONYL)BICYCLO[2.2.2]OCTANE-1-CARBOXYLICACID | | CAS: | 18720-35-9 | | MF: | C11H16O4 | | MW: | 212.24 | | EINECS: | 814-024-1 | | Product Categories: | Carboxylic Acids;Carboxylic Acids;Fused Ring Systems | | Mol File: | 18720-35-9.mol | ![BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER Structure](CAS/GIF/18720-35-9.gif) |
| | BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER Chemical Properties |
| 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 |
| Hazard Codes | T | | Risk Statements | 25-36 | | Safety Statements | 26-45 | | RIDADR | UN 2811 6.1 / PGIII | | WGK Germany | 3 | | HS Code | 2917200090 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Eye Irrit. 2 |
| | BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER Usage And Synthesis |
| 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 | 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 |
| | BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER Preparation Products And Raw materials |
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