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| | NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE Basic information |
| Product Name: | NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE | | Synonyms: | (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-Methanoisobenzofuran-1,3-dione;(3aα,4β,7β,7aα)-Hexahydro-4,7-Methanoisobenzofuran-1,3-dione;NSC 59061;Norborane-2-exo,3-exo-dicarboxylic acid anhydride;(3aR,4S,7R,7aS)-Hexahydro-4,7-Methanoisobenzofuran-1,3-dione;(3aR,7aS)-hexahydro-4,7-methano-2-benzofuran-1,3-dione;2,3-Norbornanedicarboxylic anhydride;NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE | | CAS: | 14166-28-0 | | MF: | C9H10O3 | | MW: | 166.17 | | EINECS: | | | Product Categories: | Heterocycles;Miscellaneous Reagents | | Mol File: | 14166-28-0.mol |  |
| | NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE Chemical Properties |
| Melting point | 80-82 °C(Solv: ethanol (64-17-5)) | | Boiling point | 325.2±11.0 °C(Predicted) | | density | 1.345 | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Chloroform | | form | Solid | | color | Light Yellow | | InChI | InChI=1/C9H10O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h4-7H,1-3H2/t4-,5+,6+,7- | | InChIKey | LQOPXMZSGSTGMF-RNGGSSJXNA-N | | SMILES | C1(=O)[C@]2([H])[C@@]([H])([C@]3([H])C[C@@]2([H])CC3)C(=O)O1 |&1:2,4,6,9,r| |
| | NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE Usage And Synthesis |
| Chemical Properties | Light Yellow Solid | | Uses | exo-Norbornane-2,3-dicarboxylic Anhydride (cas# 14166-28-0) is a compound useful in organic synthesis. | | Synthesis | General procedure for the synthesis of (3aR,4S,7R,7aS)-rel-hexahydro-4,7-methanoisobenzofuran-1,3-dione from cis-5-norbornene-exo-2,3-dicarboxylic anhydride: 200 g of cis-5-norbornene-exo-2,3-dicarboxylic anhydride (from step 2) was mixed with 1.5 L of toluene, heated until completely dissolved, and then transferred to a 4-L high pressure reactor. 10 g of Pd/Pt catalyst was added to the reactor and the system was purged under 10 bar hydrogen pressure for 5 minutes. After purging, the hydrogen pressure was adjusted to 12 bar and the hydrogenation reaction was carried out at 160°C and 20 bar hydrogen pressure. After the reaction lasted 70 minutes, the catalyst was removed. The reaction mixture was transferred to 5 L of hexane and after filtration and drying, 182 g of white solid product (compound 4) was obtained. The structure of the product was confirmed by NMR (1H and 13C NMR, JEOL JNM-LA400) and IR spectroscopy (AVATAR 360FT-IR). The relevant spectral data are displayed in Figures 1, 2, 4 and 5, respectively. | | References | [1] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3953 - 3959
[2] Organic Preparations and Procedures International, 1999, vol. 31, # 2, p. 220 - 222
[3] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300
[4] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 12, p. 2139 - 2151
[5] Monatshefte fur Chemie, 2004, vol. 135, # 7, p. 839 - 847 |
| | NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE Preparation Products And Raw materials |
| Raw materials | Carbic anhydride-->CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE-->Toluene-->Hydrogen | | Preparation Products | (3aR,4R,7S,7aS)-2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]hexahydro-1H-4,7-methanoisoindole-1,3-dione-->Bicyclo[2.2.1]heptane-2,3-dicarboxylic acid, (1R,2S,3R,4S)--->(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione |
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