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| | (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid Basic information |
| Product Name: | (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid | | Synonyms: | (1S)-1,2,3,4-Tetrahydro-1-naphthalenecarboxylic Acid;D-(-)-1,2,3,4-Tetrahydro-1-naphthoic Acid;(S)-(-)-1,2,3,4-Tetrahydro-1-naphthoic acid(W.S);(1S)-1-Carboxy-1,2,3,4-tetrahydronaphthalene, (1S)-1,2,3,4-Tetrahydro-1-naphthoic acid;Palonosetron interMediater B;1-Naphthalenecarboxylic acid, 1,2,3,4-tetrahydro-,(1S)-;(S)-1, 2, 3, 4-Tetrahydronaphthoic acidCAS;(S)-1,2,3,4-Tetrahydro-1-naphthoic Acid,99%e.e. | | CAS: | 85977-52-2 | | MF: | C11H12O2 | | MW: | 176.21 | | EINECS: | | | Product Categories: | Carboxylic Acids & Deriv.;CHIRAL CHEMICALS;INTERMEDIATESOFPALONOSETRONHYDROCHLORIDE;Aromatics;Chiral Reagents;Intermediates | | Mol File: | 85977-52-2.mol |  |
| | (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid Chemical Properties |
| Melting point | 54-56°C | | Boiling point | 54-56°C | | density | 1.186±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform | | form | Solid | | pka | 4.28±0.20(Predicted) | | color | White | | InChI | InChI=1S/C11H12O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10H,3,5,7H2,(H,12,13)/t10-/m0/s1 | | InChIKey | VDLWTJCSPSUGOA-JTQLQIEISA-N | | SMILES | [C@@H]1(C(O)=O)C2=C(C=CC=C2)CCC1 | | CAS DataBase Reference | 85977-52-2(CAS DataBase Reference) |
| | (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid Usage And Synthesis |
| Chemical Properties | White Solid | | Uses | Intermediate in the preparation of Dipeptidyl Boronate Proteasome Inhibitors. | | Synthesis | General procedure for the synthesis of (S)-tetrahydronaphthalenecarboxylic acid from 1,2,3,4-tetrahydro-1-naphthalenecarboxylic acid: 15.6 g (0.1 mol) of 1,2,3,4-tetrahydronaphthalenecarboxylic acid and 29.8 g (0.1 mol) of quinine were added to 158 mL of a 50% (v/v) aqueous ethanol solution, and stirred for 30 min at 50 °C until complete dissolution. The progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent ratio of petroleum ether (PE):ethyl acetate (EA) = 1:2. Upon completion of the reaction, the reaction solution was cooled to below 0 °C overnight to promote crystallization. Subsequent to filtration, the solid was collected and dried. The dried solid was recrystallized with 90 mL of ethanol, crystallized again at 0 °C, diafiltrated and dried. The resulting product was dissolved in a mixture of 55 mL of 1 mol/L hydrochloric acid and 100 mL of ethyl acetate in a partitioning operation. The organic phase was dried and filtered and concentrated to obtain the crude product. Finally, the crude product was recrystallized from hexane to give 7.21 g of (S)-1,2,3,4-tetrahydronaphthalenecarboxylic acid in the form of white solid in 43.6% yield. | | References | [1] Patent: CN108084176, 2018, A. Location in patent: Paragraph 0093; 0102; 0103; 0104
[2] Arkiv foer Kemi, 1958, vol. 12, p. 161,165
[3] Patent: CN107382697, 2017, A |
| | (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid Preparation Products And Raw materials |
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