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| | 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE Basic information |
| Product Name: | 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE | | Synonyms: | 4-Oxo-1,5,6,7-tetrahydroindole;1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE;1,5,6,7-TETRAHYDRO-4H-INDOLE-4-ONE;1,5,6,7-TETRAHYDRO-INDOL-4-ONE;4-OXO-4,5,6,7-TETRAHYDROINDOLE;Tetrahydroindolone;4-0xo-4,5,6,7-tetrahydroindole;1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE 97+% | | CAS: | 13754-86-4 | | MF: | C8H9NO | | MW: | 135.16 | | EINECS: | | | Product Categories: | Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;Heterocyclic Compounds | | Mol File: | 13754-86-4.mol |  |
| | 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE Chemical Properties |
| Melting point | 188-190 °C (lit.) | | Boiling point | 311℃ | | density | 1.216 | | Fp | 150℃ | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | pka | 15.91±0.20(Predicted) | | form | powder to crystal | | color | White to Light yellow to Light orange | | InChI | InChI=1S/C8H9NO/c10-8-3-1-2-7-6(8)4-5-9-7/h4-5,9H,1-3H2 | | InChIKey | KASJZXHXXNEULX-UHFFFAOYSA-N | | SMILES | N1C2=C(C(=O)CCC2)C=C1 | | CAS DataBase Reference | 13754-86-4(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | HS Code | 2914390090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE Usage And Synthesis |
| Uses | • ;Reactant in synthesis of psammopemmin A as antitumor agent1• ;Reactant in synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions2• ;Reactant in preparation of tricyclic indole and dihydroindole derivatives as inhibitors of guanylate cyclase3• ;Reactant in preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles4• ;Reactant in enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids foll | | Uses | 1,5,6,7-Tetrahydro-4H-indol-4-one, is a versatile building block used for the synthesis of more complex pharmaceutical compounds. It can be used for the preparation of Psammopemmin A. | | General Description | Iodination of 1,5,6,7-tetrahydro-4H-indol-4-one using 1-chloromethyl--4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra-fluoroborate) yields α-iodo derivative as the main product. | | Synthesis | The general procedure for the synthesis of 1,5,6,7-tetrahydro-4H-indol-4-one from 6,7-dihydro-4(5H)-benzofuranone is as follows: 6,7-dihydro-4(5H)-benzofuranone (0.10 g, 0.73 mmol) was dissolved in 20% aqueous ethanol (ca. 2 mL) along with the corresponding amine (3 equiv.) in an airtight tube at 150°C, respectively, and was Heating for 12 h or 36 h, respectively. Upon completion of the reaction, the reaction mixture was poured into water (10 mL) and the resulting aqueous solution was extracted with dichloromethane (3 x 10 mL). The organic extracts were combined, dried with anhydrous magnesium sulfate and concentrated to give a brown residue. This residue was purified by silica gel column chromatography with a solvent mixture of ethyl acetate/petroleum ether as eluent. | | References | [1] Heterocycles, 1984, vol. 22, # 10, p. 2313 - 2316
[2] Tetrahedron Letters, 2012, vol. 53, # 33, p. 4276 - 4279
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 1, p. 341 - 343 |
| | 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE Preparation Products And Raw materials |
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