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Chemical Structure| 65857-18-3 Chemical Structure| 65857-18-3

Structure of 65857-18-3

Chemical Structure| 65857-18-3

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Product Details of [ 65857-18-3 ]

CAS No. :65857-18-3
Formula : C9H16O2
M.W : 156.22
SMILES Code : O=C1CC(C(C)(C)C)OCC1
MDL No. :MFCD19650687

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Application In Synthesis of [ 65857-18-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 65857-18-3 ]

[ 65857-18-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 105486-72-4 ]
  • [ 65857-18-3 ]
  • [ 1520889-38-6 ]
YieldReaction ConditionsOperation in experiment
2% A mixture of 2-tert-butyldihydro-2H-pyran-4(3H)-one (0.3 g, 1.92 mmol) xantphos (22.2 mg, 38.4 muetaiotaomicron) and methyl 2-bromobenzoate (330 mg, 1.54 mmol), cesium carbonate (813 mg, 2.5 mmol), and Pd2(dba)3 (17.6 mg, 19.2 muetaiotaomicron), in toluene (2.0 mL) was placed under argon atmosphere and stirred at 90C for 15 h. The reaction mixture was pre-absorbed onto silica and purified by flash chromatography (Si02, 0% to 50% EtOAc in hexanes) to afford a crude oil (137 mg). The crude oil was dissolved in a solution of ammonia in methanol (7M, 2mL). The reaction mixture was heated at 140C in a microwave reactor for lh. The precipitate was filtered and dried in vacuo to afford 2-tert-butyl-l,2,4,10-tetrahydro-3-oxa-10-aza-phenanthren-9-one as a white solid (34 mg, 7%). H NMR (DMSO-d6) : 1 1.19 (br. s, 1H), 8.18 (dd, J = 7.9, 1.1 Hz, 1H), 7.61 - 7.77 (m, 1H), 7.40 (d, J = 7.9 Hz, 1H), 7.45 (d, J = 7.6 Hz, 1H), 4.94 (d, J = 14.0 Hz, 1H), 4.59 (dt, J = 14.2, 2.2 Hz, 1H), 3.30 - 3.37 (m, 1H), 2.36 - 2.55 (m, 2H), 0.94 (s, 9H). MS calcd. for Ci6Hi9N02 [(M+H)+] 258.4, obsd. 258.1. 7-teri-Butyl- 1 -methyl-5 ,6 ,7 ,9-tetrahydro- 1 H-8 -oxa- 1 ,2 ,5 -triaza-cyclopenta[a]naphthalen- 4-one was synthesized following the procedure in Example 7. From 2-tert-butyl-tetrahydro- pyran-4-one and 5-bromo-lH-pyrazole-4-carboxylic acid ethyl ester: 7-tert-butyl-l-methyl- 5,6,7,9-tetrahydro-lH-8-oxa-l ,2,5-triaza-cyclopenta[a]naphthalen-4-one was obtained as a white solid (25 mg, 2%). H NMR (DMSO-d6) delta: 10.88 (s, 1H), 7.89 (s, 1H), 5.18 (d, J = 14.0 Hz, 1H), 4.81 (d, J = 14.0 Hz, 1H), 3.98 (s, 3H), 0.93 (s, 9H). MS calcd. for Ci4Hi9N302 [(M+H)+] 262.3, obsd. 262.
 

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