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CAS No. : | 13105-78-7 | MDL No. : | MFCD16661706 |
Formula : | C12H15NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 189.25 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 12h; | 7-(2-(Benzyl(prop-2-yn-l-yl)amino)ethoxy)-2-phenyl-4H-chromen-4-one (Acl6): To a well stirred solution of <strong>[6665-86-7]7-hydroxyflavone</strong>s le (2.9mmol, 0.7g), 2-(benzyl(prop-2-yn-l-yl)amino)ethanol (2.9mmol, 0.56g) and PPh3 (0.77g, lequiv.) in THF (10ml) at room temperature, was added DIAD (0.58ml, lequiv.) dropwise. The reaction mixture was then stirred for 12 h. The reaction mixture was evaporated to give a brown crude reaction mixture. Purification was performed by flash column chromatography on silica gel with acetone in DCM (1 :50) as eluent to furnish titled compound (0.42g, 35%). 1H NMR (500 MHz, CHLOROFORM-i/) delta ppm 2.30 (t, J=2.20 Hz, 1 H), 3.07 (t, J=5.61 Hz, 2 H), 3.48 (d, J=2.44 Hz, 2 H), 3.79 (s, 2 H), 4.21 (t, J=5.61 Hz, 2 H), 6.77 (s, 1 H), 6.95 - 7.01 (m, 2 H), 7.27 - 7.29 (m, 1 H), 7.31 - 7.35 (m, 2 H), 7.37 - 7.40 (m, 2 H), 7.50 - 7.55 (m, 3 H), 7.88 - 7.93 (m, 2 H), 8.13 (d, J=8.78 Hz, 1 H); 13C NMR (101 MHz, CHLOROFORM-i/) delta ppm 42.61 , 51.72, 58.53, 67.22, 70.04, 101.1 1 , 107.54, 1 14.72, 1 17.93, 126.16, 127.07, 127.46, 128.42, 128.98, 129.12, 131.39, 131.89, 157.93, 163.03, 163.26, 177.82; LRMS (ESI) m/z 410 [M+H]+; HRMS (ESI) calcd for C27H24 O3 [M+H]+ 410.1756, found 410.1750. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.8% | Stage #1: N-benzyl-N-(2-hydroxyethyl)prop-2-yn-1-amine With pyridine; thionyl chloride In dichloromethane at 20℃; for 2h; Stage #2: With sodium azide In N,N-dimethyl-formamide at 80℃; for 8h; |