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Chemical Structure| 18940-21-1 Chemical Structure| 18940-21-1

Structure of 18940-21-1

Chemical Structure| 18940-21-1

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Product Details of [ 18940-21-1 ]

CAS No. :18940-21-1
Formula : C14H17NO
M.W : 215.29
SMILES Code : O=C1C=C(NC2=CC=CC=C2)CC(C)(C)C1
MDL No. :MFCD00128479

Safety of [ 18940-21-1 ]

Application In Synthesis of [ 18940-21-1 ]

* 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 [ 18940-21-1 ]

[ 18940-21-1 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 17115-51-4 ]
  • [ 120-57-0 ]
  • [ 18940-21-1 ]
  • [ 1265632-03-8 ]
YieldReaction ConditionsOperation in experiment
72% at 90℃; for 12h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 2
  • [ 17115-51-4 ]
  • [ 3132-99-8 ]
  • [ 18940-21-1 ]
  • [ 1265631-99-9 ]
YieldReaction ConditionsOperation in experiment
81% at 90℃; for 10h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 3
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 459-57-4 ]
  • [ 1265631-94-4 ]
YieldReaction ConditionsOperation in experiment
80% at 90℃; for 9h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 4
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 99-61-6 ]
  • [ 1265631-96-6 ]
YieldReaction ConditionsOperation in experiment
80% at 90℃; for 9h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 5
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 555-16-8 ]
  • [ 1265631-97-7 ]
YieldReaction ConditionsOperation in experiment
83% at 90℃; for 8h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 6
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 587-04-2 ]
  • [ 1265631-98-8 ]
YieldReaction ConditionsOperation in experiment
77% at 90℃; for 8h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 7
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 446-52-6 ]
  • [ 1265632-02-7 ]
YieldReaction ConditionsOperation in experiment
75% at 90℃; for 12h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 8
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 591-31-1 ]
  • [ 1239983-01-7 ]
YieldReaction ConditionsOperation in experiment
78% at 90℃; for 10h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 9
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 6287-38-3 ]
  • [ 1265631-95-5 ]
YieldReaction ConditionsOperation in experiment
78% at 90℃; for 9h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 10
  • [ 17115-51-4 ]
  • [ 18940-21-1 ]
  • [ 456-48-4 ]
  • [ 1265631-93-3 ]
YieldReaction ConditionsOperation in experiment
85% at 90℃; for 8h;Neat (no solvent); Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4.
  • 11
  • [ 18940-21-1 ]
  • [ 59046-72-9 ]
  • 5,5-dimethyl-2-(3-phenyl-1H-isochromen-1-yl)-3-(phenylamino)cyclohex-2-enone [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With silver nitrate; In N,N-dimethyl acetamide; at 60℃; for 12h;Schlenk technique; The substrate <strong>[59046-72-9]2-(phenylethynyl)benzaldehyde</strong> (1a, 0.5 mmol, 0.1030 g), 5,5-dimethyl-3-(phenylamino)cyclohex-2-enone (2a, 1.0 mmol, 0.2151 g, 2 equiv) and AgNO3 (0.05 mmol, 0.0085 g, 10 mol %) were added to a 25 mL Schlenk tube, followed by addition of dry DMA (2.0 mL). The mixture was stirred at 60 C for 12 h. The solution was then quenched by H2O and extracted with EtOAc, the combined organic layers were dried over Na2SO4, filtered, and evaporated under vaccum. The residue was purified by column chromatography on silica gel (eluent: light petroleum ether: ethyl acetate, V: V = 5: 1) to afford the desired product 5,5-dimethyl-2-(3-phenyl-1H-isochromen-1-yl)-3-(phenylamino)cyclohex-2-enone (3a). 4.2.1. 5,5-dimethyl-2-(3-phenyl-1H-isochromen-1-yl)-3-(phenylamino)cyclohex-2-enone (3a) Yellow solid, mp: 161.7-162.2 C; IR (neat, ν, cm-1): 3348, 2955, 2865, 1636, 1024 cm-1; 1H NMR (400 MHz, CDCl3) d 7.74 (d, J = 7.1 Hz, 2H), 7.66 (s, 1H), 7.41-7.31 (m, 3H), 7.24 (dd, J = 16.5, 8.5 Hz, 3H), 7.18-7.08 (m, 3H), 7.02 (d, J = 7.4 Hz, 1H), 6.87 (d, J = 7.7 Hz, 2H), 6.78 (s, 1H), 6.53 (s, 1H), 2.58-2.37 (m, 4H), 1.18 (s, 3H), 1.14 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 193.7, 160. 8, 154.1, 137.6, 133.6, 133.0, 129.7, 128.7, 128.5, 127.9, 127.8, 126.5, 125.7, 125.1, 124.8, 123.5, 123.1, 106.1, 102.0, 73.7, 49.8, 40.5, 32.2, 28.3, 27.8; HRMS (ESI) m/z: Found: 444.1943. Calcd for C29H27NO2: (M+Na)+ 444.1934.
  • 12
  • [ 943835-77-6 ]
  • [ 18940-21-1 ]
  • 2-(7-fluoro-3-phenyl-1H-isochromen-1-yl)-5,5-dimethyl-3-(phenylamino)cyclohex-2-enone [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With silver nitrate; In N,N-dimethyl acetamide; at 60℃; for 12h;Schlenk technique; General procedure: The substrate 2-(phenylethynyl)benzaldehyde (1a, 0.5 mmol, 0.1030 g), 5,5-dimethyl-3-(phenylamino)cyclohex-2-enone (2a, 1.0 mmol, 0.2151 g, 2 equiv) and AgNO3 (0.05 mmol, 0.0085 g, 10 mol %) were added to a 25 mL Schlenk tube, followed by addition of dry DMA (2.0 mL). The mixture was stirred at 60 C for 12 h. The solution was then quenched by H2O and extracted with EtOAc, the combined organic layers were dried over Na2SO4, filtered, and evaporated under vaccum. The residue was purified by column chromatography on silica gel (eluent: light petroleum ether: ethyl acetate, V: V = 5: 1) to afford the desired product 5,5-dimethyl-2-(3-phenyl-1H-isochromen-1-yl)-3-(phenylamino)cyclohex-2-enone (3a).
 

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