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Chemistry
Catalysis Chemistry
Diketone Ligands
5-(4-(Methylthio)phenyl)cyclohexane-1,3-dione
Chemistry
Catalysis Chemistry
Diketone Ligands

[ CAS No. 144128-74-5 ] {[proInfo.proName]}

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Chemical Structure| 144128-74-5
Chemical Structure| 144128-74-5
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Product Details of [ 144128-74-5 ]

CAS No. :144128-74-5 MDL No. :
Formula : C13H14O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 234.31 Pubchem ID :-
Synonyms :

Safety of [ 144128-74-5 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 144128-74-5 ]

* 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 [ 144128-74-5 ]

[ 144128-74-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 4743-17-3 ]
  • [ 144128-74-5 ]
  • [ 144155-17-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1.) DMF, RT, 1 h, 2.) DMF, 90 deg C, 4 h; Yield given. Multistep reaction;
Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]
  • 2
  • [ CAS Unavailable ]
  • [ 144128-74-5 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid for 4.5h; Heating;
Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]
  • 3
  • [ CAS Unavailable ]
  • [ 144128-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: EtONa / ethanol / 6 h / Heating 2: 2 N NaOH / 2 h / Heating 3: 5 N H2SO4 / 4.5 h / Heating
Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]
  • 4
  • [ 144128-74-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) 50percent NaH / 1.) DMF, RT, 1 h, 2.) DMF, 90 deg C, 4 h 2: 81 percent / ethanol / 1.5 h / Heating
Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]
  • 5
  • [ CAS Unavailable ]
  • [ 144128-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2 N NaOH / 2 h / Heating 2: 5 N H2SO4 / 4.5 h / Heating
Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]
  • 6
  • [ 3446-89-7 ]
  • [ 144128-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 50percent aq. NaOH / 72 h / Ambient temperature 2: EtONa / ethanol / 6 h / Heating 3: 2 N NaOH / 2 h / Heating 4: 5 N H2SO4 / 4.5 h / Heating
Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]
  • 7
  • [ CAS Unavailable ]
  • [ 105-53-3 ]
  • [ 144128-74-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-Methylmercaptophenyl-3-buten-2-on; diethyl malonate With sodium ethanolate In ethanol for 12h; Stage #2: With sodium hydroxide In ethanol; water for 12h; Stage #3: With hydrogenchloride In diethyl ether; water 4.2. General procedure to prepare cyclohexane 1,3-dione (CHD) analogs7 General procedure: All aldehydes were previously prepared or purchased. Aldehyde 1 (5.0 mmol) was dissolved in THF (20 mL), and 1-(triphenylphosphoranylidene)-2-propanone (1.60 g, 5.0 mmol) was added. The mixture was allowed to stir at room temperature for 12 h. Solvent was removed under vacuum, and the residue was purified by flash column chromatography to provide 2, which was used directly in the next step, in almost quantitative yield.Compound 2 (2.0 mmol) and diethyl malonate (2.0 mmol) were dissolved in EtOH (5 mL), and a NaOEt solution (21 wt % in ethanol; 1.50 mL, 4.0 mmol) was added. After being stirred for 12 h, 3 N aq NaOH (20 mL) was added, and stirring was continued for another 12 h. Aqueous 3 N HCl was added until the solution turned cloudy. Ether was used to extract the cloudy mixture until the aqueous layer was clear. The combined organic portions were combined and allowed to stir for 4 h until decarboxylation was complete. Heating might be required in some cases when decarboxylation was not complete at room temperature. The solvent was evaporated, and the crude product was then purified by recrystallization or flash chromatography. The CHD product was typically a white solid, obtained in about an 80% yield, and had an Rf = 0.6 (dichloromethane/methanol = 8:1).
Reference： [1]Location in patent: experimental part Zhang, Wei; Benmohamed, Radhia; Arvanites, Anthony C.; Morimoto, Richard I.; Ferrante, Robert J.; Kirsch, Donald R.; Silverman, Richard B. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 1029 - 1045]
  • 8
  • [ 3446-89-7 ]
  • [ 144128-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 12 h / 20 °C 2.1: sodium ethanolate / ethanol / 12 h 2.2: 12 h
Reference： [1]Zhang, Wei; Benmohamed, Radhia; Arvanites, Anthony C.; Morimoto, Richard I.; Ferrante, Robert J.; Kirsch, Donald R.; Silverman, Richard B. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 1029 - 1045]

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