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[ CAS No. 138716-20-8 ]

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Product Details of [ 138716-20-8 ]

CAS No. :138716-20-8 MDL No. :MFCD00111509
Formula : C11H12FNO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :193.22 g/mol Pubchem ID :-
Synonyms :

Calculated chemistry of of [ 138716-20-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.18
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.44
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 2.07
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 2.09
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.668 mg/ml ; 0.00346 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 1.45 mg/ml ; 0.00749 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.286 mg/ml ; 0.00148 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 138716-20-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 138716-20-8 ]

* 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 [ 138716-20-8 ]

[ 138716-20-8 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 593-77-1 ]
  • [ 138716-20-8 ]
  • [ 143621-08-3 ]
YieldReaction ConditionsOperation in experiment
20% With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
  • 2
  • [ 26228-72-8 ]
  • [ 138716-20-8 ]
  • [ 143620-98-8 ]
YieldReaction ConditionsOperation in experiment
18% With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
  • 3
  • [ 403-42-9 ]
  • [ 4637-24-5 ]
  • [ 138716-20-8 ]
YieldReaction ConditionsOperation in experiment
97% In ethanol Reflux;
95% In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 48h; General experimental procedure for synthesis of Enaminones (5) General procedure: To a solution of acetophenone (1 mmol) in dry xylene (5 ml), was added a solution of DMF-DMA (2 mmol) and refluxed for 48h at 120°C. After cooling, the solvent was evaporated and residue was extracted with ethyl acetate (3x20ml). The combined organic layer was concentrated in vacuo and purified by recrystallisation with diethyl ether.
93% With <i>L</i>-proline In neat (no solvent) at 80℃; for 1h;
90% With guanidineacetic acid at 100℃; for 1h;
88% In toluene at 110℃; Inert atmosphere;
88% In toluene at 110℃;
88% In toluene at 110℃;
88% In toluene at 110℃; Inert atmosphere;
88% In toluene at 110℃;
76% In ethanol for 6h; Reflux; The acetophenone (25 mmol) was solved in ethanol (20 mL) and N,N-dimethylformamide dimethyl acetal (37 mmol) was added. The reaction mixture was stirred under reflux for 6 h and concentrated. The residue was elutriated in hexane and the remaining precipitate was filtered off, washed several times with hexane and dried.Intermediate B1: (E)-3-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one Yield: 76%1H-NMR (300 MHz, d6-DMSO): α=7.92 (m, 2H), 7.67 (d, 1H), 7.20 (m, 2H), 5.77 (d, 1H), 3.10 (bs, 3H), 2.87 (br s, 3H) ppm.
70% With boron trifluoride diethyl ether complex In toluene at 110℃; for 24h;
for 14h; Heating;
In N,N-dimethyl-formamide
at 120℃; for 16h;
In 5,5-dimethyl-1,3-cyclohexadiene Reflux; General procedure for synthesis of substituted (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one 2 (a-u) General procedure: To the appropriate methyl ketones 1 (a-u) (0.01 mol) in round-bottom flask, DMF-DMA (N,N-Dimethylformamide dimethyl acetal) was added and refluxed in xylene for the appropriate time. The solvent was evaporated in vacuum and the residual solid was crystallized from ethanol to afford corresponding pure product 2.
at 110℃; for 0.166667h; Microwave irradiation; 1 Synthesis of 1-(4-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one (3) To a solution of p-fluoroacetophenone (1) (10 mmol) in xylene or without solvent was added dimethylformamide-dimethylacetal (DMF-DMA) (12 mmol) and the mixture was mixed in a HP-500 Plus process vessel. The vessel was capped properly and irradiated by microwaves under pressurized conditions (17.2 bar, 110 °C) for 10 min. The excess DMF-DMA was evaporated in vacuo and the residue was dissolved in ether (50 mL) and dried over MgSO4. After evaporation of the solvent the resulting solid was recrystallized from hexane to afford (E)-1-(4-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one (2), The physical and spectral data of the synthesized compound are listed below. Mp.: 64-65 °C; IR (KBr) cm-1: 1664 (C=O), 1598 (C=N); 1H NMR (CDCl3): δ 3.02 (s, 6H, N(CH3)2), 5.67 (d, 1H, J = 12.3 Hz, -CO-CH]), 7.10 (d, 2H, Ar-H), 7.80 (d, J = 12.3 Hz, 1H, =CH-N), 7.92 (d, 2H, Ar-H).; MS (m/z): 193 (M+); C11H12FNO:Anal. Calcd: C, 68.38; H, 6.26; N, 7.25. Found C, 68.28; H, 6.16; N, 7.35. %.
In toluene at 110℃; Inert atmosphere;
In toluene at 110℃;
for 2h; Reflux; 41 A mixture of 1-(4-fluorophenyl)ethanone (2 g) and 1,1-dimethoxy-N,N-dimethylmethanamine (4 ml) was refluxed for 2 h. The solvent was removed. To the residue was added hexane to give the title compound as crystals (889 mg).1H-NMR (300 MHz, DMSO-d6) δ: 2.92 (3H, s), 3.14 (3H, s), 5.82 (1H, d, J=12.2 Hz), 7.24 (2H, m), 7.71 (1H, d, J=12.2 Hz), 7.96 (2H, dd, J=8.9, 5.7 Hz).
In 5,5-dimethyl-1,3-cyclohexadiene for 7h; Reflux; (1) Preparation of N,N-dimethylenaminones General procedure: The N,N-dimethylenaminones were synthesized according to literature method with slight modifications. 1 To a solution of ketones (1.54 g, 12.8 mmol) in xylene (15 mL) was added N,N-dimethylformamide dimethylacetal (3.6 mL, 25.7 mmol) and refluxed for 7 h (monitored by TLC). Xylene was then removed by distillation and crude residue was purified by column chromatography (silica gel; hexane-EtOAc = 3:7) to yield (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one ( 1 ) as a pure light yellow solid.
In acetonitrile at 82℃; for 1h; Microwave irradiation; Sealed tube; Synthesis of compounds 7a-m General procedure: A vial containing a mixture of aromatic ketone 13a-m (1 mmol) and N,N-dimethylformamide dimethyl acetal (12) (1 mmol) in CH3CN (3 mL) was sealed and placed in a Anton Paar Microwave Synthetic Reactor. The vial was subjected to microwave irradiation, programmed at 82 oC and 150W. After a period of 30 second, the temperature reached a plauteau, 82 oC, and remained constant. After stirring reaction for 60 min, 2-hydroxy-1,4-naphthoquinone (15) (1 mmol) and glacial AcOH (0.2 mmol) were added into the vial. The reaction was stirred for a further 30 min. The vial was then cooled to room temperature. Evaporation of the solvent gave crude products 7a-m, which was purified by column chromatography using a MeOH-EtOAc-DCM eluent (1:4:5)

Reference: [1]Al-Romaizan, Abeer N.; Ahmed, Nesreen S.; Elfeky, Sherin M. [Journal of Chemistry, 2019, vol. 2019]
[2]Prajapti, Santosh Kumar; Nagarsenkar, Atulya; Guggilapu, Sravanthi Devi; Gupta, Keshav Kumar; Allakonda, Lingesh; Jeengar, Manish Kumar; Naidu; Babu, Bathini Nagendra [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3024 - 3028]
[3]Kumar, Dinesh; Kommi, Damodara N.; Chopra, Pradeep; Ansari, Md Imam; Chakraborti, Asit K. [European Journal of Organic Chemistry, 2012, # 32, p. 6407 - 6413,7]
[4]Location in patent: experimental part Bindal, Sachin; Kumar, Dinesh; Kommi, Damodara N.; Bhatiya, Sonam; Chakraborti, Asit K. [Synthesis, 2011, # 12, p. 1930 - 1935]
[5]Jiang, Yaojia; Liang, Gaohui; Zhang, Cong; Loh, Teck-Peng [European Journal of Organic Chemistry, 2016, vol. 2016, # 20, p. 3326 - 3330]
[6]Ni, Meiyan; Zhang, Jianguo; Liang, Xiaoyu; Jiang, Yaojia; Loh, Teck-Peng [Chemical Communications, 2017, vol. 53, # 91, p. 12286 - 12289]
[7]Wang, Fei; Sun, Wangbing; Wang, Yixin; Jiang, Yaojia; Loh, Teck-Peng [Organic Letters, 2018, vol. 20, # 4, p. 1256 - 1260] Liang, Gaohui; Rong, Jiaxin; Sun, Wangbin; Chen, Gengjia; Jiang, Yaojia; Loh, Teck-Peng [Organic Letters, 2018] Liang, Gaohui; Rong, Jiaxin; Sun, Wangbin; Chen, Gengjia; Jiang, Yaojia; Loh, Teck-Peng [Organic Letters, 2018, vol. 20, # 22, p. 7326 - 7331]
[8]Liang, Xiaoyu; Guo, Pan; Yang, Wenjie; Li, Meng; Jiang, Chengzhou; Sun, Wangbin; Loh, Teck-Peng; Jiang, Yaojia [Chemical Communications, 2020, vol. 56, # 13, p. 2043 - 2046]
[9]Wang, Fei; Fu, Rui; Chen, Jie; Rong, Jiaxin; Wang, Enfu; Zhang, Jian; Zhang, Zhengyu; Jiang, Yaojia [Chemical Communications, 2022, vol. 58, # 21, p. 3477 - 3480]
[10]Current Patent Assignee: BAYER AG - US2012/237446, 2012, A1 Location in patent: Page/Page column 14
[11]Rosa, Fernanda A.; Machado, Pablo; Bonacorso, Helio G.; Zanatta, Nilo; Martins, Marcos A. P. [Journal of Heterocyclic Chemistry, 2008, vol. 45, # 3, p. 879 - 885]
[12]Wright, Stephen W.; Harris, Richard R.; Kerr, Janet S.; Green, Alicia M.; Pinto, Donald J.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4061 - 4068]
[13]Clough, Stuart; Gupton, John; Ligali, Adepeju; Roberts, Matthew; Driscoll, David; Annett, Scott; Hewitt, Alisa; Hudson, Matthew; Jackson, Edward; Miller, Robert; Norwood, Bradley; Kanters, Rene; Wyre, Hadley; Petruzzi, Heather [Tetrahedron, 2005, vol. 61, # 31, p. 7554 - 7561]
[14]Yang, Hua-Lin; Fang, Fei; Zhao, Chang-Po; Li, Dong-Dong; Li, Jing-Ran; Sun, Jian; Du, Qian-Ru; Zhu, Hai-Liang [MedChemComm, 2014, vol. 5, # 2, p. 219 - 225]
[15]Deng, Chang-Bo; Li, Juan; Li, Lu-Yi; Sun, Feng-Jie [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3195 - 3201]
[16]Althagafi, Ismail I.; Shaaban, Mohamed R. [Journal of Molecular Structure, 2017, vol. 1142, p. 122 - 129]
[17]Shi, Pengfei; Wang, Lili; Chen, Kehao; Wang, Jie; Zhu, Jin [Organic Letters, 2017, vol. 19, # 9, p. 2418 - 2421]
[18]Song, Chao; Yang, Chen; Zeng, Hua; Zhang, Wenjing; Guo, Shan; Zhu, Jin [Organic Letters, 2018, vol. 20, # 13, p. 3819 - 3823]
[19]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2010/94000, 2010, A1 Location in patent: Page/Page column 28
[20]Tang, Yucai; Chen, Ying; Liu, Hui; Guo, Min [Tetrahedron Letters, 2018, vol. 59, # 41, p. 3703 - 3705]
[21]Nguyen, Ha-Thanh; Dang Thi, Tuyet Anh; Hoang Thi, Phuong; Le-Nhat-Thuy, Giang; Nguyen Thi, Quynh Giang; Nguyen Tuan, Anh; Le Thi, Tu Anh; Van Nguyen, Tuyen [Tetrahedron Letters, 2021, vol. 81]
  • 4
  • [ 622-30-0 ]
  • [ 138716-20-8 ]
  • [ 143621-09-4 ]
YieldReaction ConditionsOperation in experiment
34% With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
  • 5
  • [ 138716-20-8 ]
  • ethyl 2-(phenoxysulfonyl)ethanimidoate hydrochloride [ No CAS ]
  • phenyl 2-amino-6-(4-fluorophenyl)pyridine-3-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With ammonium acetate In ethanol for 4h; Heating;
  • 6
  • [ 141-97-9 ]
  • [ 138716-20-8 ]
  • [ 31676-67-2 ]
YieldReaction ConditionsOperation in experiment
93% With gallium(III) iodide; ammonium acetate In neat (no solvent) at 80℃; for 1h;
82% With anhydrous ammonium acetate; Montmorillonite K10 In isopropanol Heating;
With ammonium acetate; glacial acetic acid Reflux; General procedure for synthesis of ethyl 2-methyl-6- substituted phenylnicotinate 3 (a-u) General procedure: To a above synthesized solution of the appropriate enaminone 2 (a-u) (1 mmol) in glacial acetic acid (15 mL), ethyl acetoacetate (1.5 mmol) and ammonium acetate (40 mmol) were added. The reaction mixture was heated under reflux for 5-8 h. After cooling and pouring into ice-water, the residue obtained was filtered and washed with petroleum ether then with water and finally crystallized from ethanol to yield the desired product 3 (a-u).
  • 7
  • [ 138716-20-8 ]
  • [ 161891-29-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (E)-3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one With trichlorophosphate Stage #2: With water In tetrahydrofuran
  • 8
  • [ 138716-20-8 ]
  • [ 16617-46-2 ]
  • 3-cyano-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.64% In acetic acid at 120℃; for 0.333333h; microwave irradiation;
  • 9
  • [ 138716-20-8 ]
  • [ 6994-25-8 ]
  • ethyl 7-(4-fluoroxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.56% In acetic acid at 120℃; for 0.333333h; microwave irradiation;
  • 10
  • [ 138716-20-8 ]
  • 3,4,5-trimethoxyphenylguanidinium nitrate [ No CAS ]
  • [4-(4-fluoro-phenyl)-pyrimidin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; for 1h;
  • 11
  • [ 138716-20-8 ]
  • N-(3-methoxyphenyl)guanidine nitrate [ No CAS ]
  • [4-(4-fluoro-phenyl)-pyrimidin-2-yl]-(3-methoxy-phenyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; for 1h;
  • 12
  • [ 138716-20-8 ]
  • 1,3-di-(4-morpholinyl)-1-(p-fluorophenyl)-2-propenylium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: POCl3 1.2: H2O / tetrahydrofuran 2.1: acetonitrile / 20 °C 2.2: 80 percent / NaPF6 / methanol
  • 13
  • [ 138716-20-8 ]
  • [ 149839-50-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 34 percent / p-TsOH / methanol / 0.5 h / 20 °C 2: 44 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
  • 14
  • [ 108-98-5 ]
  • [ 138716-20-8 ]
  • [ 102360-62-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; sodium cyanoborohydride; trichlorophosphate In diethyl ether; chloroform; isopropyl alcohol 40 EXAMPLE 40 EXAMPLE 40 By using a method similar to that described in Example 35, but starting from 1-(4-fluorophenyl)-3-dimethylamino-2-propen-1-one (10 g), phosphorus oxychloride (4.76 cc), thiophenol (5.57 cc) and sodium cyanoborohydride (1.92 g), a residue is obtained which is taken up in chloroform. The solution is then adjusted to pH 10 by adding a concentrated aqueous solution of sodium hydroxide. The organic phase is separated and then the aqueous phase is extracted with methylene chloride. The organic phases are collected, dried over sodium sulphate, filtered and then evaporated to dryness under reduced pressure (2.7 kPa) at 30° C. A residue is obtained which is dissolved in isopropanol (30 cc). A 3N solution (12 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The solid which precipitates is separated off by filtration and recrystallized from isopropanol (30 cc). In this way 1-dimethylamino-3-(4-fluorophenyl)-3-phenylthio-2-propene (E) hydrochloride (3.3 g) is obtained in the form of a white solid melting at 160° C. 1-(4-Fluorophenyl)-3-dimethylamino-2-propen-1-one can be obtained by using the method described by H. Meerwein, W. Florian, N. Schon and G. Stopp, Ann. Chem. 641, 1, (1961).
  • 15
  • [ 403-42-9 ]
  • [ 138716-20-8 ]
YieldReaction ConditionsOperation in experiment
With <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal In hexane 48 3-Dimethylamino-4'-fluoroacrylophenone EXAMPLE 48 3-Dimethylamino-4'-fluoroacrylophenone A mixture of 5.0 g. of p-fluoroacetophenone and 10 ml. of dimethylformamide dimethylacetal is refluxed for 4 hours. Evaporation gives an oil which crystallizes with the addition of hexane to give the product, m.p. 83.5°-84° C.
  • 18
  • [ 4755-77-5 ]
  • [ 138716-20-8 ]
  • [ 1010796-75-4 ]
YieldReaction ConditionsOperation in experiment
76% With pyridine In dichloromethane at 40℃; for 15h;
  • 19
  • [ 138716-20-8 ]
  • [ 407-25-0 ]
  • [ 1010796-76-5 ]
YieldReaction ConditionsOperation in experiment
80% With pyridine In dichloromethane at 40℃; for 15h;
  • 20
  • [ 138716-20-8 ]
  • [ 138716-37-7 ]
  • [ 651059-64-2 ]
YieldReaction ConditionsOperation in experiment
1: 9% 2: 54% With pyridine; hydroxylamine hydrochloride In ethanol at 78℃; for 16h;
  • 21
  • [ 138716-20-8 ]
  • [ 60-34-4 ]
  • [ 689251-78-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol for 4h; Reflux; 42 A mixture of (2E)-3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one (800 mg) and methylhydrazine (257 μl) in ethanol was refluxed for 4 h. The solvent was removed, and the residue was chromatographed on basic silica gel using hexane/ethyl acetate as an eluent to give the title compound (592 mg).1H-NMR (300 MHz, DMSO-d6) δ: 3.83 (3H, s), 6.39 (1H, d, J=1.9 Hz), 7.34 (2H, dd), 7.46 (1H, d, J=1.5 Hz), 7.58 (2H, dd, J=8.9, 5.5 Hz).
  • 22
  • [ 138716-20-8 ]
  • [ 1346269-43-9 ]
YieldReaction ConditionsOperation in experiment
97% With Tris(trimethylsilyl)phosphane; cesium fluoride In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
  • 23
  • [ 138716-20-8 ]
  • [ 17154-34-6 ]
  • (E)-[4-((3'-N,N-dimethylamino)prop-2'-en-1'-onyl)phenyl]diphenylphosphine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With cesium fluoride In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere;
  • 24
  • [ 138716-20-8 ]
  • [ 1491142-18-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C
  • 25
  • [ 138716-20-8 ]
  • [ 1491142-21-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C
  • 26
  • [ 138716-20-8 ]
  • [ 1491142-25-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice
  • 27
  • [ 138716-20-8 ]
  • [ 1491142-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice
  • 28
  • [ 138716-20-8 ]
  • [ 1491142-32-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice
  • 29
  • [ 138716-20-8 ]
  • [ 1491142-36-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice
  • 30
  • [ 138716-20-8 ]
  • C11H6ClFN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux
  • 31
  • [ 3473-63-0 ]
  • [ 138716-20-8 ]
  • [ 68049-19-4 ]
YieldReaction ConditionsOperation in experiment
66% With sodium ethanolate In ethanol at 70℃; 5.4. General procedure for the preparation of 4-substititedphenylpyrimidines (21a-d) General procedure: To the mixture of formamidine acetate (9.9g, 0.096mol), sodium ethoxide (10.9g, 0.16mol) and anhydrous EtOH (300mL), an appropriate (E)-3-(dimethylamino)-1-substititedphenylprop-2-en-1-one (0.08mol) was added slowly at 70°C. Upon the completion of addition, the reaction mixture then was stirred at reflux for 15-20h and monitored by TLC. The solvent was concentrated in vacuum and the residue was resolved with dichloromethane (300mL), washed with water (30mL×3), brine (60mL), dried over anhydrous Na2SO4, and concentrated in vacuum to give the corresponding 4-substititedphenylpyrimidines as light yellow solids.
  • 32
  • [ 403-42-9 ]
  • [ 33513-42-7 ]
  • [ 138716-20-8 ]
YieldReaction ConditionsOperation in experiment
86% In N,N-dimethyl acetamide; toluene at 110℃; Inert atmosphere;
84% In dimethyl amine at 80℃; 5.4.General procedure for the preparation of (E)-3-(dimethylamino)-1-substititedphenylprop-2-en-1-ones (20a-d) General procedure: A mixture of an appropriate substituted acetophenone (0.1mol) and DMF-DMA (39.8mL, 0.3mol) was heated at 80°C for 8-12h and monitored by TLC. Upon cooling to room temperature of the reaction mixture, Et2O (40mL) and petroleum ether (120mL) were added and stirred for 0.5h, and then the precipitatewas collected by filtration and dried to give the corresponding (E)-3-(dimethylamino)-1-substititedphenylprop-2-en-1-one as yellow solids.
71% With 1,1-dimethoxyethane In toluene for 4h; Reflux; 342.2 Step 2. Synthesis of (2E)-3-(Dimethylamino)-1-(4-fluorophenyl)-2-propen-1-one Step 2. Synthesis of (2E)-3-(Dimethylamino)-1-(4-fluorophenyl)-2-propen-1-one A solution of 1-(4-fluorophenyl)ethanone (0.875 mL, 7.24 mmol) in toluene (5.0 mL) and N,N-dimethylformamide dimethyl acetal (DIFDA, 1.35 mL, 10.1 mmol) were used to carry out the reaction. After the reaction was reflux for 4 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-60% ethyl acetate in n-hexane) to give (2E)-3-(dimethylamino)-1-(4-fluorophenyl)-2-propen-1-one (0.987 g, 71%). 1H NMR (CDCl3, 400 MHz) δ 7.91 (dd, 2H), 7.80 (d, 1H), 7.07 (dd, 2H), 5.67 (d, 1H), 3.15 (br s, 3H), 2.93 (br s, 3H).
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