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[ CAS No. 5739-37-7 ] {[proInfo.proName]}

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Chemical Structure| 5739-37-7
Chemical Structure| 5739-37-7
Structure of 5739-37-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5739-37-7 ]

CAS No. :5739-37-7 MDL No. :MFCD03842928
Formula : C15H13ClO Boiling Point : -
Linear Structure Formula :- InChI Key :GQNOPFDKLUGQEC-UHFFFAOYSA-N
M.W : 244.72 Pubchem ID :247344
Synonyms :

Calculated chemistry of [ 5739-37-7 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 70.94
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : 4.12
Log Po/w (WLOGP) : 4.16
Log Po/w (MLOGP) : 4.03
Log Po/w (SILICOS-IT) : 4.75
Consensus Log Po/w : 3.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.21
Solubility : 0.015 mg/ml ; 0.0000615 mol/l
Class : Moderately soluble
Log S (Ali) : -4.18
Solubility : 0.016 mg/ml ; 0.0000653 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.29
Solubility : 0.000124 mg/ml ; 0.000000508 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.55

Safety of [ 5739-37-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5739-37-7 ]

* 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 [ 5739-37-7 ]

[ 5739-37-7 ] Synthesis Path-Downstream   1~70

  • 1
  • [ 776297-03-1 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide
  • 2
  • [ 99-91-2 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
97% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; 2-(2-(diphenylphosphanyl)phenyl)benzo[d]oxazole; potassium hydroxide In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere; 4.3. General procedure for alkylation reactions General procedure: [Cp*IrCl2]2 (1 mol %, 0.01 mmol, 8.0 mg), 4a (2 mol %, 0.02 mmol,7.6 mg), KOH (10 mol %, 0.1 mmol, 5.6 mg), and toluene (5 mL) wereadded to a 25mL Schlenk tube with stirring under N2 at roomtemperature. Then ketones/secondary alcohols/amines (1 mmol),primary alcohols (1.1 mmol) were added by syringe. The reactionmixture was heated to 110 °C under reflux in an oil bath for 24 h. Itwas cooled to ambient temperature. Then it was concentrated invacuo, and purified by flash column chromatography with petroleumether/ethyl acetate to afford the corresponding alkylatedproduct.
95% With potassium carbonate at 135℃; for 12h;
95% With lithium tert-butylate In toluene at 110℃; for 12h; Inert atmosphere;
95% With titanium(IV) dioxide; potassium hydroxide In toluene at 100℃; for 10h; Sealed tube; Irradiation;
92% With [Ru(η6-p-cymene)Cl2]2; Cs2CO3; 2-((diphenylphosphino)amido)pyridine In toluene at 120℃; for 18h; Schlenk technique; Inert atmosphere; General procedure for the [RuCl26-p-cymene)]2/L1-catalyzed α-alkylation of ketones with alcohols General procedure: Cs2CO3 (0.6 mmol,195.6 mg) and toluene (1 mL) were added to a Schlenk tube under a N2 atmosphere. [RuCl2(η6-p-cymene)]2 (0.005 mmol, 3.1 mg), L1 (0.01 mmol, 2.8 mg), alcohols (1.1 mmol) and ketones (1.0 mmol) were added in that order and the Schlenk tube was closed and stirred at 120°C for 18 h. The reaction mixture was cooled to room temperature, quenched with water and extracted with ethyl acetate (20 mL x 3). The combined extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by column chromatography using petroleum ether/ethyl acetate as eluent to give the corresponding product (Figs. S22-S47 in Supporting Information).
91% With C31H36ClN4Ru(1+)*F6P(1-); potassium hydroxide In toluene at 120℃;
90% With C16H14IrN2O3; Cs2CO3 In tert-Amyl alcohol for 6h; Reflux; 23 1-(4-chlorophenyl)-3-phenylpropan-1-one 4- chloroacetophenone (155mg, 1mmol), cat.1 (5.4mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), benzyl alcohol (120mg, 1.1mmol) and tert-amyl alcohol (1ml) were sequentially added to a 5mL round bottomed flask.After the reaction mixture was refluxed in air for six hours, cooled to room temperature. The solvent is removed by rotary evaporation, then purified by column chromatography (developingOpen solvent: petroleum ether / ethyl acetate) to give the pure title compound Yield: 90%
90% With [{CyPN(H)P}Co(CH2SiMe3)]-BArF4; potassium-t-butoxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;
89% With C38H43ClIrN2O2P; Cs2CO3; silver(I) bis(trifluoromethanesulfonyl)imide In toluene at 120℃; for 16h;
89% With potassium-t-butoxide; C35H33Cl2CoN5O2 In toluene at 110℃; for 24h; Inert atmosphere;
89% With [Ru(P(Ph){(o-C6H4)(1,2,3-N3C(Ph)CH)}2)(Cl)(PPh3)(H2O)]Cl; potassium hydroxide In 1,4-dioxane at 120℃; for 12h; Inert atmosphere;
87% With (S)-methyl 2-(2-(1H-benzo[d][1,2,3]triazol-1-yl)acetamido)propanoate; sodium tertiary butoxide In toluene at 110℃; for 48h; Schlenk technique; Inert atmosphere;
86% With C27H24Cl3F6IrN2; potassium hydroxide In toluene at 130℃; for 2h;
86% With dichloro[1,3‐diethyl(5,6‐dimethyl)benzimidazolin‐2‐ylidene](benzene)ruthenium (II); sodium hydroxide In toluene at 105℃; for 8h;
84% With bis(μ-chloro)-bis[1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C(2'),N-iridium chloride]; Cs2CO3 In tert-Amyl alcohol for 12h; Reflux;
84% With C38H36Cl4Ir2N4; Cs2CO3 In tert-Amyl alcohol for 12h; Reflux; 18 Example 18: 1-(4-chlorophenyl)-3-phenylpropan-1-one 4-Chloroacetophenone (78 mg, 0.5 mmol),Cat. [Ir] (5.4 mg, 0.005 mmol, 1.0 mol%),Cesium carbonate (33 mg, 0.1 mmol, 0.2 equiv.),Benzyl alcohol (65 mg, 0.6 mmol)And tert-amyl alcohol (1 ml) were successively added to a 5 mL round bottom flask.The reaction mixture was refluxed in air for 12 hours,Cool to room temperature.Rotate the solvent to remove the solvent,The purified title compound was then purified by column chromatography (developing solvent: petroleum ether / ethyl acetate)Yield: 84%
84% With potassium fluoride; N,N,N-tributylbutan-1-aminium fluoride; isopropanol; silver(I) bis(trifluoromethanesulfonyl)imide In lithium hydroxide monohydrate at 90℃; for 48h; Inert atmosphere; Typical procedure for 8a General procedure: Acetophenone (120 mg), benzyl alcohol (128.7 mg), AgNTf2 (116 mg), KF (17.4 mg), TBAF (74 mg), iPrOH (180 mg) and TPT-ZnMS (10 mg) were added to a reaction tube under nitrogen atmosphere. Water (3.5 mL) and a stir bar were added to the reaction tube, and stirred for 48 h in 90 oC under nitrogen atmosphere.
82% With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); Cs2CO3 In tert-Amyl alcohol for 6h; Reflux;
82% With sodium tertiary butoxide In toluene at 120℃; for 8h;
78% With samarium diiodide; potassium-t-butoxide In tetrahydrofuran; toluene at 140℃; for 1h; Microwave irradiation; Inert atmosphere;
76% With C52H43Cl2IrN2P2; sodium hydroxide In 1,4-dioxane at 110℃; for 12h; Inert atmosphere; 4.4. General procedure for α-alkylation of ketones with alcohols General procedure: To a solution of Ir(III) complex (0.02 mmol) and base (1.0 mmol) in solution (3 mL) was added the corresponding ketone (1.0 mmol) and alcohol (2.0 mmol) under nitrogen. The reaction mixture was then placed in an oil bath and heated at 110 °C for 12 h, cooled and quenched with water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate, then the combined organic layers were washed with water, dried over MgSO4, filtered, and the solvent was removed on a rotary evaporator. The resulting residue was purified by flash chromatography on silica gel using suitable mixtures of hexane/ethyl acetate as eluent. The products were characterized by comparing their m.p., IR and 1 H NMR spectra with those found in the literature [8], [12], [15], [32] and [33].
74% With bis(triphenylphosphine)(carbonyl)rhodium chloride; potassium hydroxide In 1,4-dioxane at 95℃; for 9h; chemoselective reaction; General procedure for the synthesis of alkylated ketones General procedure: Ketones (1 mmol), alcohols (1.5 mmol), RhCl(CO)(PPh3)2 (2 mol%) and bases (2mmol) were added into dioxane (3 mL). The reaction mixture was stirred at 95 forcompletion monitored by TLC. Then the solution was filtered by suction and the solventwas evaporated under reduced pressure. The residue was passed through flash columnchromatography on silica gel to give the pure products.
74% With potassium phosphate tribasic trihydrate; C39H32Cl2N5PRu In tert-Amyl alcohol at 120℃; for 4h; Inert atmosphere; Schlenk technique;
74% With dimanganese decacarbonyl; sodium hydroxide In toluene at 110℃; for 2h; Inert atmosphere; Glovebox; Sealed tube;
67% With [(Cp*IrCl)2(thbpym)][Cl]2; potassium hydroxide In lithium hydroxide monohydrate at 100℃; for 12h; Green chemistry;
67% With [(Cp*IrCl)2(thbpym)][Cl]2; potassium hydroxide In lithium hydroxide monohydrate for 12h; Reflux; 22 Example 22: 3-phenyl-1-(4-chlorophenyl)-1-acetone Benzyl alcohol (54mg, 0.5mmol), p-chloroacetophenone (100.5mg, 0.65mmol), [(Cp*IrCl)2(thbpym)][Cl]2(2.5mg, 0.0025mmol, 1mol Ir%),Potassium hydroxide (28mg, 0.5mmol, 1 equiv) and water (1mL) were sequentially added to a 5mL round bottom flask. The reaction mixture was refluxed in air for 12 hours and then cooled to room temperature.The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate), yield: 67%.
62% With 1,10-Phenanthroline; potassium-t-butoxide; nickel(II) bromide In toluene at 140℃; for 36h; Schlenk technique; Inert atmosphere;
51% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; N-hexadecyl-N,N,N-trimethylammonium bromide; potassium hydroxide In tetrahydrofuran; lithium hydroxide monohydrate at 40℃; for 20h; Inert atmosphere; Schlenk technique;
With lithium benzyloxide
15 %Spectr. With tripotassium phosphate tribasic In neat (no solvent) at 175℃; for 24h; Sealed tube;
77 %Spectr. With chloro(η5-pentamethylcyclopentadienyl)(η2-pyridine-2-carboxylato)iridium(III); potassium hydroxide In toluene at 120℃; for 2h; 4.4 General procedure for the alpha alkylation of ketones with alcohols General procedure: The reaction was carried out in Radleys Carousel 12 Plus Reaction Station. The substrates (ketone (1.0mmol)/alcohol (1.0mmol)), catalyst (0.002mmol), KOH (0.2mmol), and 1,3,5-trimethoxybenzene (used as an internal standard) were combined in an oven-dried Radleys tube. Toluene (1.0ml) was added to the tube, and the mixture was refluxed under air for 2h at 120°C. The reaction was cooled and diluted with EtOAc, and the reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was analyzed by 1H NMR.
With potassium-t-butoxide In toluene at 125℃; for 24h; Schlenk technique;

Reference: [1]Huang, Shuang; Wu, Si-Peng; Zhou, Quan; Cui, He-Zhen; Hong, Xi; Lin, Yue-Jian; Hou, Xiu-Feng [Journal of Organometallic Chemistry, 2018, vol. 868, p. 14 - 23]
[2]Cui, Xinjiang; Zhang, Yan; Shi, Feng; Deng, Youquan [Chemistry - A European Journal, 2011, vol. 17, # 3, p. 1021 - 1028]
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  • 3
  • [ 25186-51-0 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) at 75℃;
In hexane at 20 - 23℃; Irradiation;
  • 4
  • [ 3277-89-2 ]
  • [ 16090-16-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
With dichlorotriphenylphosphorane 1.) CH2Cl2, THF, -30 deg C, 1 h; 2.) THF, 1 h; Yield given. Multistep reaction;
  • 5
  • [ 5739-37-7 ]
  • [ 59749-78-9 ]
YieldReaction ConditionsOperation in experiment
84% With trifluorormethanesulfonic acid at 80℃; for 18h;
77% With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; Schlenk technique;
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 12 h / 50 °C / Schlenk technique; Inert atmosphere
  • 6
  • [ 5739-37-7 ]
  • [ 63635-59-6 ]
YieldReaction ConditionsOperation in experiment
Huang-Minlon reduction;
  • 7
  • [ 5739-37-7 ]
  • [ 60851-30-1 ]
YieldReaction ConditionsOperation in experiment
85% With bromine In acetic acid at 50℃;
  • 8
  • [ 6948-70-5 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
74% With dichromate anion
  • 9
  • [ 956-02-5 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
99% With 10% Pd/C; diphenyl sulfide; hydrogen In methanol at 20℃; for 24h; chemoselective reaction;
98% With selenium; carbon monoxide; water In N,N-dimethyl-formamide at 90℃; for 2h;
98% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium carbonate; isopropyl alcohol at 85℃; for 5h; Inert atmosphere; Schlenk technique; chemoselective reaction;
97% With formic acid In toluene at 120℃; for 20h; Inert atmosphere; chemoselective reaction;
97% With hydrogen; tetra-(n-butyl)ammonium iodide In water at 110℃; for 24h; chemoselective reaction;
96% With diammonium phosphate; manganese(II) sulfate; dipotassium hydrogenphosphate; Hexadecane; Corynebacterium equi IFO 3730; magnesium sulfate; iron(II) sulfate; zinc(II) sulfate In water at 30℃; for 72h;
96% With Corynebacterium equii IFO 3730 In various solvent(s) at 30℃; for 72h;
96% With hydrogen In ethanol; water at 25℃; for 12h; chemoselective reaction;
96% With ethanol; caesium carbonate; bis(pinacol)diborane at 110℃; for 0.666667h; Microwave irradiation; Sealed tube; Green chemistry; chemoselective reaction;
96% With hydrogen In methanol at 20℃; for 5h; chemoselective reaction;
94% With Cu6(2-benzothiazolethiol(1-))6; potassium carbonate; butan-1-ol In butan-1-ol at 120℃; for 24h; Inert atmosphere; chemoselective reaction;
91% With acetoxy(2,6-bis((diphenylphosphino)methyl)-3,5-dimethylphenyl)palladium(II); potassium carbonate; butan-1-ol for 1h; Reflux; chemoselective reaction;
90% With hydrogen In ethanol at 20℃; for 5h; Green chemistry;
86% With formic acid In toluene at 97℃; for 8h;
85% With methanol; ammonium chloride In dimethyl sulfoxide at 20℃; for 6h; Electrochemical reaction; chemoselective reaction;
83% With ammonium formate In acetonitrile at 80℃; for 7h;
82% With sodium hydrogen selenide In ethanol at 50℃; for 3h;
81% With 10% Pd on charcoal; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In ethanol for 8h; Reflux;
79% Stage #1: 4'-chlorochalcone With magnesium(II) perchlorate; 1,3-Dimethyl-2,3-dihydro-1H-benzoimidazole In toluene at 80℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene for 0.166667h; Irradiation; 4.4. General procedure for reduction of α,β-unsaturated ketones General procedure: A solution of the α,β-unsaturated ketone (0.5 mmol) and DMBI (0.5-1.0 mmol) or o-phenylenediamine (0.5 mmol) and benzaldehyde (0.5 mmol) or PBT (0.5-1.5 mmol) in benzene (7 mL) or toluene (7 mL) in the presence of a Lewis acid (5-20 mol %) was stirred in a Schlenk tubes at 25-80 °C for 12-48 h under an argon atmosphere. The reaction was monitored by TLC. After completion of the reaction, 1 mL HCl (0.1 mol/L) was added to the solution and stirred for 10 min, and then the resulted aqueous mixture was concentrated under reduced pressure and the residue followed by column chromatography on silica gel and the obtained corresponding saturated ketones were identified by 1H and 13C NMR.
63% With indium; isopropyl alcohol; cobalt(II) iodide; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 80℃; for 24h; Glovebox; Inert atmosphere; Green chemistry; chemoselective reaction;
57% With triethylsilane; 1,1,1,3',3',3'-hexafluoro-propanol; tris(pentafluorophenyl)borate at 40℃; for 1h; chemoselective reaction;
With formic acid In toluene at 97℃; for 8h;
With Wilkinson's catalyst; ammonium formate at 90℃; for 0.25h; Ionic liquid; chemoselective reaction;
With ammonium formate In toluene at 90℃; for 12h; chemoselective reaction; 2.3 General Procedure of Chemoselective Transfer Hydrogenation of α,β-Unsaturated Carbonyl Compounds General procedure: The round bottom flask containing a,b-unsaturated carbonyl (1 mmol), HCOONH4 (3 mmol) and ImmPd-IL (2 mol %) was added toluene (10 ml) and reaction mixture heated at 90 °C for 12 h. The progress of the reaction was monitored by using TLC and GC analysis. After completion,the reaction mixture was cooled to room temperature and then filtered to separate catalyst. The filtrate was then evaporated under high vacuum and obtained residue waspurified by column chromatography using silica gel (100-200 mesh size) with pet ether and ethyl acetate (95:5) to give the desired pure product.
90 %Chromat. With hydrogen In ethanol; water at 80℃; for 1.75h;

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[8]Morimoto, Naoki; Yamamoto, Shun-Ichi; Takeuchi, Yasuo; Nishina, Yuta [RSC Advances, 2013, vol. 3, # 36, p. 15608 - 15612]
[9]Huang, Xi; Hu, Junjie; Wu, Mengying; Wang, Jiayi; Peng, Yanqing; Song, Gonghua [Green Chemistry, 2018, vol. 20, # 1, p. 255 - 260]
[10]Patel, Heta A.; Rawat, Maitreyee; Patel, Arun L.; Bedekar, Ashutosh V. [Applied Organometallic Chemistry, 2019, vol. 33, # 4]
[11]Zhang, Meng-Juan; Tan, Da-Wei; Li, Hong-Xi; Young, David James; Wang, Hui-Fang; Li, Hai-Yan; Lang, Jian-Ping [Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1204 - 1215]
[12]Ding, Boqiang; Zhang, Zhenfeng; Liu, Yangang; Sugiya, Masashi; Imamoto, Tsuneo; Zhang, Wanbin [Organic Letters, 2013, vol. 15, # 14, p. 3690 - 3693]
[13]Nasrollahzadeh, Mahmoud [New Journal of Chemistry, 2014, vol. 38, # 11, p. 5544 - 5550]
[14]Azran, Jacques; Buchman, Ouri; Orchin, Milton; Blum, Jochanan [Journal of Organic Chemistry, 1984, vol. 49, p. 1327 - 1333]
[15]Huang, Binbin; Li, Yanan; Yang, Chao; Xia, Wujiong [Chemical Communications, 2019, vol. 55, # 47, p. 6731 - 6734]
[16]Chambyal, Omkar Singh; Paul, Satya; Shamim, Tahira; Gupta, Monika; Gupta, Rajive; Loupy, Andre [Synthetic Communications, 2013, vol. 43, # 5, p. 656 - 667]
[17]Nishiyama, Yutaka; Yoshida, Masanori; Ohkawa, Shigeo; Hamanaka, Sawako [Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6720 - 6722]
[18]Location in patent: scheme or table Liu, Qiang; Li, Jing; Shen, Xiao-Xia; Xing, Rui-Guang; Yang, Jie; Liu, Zhengang; Zhou, Bo [Tetrahedron Letters, 2009, vol. 50, # 9, p. 1026 - 1028]
[19]Location in patent: experimental part Feng, Yi-Si; Yang, Chun-Yan; Huang, Qiang; Xu, Hua-Jian [Tetrahedron, 2012, vol. 68, # 25, p. 5053 - 5059]
[20]Jiang, Biao-Lin; Ma, Shuang-Shuang; Wang, Meng-Liang; Liu, Dian-Sheng; Xu, Bao-Hua; Zhang, Suo-Jiang [ChemCatChem, 2019, vol. 11, # 6, p. 1701 - 1706]
[21]Zhan, Xiao-Yu; Zhang, Hua; Dong, Yu; Yang, Jian; He, Shuai; Shi, Zhi-Chuan; Tang, Lei; Wang, Ji-Yu [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6578 - 6592]
[22]Azran, Jacques; Buchman, Ouri; Blum, Jochanan [Tetrahedron Letters, 1981, vol. 22, # 20, p. 1925 - 1928]
[23]Location in patent: scheme or table Baan, Zoltan; Finta, Zoltan; Keglevich, Gyoergy; Hermecz, Istvan [Green Chemistry, 2009, vol. 11, # 12, p. 1937 - 1940]
[24]Patil, Nilesh M.; Sasaki, Takehiko; Bhanage, Bhalchandra M. [Catalysis Letters, 2014, vol. 144, # 11, p. 1803 - 1809]
[25]Sharma, Sukanya; Sharma, Chandan; Kaur, Manpreet; Paul, Satya [New Journal of Chemistry, 2021, vol. 45, # 43, p. 20309 - 20322]
  • 10
  • [ 3277-89-2 ]
  • [ 74-11-3 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene 1.) THF, dichloromethane, 0 deg C, 3 h; 2.) 0 deg C, 1 h; Yield given. Multistep reaction;
YieldReaction ConditionsOperation in experiment
Rk. m. Morpholin, Schwefel, 3h, 130grad, -> partielle Umlagerung (25percent) in ω-(4-Chlor-benzyl)-acetophenon;
YieldReaction ConditionsOperation in experiment
Entspr. Chalkon, Hydrierung;
Polymergebundene 3-Phenylpropionsaeure, p-Chlorbenzoesaeure, Esterkondensation;
α,β-ungesaett. Keton, Katal. H2-Transfer;
4-Chlor-ω-benzyliden-acetophenon, katalyt. Hydrierung;
ω-(4-Chlor-benzyl)-acetophenon, Morpholin, Schwefel, 3h, 130grad, partielle Umlagerung;
Chalcon (R2=4-Cl), Ethylenglykol;

YieldReaction ConditionsOperation in experiment
With methanol; platinum Hydrogenation;
With ethyl acetate; platinum Hydrogenation;
  • 14
  • [ 776297-03-1 ]
  • [ 5739-37-7 ]
  • 15
  • 3-acetoxy-1-(4-chloro-phenyl)-3-phenyl-propene [ No CAS ]
  • alcoholic KOH-solution [ No CAS ]
  • [ 5739-37-7 ]
  • [ 5739-39-9 ]
  • 16
  • [ 22966-22-9 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen In methanol for 20h;
98% With hydrogen In methanol at 20℃; for 20h;
98% With hydrogen In methanol at 20℃; for 24h;
97% With diphenyl sulfide; hydrogen In methanol at 20℃; for 24h;
97% With diphenyl sulfide; hydrogen In methanol at 20℃; for 24h;
96% With ammonium acetate; zinc In ethanol at 20℃; for 1.25h;
92% With 9-borabicyclo[3.3.1]nonane dimer; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In ethyl acetate at 40℃; for 16h;
90% With sodium tetrahydroborate; nickel dichloride In methanol; water at 20℃; for 0.5h;
90% With ammonium chloride; zinc In ethanol; water at 20℃; for 0.75h;
86% With magnesium; zinc(II) chloride for 0.416667h;
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; cerium(III) chloride monohydrate / methanol / 0.17 h 2: sodium t-butanolate; 1,10-Phenanthroline / toluene / 2 h / 80 °C / Inert atmosphere

Reference: [1]Sajiki, Hironao; Ikawa, Takashi; Yamada, Hiromi; Tsubouchi, Kozo; Hirota, Kosaku [Tetrahedron Letters, 2003, vol. 44, # 1, p. 171 - 174]
[2]Ikawa, Takashi; Sajiki, Hironao; Hirota, Kosaku [Tetrahedron, 2005, vol. 61, # 8, p. 2217 - 2231]
[3]Kitamura, Yoshiaki; Tanaka, Asami; Sato, Mutsumi; Oono, Keiji; Ikawa, Takashi; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao [Synthetic Communications, 2007, vol. 37, # 24, p. 4381 - 4388]
[4]Mori, Akinori; Miyakawa, Yumi; Ohashi, Eri; Haga, Tomoko; Maegawa, Tomohiro; Sajiki, Hironao [Organic Letters, 2006, vol. 8, # 15, p. 3279 - 3281]
[5]Mori, Akinori; Mizusaki, Tomoteru; Miyakawa, Yumi; Ohashi, Eri; Haga, Tomoko; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao [Tetrahedron, 2006, vol. 62, # 51, p. 11925 - 11932]
[6]Zhou, Yong-Bo; Wang, Yu-Iu; Wang, Jin-Ye [Journal of Chemical Research, 2004, # 2, p. 118 - 119]
[7]Nicholson, Kieran; Langer, Thomas; Thomas, Stephen P. [Organic Letters, 2021, vol. 23, # 7, p. 2498 - 2504]
[8]Khurana, Jitender Mohan; Sharma, Purnima [Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 3, p. 549 - 552]
[9]Li, Jian-Ping; Zhang, Yong-Xia; Ji, Yan [Journal of the Chinese Chemical Society, 2008, vol. 55, # 2, p. 390 - 393]
[10]Saikia, Anil; Barthakur, Madan Gopal; Boruah, Romesh Chandra [Synlett, 2005, # 3, p. 523 - 525]
[11]Zheng, Hong-Xing; Xiao, Zu-Feng; Yao, Chuan-Zhi; Li, Qiang-Qiang; Ning, Xiao-Shan; Kang, Yan-Biao; Tang, Yong [Organic Letters, 2015, vol. 17, # 24, p. 6102 - 6105]
  • 17
  • [ 69519-09-1 ]
  • [ 346608-05-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
90% With dodecacarbonyl-triangulo-triruthenium In toluene at 140℃; for 20h;
  • 18
  • [ 292638-84-7 ]
  • [ 790-41-0 ]
  • [ 5739-37-7 ]
  • [ 126866-24-8 ]
  • 19
  • [ 98-54-4 ]
  • [ 22966-22-9 ]
  • 6-tert-butyl-2-(4-chlorophenyl)-4-phenyl-2H-chromen-2-ol [ No CAS ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
1: 69% 2: 68% With trifluoroacetic acid for 72h; Heating;
  • 20
  • [ 99-91-2 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / sodium borohydride; nickel(II) chloride hexahydrate / methanol; H2O / 0.5 h / 20 °C
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 20 °C / Inert atmosphere 2.1: magnesium(II) perchlorate; 1,3-Dimethyl-2,3-dihydro-1H-benzoimidazole / toluene / 24 h / 80 °C / Inert atmosphere 2.2: 0.17 h / Irradiation
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 20 °C 2: sodium tetrahydroborate; cerium(III) chloride monohydrate / methanol / 0.17 h 3: sodium t-butanolate; 1,10-Phenanthroline / toluene / 2 h / 80 °C / Inert atmosphere
  • 21
  • [ 100-52-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / sodium borohydride; nickel(II) chloride hexahydrate / methanol; H2O / 0.5 h / 20 °C
  • 22
  • [ 104-88-1 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Mg 2: 74 percent / dichromate
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 2: palladium diacetate; triethylamine / acetonitrile / 24 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: palladium diacetate; triethylamine / acetonitrile / 80 °C / Inert atmosphere
  • 23
  • [ 103-63-9 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Mg 2: 74 percent / dichromate
  • 24
  • [ 5739-37-7 ]
  • [ 113478-84-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / bromine / acetic acid / 50 °C 2: 33 percent / sodium acetate / methanol / 6 h / Heating
  • 25
  • [ 100-39-0 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: alcohol 2: barium hydroxide
  • 26
  • [ 122-01-0 ]
  • phenethylzinc iodide [ No CAS ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
94% With [palladium(II)dichloride(1,10-phenanthroline)] In acetonitrile at 20℃; for 2h; Inert atmosphere;
  • 27
  • [ 3391-10-4 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
  • [ 6948-70-5 ]
YieldReaction ConditionsOperation in experiment
80% With benzaldehyde; potassium hydroxide at 110℃; for 32h; Schlenk technique; Inert atmosphere; Green chemistry;
With potassium hydroxide In toluene for 4h; Reflux;
93 %Spectr. With trans-RuCl(2-(2-pyridyl-6-ol)-1,10-phenanthroline)(PPh3)2PF6; sodium hydroxide In toluene at 125℃; for 1.5h; Schlenk technique; Glovebox; Inert atmosphere;
With [(6,6’-dihydroxy-2,2’-bipyridine)Ru(H)(CO)(PPh3)2]Cl; potassium <i>tert</i>-butylate In toluene at 130℃; for 1.25h; Inert atmosphere; Schlenk technique;
With C53H44N3O2P2Ru(1+)*Cl(1-); potassium <i>tert</i>-butylate In toluene at 110℃; for 1h; Schlenk technique; Inert atmosphere;
With C51H41N3O2P2RuS; potassium <i>tert</i>-butylate In toluene at 110℃; for 1h; Schlenk technique; Inert atmosphere;
With [{MeO-C5H3N-C5H3N-CH(O)-C6H4-PPh2}Ru(CO)(PPh3)]Cl; potassium <i>tert</i>-butylate In toluene for 1.5h; Inert atmosphere; Schlenk technique; Reflux;
With potassium <i>tert</i>-butylate; C34H42Br2N6Ru2 In toluene; acetonitrile at 120℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;

  • 28
  • [ 956-02-5 ]
  • [ 5739-37-7 ]
  • C15H13ClO [ No CAS ]
  • C15H15ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Rhizopus arrhizus NCIM 878 In ethanol; water at 30℃; Microbiological reaction;
  • 29
  • [ 956-02-5 ]
  • [ 5739-37-7 ]
  • [ 6948-70-5 ]
YieldReaction ConditionsOperation in experiment
With sodium formate In water at 100℃; for 12h; chemoselective reaction;
With palladium; sodium formate In water at 100℃; for 8h; chemoselective reaction;
  • 30
  • [ 100-52-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 20 °C / Inert atmosphere 2.1: anhydrous magnesium perchlorate; 1,3-Dimethyl-2,3-dihydro-1H-benzoimidazole / toluene / 24 h / 80 °C / Inert atmosphere 2.2: 0.17 h / Irradiation
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; lithium hydroxide monohydrate / 20 °C 2: sodium tetrahydridoborate; cerium(III) chloride monohydrate / methanol / 0.17 h 3: sodium tertiary butoxide; 1,10-Phenanthroline / toluene / 2 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: C42H36ClIrO2P2; formalin; triethylamine / 1,2-dimethoxyethane / 20 h / 80 °C / Schlenk technique; Inert atmosphere 2: potassium hydroxide; Sodium sulfate [anhydrous]; C44H35ClO4P2Ru / toluene / 16 h / 150 °C / Inert atmosphere; Schlenk technique
Multi-step reaction with 2 steps 1: isopropanol; [Ru(P(Ph){(o-C6H4)(1,2,3-N3C(Ph)CH)}2)(Cl)(PPh3)(H2O)]Cl; potassium hydroxide / 3 h / 80 °C / Inert atmosphere 2: [Ru(P(Ph){(o-C6H4)(1,2,3-N3C(Ph)CH)}2)(Cl)(PPh3)(H2O)]Cl; potassium hydroxide / 1,4-dioxane / 12 h / 120 °C / Inert atmosphere

  • 31
  • [ 3277-89-2 ]
  • [ 122334-37-6 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
90% In tetrahydrofuran at 20℃; for 2h; Cooling with ice; 2 Representative standard procedures for the synthesis of ketones 12 General procedure: To an ice-cold solution of theWeinreb amide (2.0 mmol) in 8mL of anhydrous THF was added dropwise a solution of alkyl magnesium bromide (2.1 mmol) in THF. The mixture stirred at the same temperature for 2 h. The reaction was quenched by addition of an aqueous 10% HCl solution (15 mL) and stirred for 5 min. The resulting solution was extracted with EtOAc and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under vacuum after filtration. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) to offer the pure product 12. 4.1.2.2 1-(4-Chlorophenyl)-3-phenylpropan-1-one 12e According to the representative procedure above, the title compound was obtained as a white solid (1.1 g, 90%) from the corresponding amide (5 mmol). Rf = 0.65 (petroleum ether/EtOAc 3:1); m.p. = 69 °C; IR (KBr): = 3025, 2924, 1681, 1586, 1485, 1396, 1204, 1093 cm-1; 1H NMR (300 MHz, CDCl3): δ = 7.92-7.88 (m, 2H), 7.46-7.42 (m, 2H), 7.20-7.32 (m, 5H), 3.31-3.26 (m, 2H), 3.10-3.00 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3): δ = 198.0, 141.1, 139.5, 135.2, 129.5, 129.0, 128.6, 128.5, 126.3, 40.5, 30.1 ppm; MS (E.I., 70 eV) m/z 244, 209, 141, 139 (100), 113, 111, 105, 104, 103, 91, 77, 75.
  • 32
  • [ 5739-37-7 ]
  • [ 104146-76-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine; acetic acid / N,N-dimethyl-formamide / 1 h / 90 °C 2: polystyrene-supported TBD; Amberlyst® A-15 / acetonitrile / 24 h / 50 °C
  • 33
  • [ 5739-37-7 ]
  • [ 64412-56-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine; acetic acid / N,N-dimethyl-formamide / 1 h / 90 °C 2: polystyrene-supported TBD; Amberlyst® A-15 / acetonitrile / 24 h / 60 °C
  • 34
  • [ 50-00-0 ]
  • [ 5739-37-7 ]
  • [ 1416358-60-5 ]
YieldReaction ConditionsOperation in experiment
With piperidine; acetic acid In N,N-dimethyl-formamide at 90℃; for 1h; 2 Representative standard procedures for the synthesis of enones 8 General procedure: To a stirred solution of ketone (1 mmol) in DMF (2 mL) was successively added paraformaldehyde (150 mg), piperidine (0.052 mL) and AcOH (0.052mL). The resulting mixture was heating at 90 C for 1 h. After cooling,waterwas added to the residue and the mixture was extracted with Et2O. The combined organic layers was washed with water, dried over MgSO4, filtered, and concentrated in vacuo to give quantitatively the corresponding enone 9. The rather unstable crude productwasusedrapidly without furtherpurification. 4.1.3.2 2-Benzyl-1-(4-chlorophenyl)prop-2-en-1-one 8e According to the representative procedure above, the title compound was obtained as a pale yellow oil (255 mg, 100% crude) from the corresponding ketone. Rf = 0.42 (petroleum ether/Et2O 4:1); 1H NMR (300 MHz, CDCl3): δ = 7.59-7.54 (m, 2H), 7.29-7.07 (m, 7H), 5.66 (s, 1H), 5.54 (s, 1H), 3.69 (s, 2H) ppm; 13C NMR (75 MHz, CDCl3): δ = 196.4, 147.5, 138.7, 138.5, 136.0, 130.9, 129.2, 128.7, 128.6, 126.5, 38.4; MS (E.I., 70 eV) m/z = 255, 241, 221 (100), 203, 178, 165, 139, 111.
  • 35
  • [ 91-01-0 ]
  • [ 5739-37-7 ]
  • [ 6948-70-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / 16 h / 135 °C / Inert atmosphere; Schlenk technique 2: benzaldehyde; potassium hydroxide / 32 h / 110 °C / Schlenk technique; Inert atmosphere; Green chemistry
  • 36
  • [ 3946-29-0 ]
  • [ 98-80-6 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; Wilkinson's catalyst; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 20h; Inert atmosphere;
  • 37
  • [ 3946-29-0 ]
  • [ 22422-21-5 ]
  • [ 98-80-6 ]
  • [ 5739-37-7 ]
  • [ 5012-90-8 ]
  • 38
  • [ 99-91-2 ]
  • [ 100-52-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydroxide In water for 24h;
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 4 h / 0 - 20 °C 2: acetoxy(2,6-bis((diphenylphosphino)methyl)-3,5-dimethylphenyl)palladium(II); butan-1-ol; potassium carbonate / 1 h / Reflux
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethanol / 0 - 20 °C 2: ammonium chloride; methanol / dimethyl sulfoxide / 6 h / 20 °C / Electrochemical reaction
  • 39
  • [ 591-50-4 ]
  • [ 147849-98-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
90% With palladium 10% on activated carbon; sodium carbonate In ethanol; water at 100℃; for 6h; Representative Experimental Procedure General procedure: To a mixtureof 2-(hydroxy(phenyl)methyl)acrylate (1a) (100 mg, 0.48mmol, 1.2 eq), iodobenzene (2a) (82.5 mg, 0.045 mL, 0.40mmol), and a sodium carbonate (103 mg, 0.97 mmol, 2.4eq.) in a solution of water and ethanol (3 mL, 1:1) in 5 mL vial was added 10% Pd/C (8.5 mg, 2.0 mol %). After the resulting mixture was heated 100°C at 6 h, the reaction mixture was cooled, extracted with an solution (2 mL × 5) ofethyl acetate and hexane (1:2). The extracts was concentrated and chromatographed on silica gel column using a solution of ethyl acetate and hexane (1:4) to give a decarboxylative coupling product 3a, 1,3-Diphenylpropan-1-one, in 86% isolated yield (Table 1. entry 1).
  • 40
  • [ 3391-10-4 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
99% With Cu-Ag supported on hydrotalcite In o-dimethylbenzene at 150℃; for 12h; Inert atmosphere;
95% With C42H36ClIrO2P2; potassium hydroxide In para-xylene at 130℃; for 12h; Inert atmosphere; Schlenk technique; Molecular sieve;
95% With C44H35ClO4P2Ru; Sodium sulfate [anhydrous]; potassium hydroxide In toluene at 150℃; for 16h; Inert atmosphere; Schlenk technique; chemoselective reaction;
92% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; 2-(2-(diphenylphosphanyl)phenyl)benzo[d]oxazole; potassium hydroxide In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere; 4.3. General procedure for alkylation reactions General procedure: [Cp*IrCl2]2 (1 mol %, 0.01 mmol, 8.0 mg), 4a (2 mol %, 0.02 mmol,7.6 mg), KOH (10 mol %, 0.1 mmol, 5.6 mg), and toluene (5 mL) wereadded to a 25mL Schlenk tube with stirring under N2 at roomtemperature. Then ketones/secondary alcohols/amines (1 mmol),primary alcohols (1.1 mmol) were added by syringe. The reactionmixture was heated to 110 °C under reflux in an oil bath for 24 h. Itwas cooled to ambient temperature. Then it was concentrated invacuo, and purified by flash column chromatography with petroleumether/ethyl acetate to afford the corresponding alkylatedproduct.
91% With potassium-t-butoxide; C20H20Cl3N7Ru*H2O In toluene at 120℃; for 12h; Sealed tube;
87% With [Ni(dmpymt)2]6; potassium hydroxide In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;
87% With C33H40ClN4Ru(1+)*F6P(1-); potassium hydroxide In toluene at 120℃;
78% With [Co(N,N'-bis(α-pyridyl)-2,6-diaminopyridine)Cl2]; sodium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Molecular sieve; Schlenk technique; 4.9. Typical procedure for syntheses of α-alkylated ketones General procedure: Under an N2 atmosphere, a mixture of secondary alcohol (0.5 mmol), primary alcohol (0.6 mmol), 1a (5 mol %), NaOH (0.1 mmol), 4 Å molecular sieve (0.6 g), and toluene (1.5 mL) was added into a 25 mL Schlenk tube equipped with a stirring bar. The mixture was heated to 120 °C under a slow and steady N2 flow for 24 h. After cooling to ambient temperature, 6 mL water was added and the aqueous solution extracted with ethyl acetate (3 x 5 mL). The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product purified on a short flash chromatography column.
78% With potassium hydroxide In toluene at 110℃; for 18h; chemoselective reaction;
76% In para-xylene at 120℃; for 8h; Inert atmosphere; Green chemistry;
72% With C27H24Cl3F6IrN2; potassium hydroxide In toluene at 130℃;
69% With C16H13MnN5O3(1+)*Br(1-); sodium hydroxide In tert-Amyl alcohol at 110℃; for 6h; Green chemistry;
68% With C27H42ClN2PRu; Cs2CO3 In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 48h; Inert atmosphere; Glovebox; Sealed tube;

Reference: [1]Xu, Jin; Yue, Hongmei; Liu, Sheng; Wang, Hanfei; Du, Yuqun; Xu, Chunli; Dong, Wensheng; Liu, Chunling [RSC Advances, 2016, vol. 6, # 29, p. 24164 - 24174]
[2]Musa, Sanaa; Ackermann, Lutz; Gelman, Dmitri [Advanced Synthesis and Catalysis, 2013, vol. 355, # 14-15, p. 3077 - 3080]
[3]Mujahed, Shrouq; Valentini, Federica; Cohen, Shirel; Vaccaro, Luigi; Gelman, Dmitri [ChemSusChem, 2019, vol. 12, # 20, p. 4693 - 4699]
[4]Huang, Shuang; Wu, Si-Peng; Zhou, Quan; Cui, He-Zhen; Hong, Xi; Lin, Yue-Jian; Hou, Xiu-Feng [Journal of Organometallic Chemistry, 2018, vol. 868, p. 14 - 23]
[5]Bhattacharyya, Dipanjan; Sarmah, Bikash Kumar; Nandi, Sekhar; Srivastava, Hemant Kumar; Das, Animesh [Organic Letters, 2021, vol. 23, # 3, p. 869 - 875]
[6]Zhang, Meng-Juan; Li, Hong-Xi; Young, David J.; Li, Hai-Yan; Lang, Jian-Ping [Organic and Biomolecular Chemistry, 2019, vol. 17, # 14, p. 3567 - 3574]
[7]Maji, Ankur; Singh, Anshu; Singh, Neetu; Ghosh, Kaushik [ChemCatChem, 2020, vol. 12, # 11, p. 3108 - 3125]
[8]Zhang, Shi-Qi; Guo, Bin; Xu, Ze; Li, Hong-Xi; Li, Hai-Yan; Lang, Jian-Ping [Tetrahedron, 2019, vol. 75, # 47]
[9]Hu, Qiyan; Huang, Fei; Qin, Feng; Tang, Lin; Xu, Dongping; Zhang, Wu [Applied Organometallic Chemistry, 2022]
[10]Liu, Xiang; Ding, Ran-Sheng; He, Lin; Liu, Yong-Mei; Cao, Yong; He, He-Yong; Fan, Kang-Nian [ChemSusChem, 2013, vol. 6, # 4, p. 604 - 608]
[11]Genç, Sertaç; Günnaz, Salih; Çetinkaya, Bekir; Gülcemal, Süleyman; Gülcemal, Derya [Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2875 - 2881]
[12]Lan, Xiao-Bing; Ye, Zongren; Liu, Jiahao; Huang, Ming; Shao, Youxiang; Cai, Xiang; Liu, Yan; Ke, Zhuofeng [ChemSusChem, 2020, vol. 13, # 10, p. 2557 - 2563]
[13]Chang, Weihong; Gong, Xue; Wang, Shuizhong; Xiao, Ling-Ping; Song, Guoyong [Organic and Biomolecular Chemistry, 2017, vol. 15, # 16, p. 3466 - 3471]
  • 41
  • [ 98-00-0 ]
  • [ 3391-10-4 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
87% With C38H43ClIrN2O2P; caesium carbonate; silver(I) triflimide In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere;
  • 42
  • [ 100-42-5 ]
  • [ 69556-14-5 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: cobalt(II) bromide; 1,1'-bis(diisopropylphosphino)ferrocene; zinc / acetonitrile / 60 °C 2: Acidic conditions
  • 43
  • C21H19ClN2 [ No CAS ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Acidic conditions;
  • 44
  • [ 5739-37-7 ]
  • C15H14ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium acetate In methanol
With hydroxylamine hydrochloride; sodium acetate In ethanol
  • 45
  • [ 5739-37-7 ]
  • 3-(4-chlorophenyl)-5-phenyl-4,5-dihydroisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / methanol 2: Selectfluor; tetra-(n-butyl)ammonium iodide / 1,2-dichloro-ethane; water / 3 h / 45 °C
  • 46
  • [ 3391-10-4 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) / tert-Amyl alcohol / 6 h / Reflux 2: Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); caesium carbonate / tert-Amyl alcohol / 6 h / Reflux
  • 47
  • [ 58824-54-7 ]
  • [ 873-55-2 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
40% With 4,7-Dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; copper (II) trifluoroacetate hydrate In 1,4-dioxane at 100℃; for 20h; Sealed tube; regioselective reaction;
  • 48
  • [ 166823-88-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
86% With 1,10-Phenanthroline; sodium t-butanolate In toluene at 80℃; for 2h; Inert atmosphere;
  • 49
  • [ 99-91-2 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
  • [ 3391-10-4 ]
  • [ 6948-70-5 ]
YieldReaction ConditionsOperation in experiment
1: 71% 2: 16 %Spectr. 3: 6 %Spectr. With tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; caesium carbonate; triphenylphosphine In toluene at 140℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;
  • 50
  • [ 873-73-4 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 4-n-chlorophenylacetylene With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water; silver trifluoromethanesulfonate In 1,4-dioxane at 120℃; for 1h; Microwave irradiation; Stage #2: benzyl alcohol With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium <i>tert</i>-butylate In 1,4-dioxane at 130℃; for 2h; Microwave irradiation; 24 1-(4-chlorophenyl)-3-phenylpropan-1-one The [(IPr) AuCl] (6mg, 0.01mmol, 1mol%), AgOTf (2.6mg, 0.01mmol, 1mol%), 4- chlorophenyl acetylene (136mg, 1mmol), 1,4- dioxane (1ml ) and water (36ul, 2equiv.) were successively added to 5ml microwave tube.After the reaction mixture was microwaved at 120 reactor for one hour, cooled to room temperature.Thereto was added [Cp * IrCl2]2(8mg, 0.01mmol, 1mol%), potassium tert-butoxide (34mg, 0.3mmol, 0.3equiv.), Benzyl alcohol (130mg, 1.2mmol).After the reaction mixture was microwaved at 130 reactor and then reacted for 2 hours, cooled to room temperature.Filtered, and solvent was removed by rotary evaporation, then purified by column chromatography (developing solvent: petroleum ether / ethyl acetate) to give the pure title compound Yield: 86%
  • 51
  • [ 591-50-4 ]
  • [ 58824-54-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
79% With palladium diacetate; triethylamine In acetonitrile at 80℃; for 24h; Inert atmosphere;
With palladium diacetate; triethylamine In acetonitrile at 80℃; Inert atmosphere;
With palladium diacetate; triethylamine In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 52
  • [ 5739-37-7 ]
  • 1-(4-chlorophenyl)-1-methylindane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 12 h / 65 °C / Inert atmosphere; Schlenk technique 2.1: trifluoroacetic acid / 24 h / 80 °C / Schlenk technique; Inert atmosphere
  • 53
  • [ 867-13-0 ]
  • [ 5739-37-7 ]
  • ethyl (2E)-3-(4-chlorophenyl)-5-phenylpent-2-enoate [ No CAS ]
  • ethyl 3-(4-chlorophenyl)-5-phenylpent-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydride In tetrahydrofuran at 0 - 60℃; Inert atmosphere; GP-1 (General Procedure for Witting-Horner-Wadsworth-Emmons reaction of 1,3-diphenylpropan-1-ones) General procedure: To an oven dried round bottom flask under nitrogen atmosphere charged with 60% NaH (120 mg, 3.0mmol), THF (10 mL) and cooled to ice temperature. Then TEPA (0.9 ml, 4.5 mmol) was added drop-wiseuntil the solution becomes a clear solution. To the resulted yield, 1,3-diphenylpropan-1-ones 6 (315-399 mg,1.5 mmol) was added, the reaction mixture was stirred at 0 °C for 30 minutes and then heated at 60 °C for 6 to12 h. Progress of the reaction was monitored by TLC until the reaction was completed. The reaction mixturewas quenched by the addition of aqueous NH4Cl and extracted with ethyl acetate (3 × 20 mL). The combinedorganic layers were washed with saturated NaCl solution, dried (Na2SO4) and concentrated under reducedpressure. Purification of the residue by silica gel column chromatography (petroleum ether/ethyl acetate)furnished the pendant β-aryl α,β-unsaturated ester 3 (84-96 %).
1: 42% 2: 45% Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: 4'-chloro-3-phenylpropiophenone In tetrahydrofuran; mineral oil at 65℃; for 12h; Inert atmosphere; Schlenk technique;
  • 54
  • [ 89-95-2 ]
  • [ 3391-10-4 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 1-(p-chlorophenyl)ethyl alcohol With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In tert-Amyl alcohol at 20℃; for 6h; Reflux; Stage #2: 2-methyl-benzyl alcohol With caesium carbonate In tert-Amyl alcohol for 6h; Reflux; 22 Example 22: 1- (4-Chlorophenyl) -3-phenyl-1-propanone A mixture of 1- (4-chlorophenyl) ethanol (5.3 mg, 0.01 mmol, 1 mol%) and tert-amyl alcohol (1 mL) were successively added to a 5 mL round bottom flask. The reaction mixture was refluxed in air for 6 hours and then cooled to room temperature. Then, cesium carbonate (33 mg, 0.1 mmol, 0.1 equiv.) And benzyl alcohol (119 mg, 1.1 mmol) were added, refluxed in air for 6 hours, and then cooled to room temperature. The solvent was removed by rotary evaporation and then the title compound was purified by column chromatography (developing solvent: petroleum ether / ethyl acetate) in 82%
  • 55
  • [ 103-64-0 ]
  • [ 873-76-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
94.4% With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,4-di(diphenylphosphino)-butane; bis-[(trifluoroacetoxy)iodo]benzene In N,N-dimethyl-formamide at 100℃; for 8h; 2 Example 2 To a solution of N, N-dimethylformamide (DMF) in a volume ratio of 4: 1 with polyethylene glycol 200(PEG-200)) was added 100 mmol of the compound of the above formula (I), 80 mmol of the compound of the above formula (II), 7 mmol of catalyst bis (triphenylphosphine) cyclopentadienyl ruthenium chloride, 150 mmol of an oxidizing agent bis Fluoroacetic acid) iodobenzene (PhI (TFA) 2), 10 mmol of organic ligand L1 and 100 mmol of base, 5,7-triazabicyclo [4.4.0] dec-5-ene (TBD)To 100 & lt; 0 & gt; C and the reaction was stirred at this temperature for 8 hours;After completion of the reaction, the reaction system is naturally cooled to room temperature and the pH is adjusted to neutral, filtered and the filtrate is saturatedWashed with brine and extracted with ethyl acetate 2-3 times. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography at a 1: 2 by volume mixture of chloroform and petroleum ether Followed by elution to give the compound of formula (III) in a yield of 94.4%.
  • 56
  • [ 100-42-5 ]
  • [ 74-11-3 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
62% With potassium phosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane; dimethyl dicarbonate In acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Sealed tube;
62% With 2,4,6-trimethyl-pyridine; methylene blue; triphenylphosphine In N,N-dimethyl acetamide at 20℃; Inert atmosphere; Irradiation; 4 Weigh (31mg, 0.2mmol), photocatalyst Methylene blue (5.6mg, 2%), 2,4,6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to the reaction flask, replaced with nitrogen three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N,N-dimethylacetamide solvent, under nitrogen atmosphere, slowly add to the reaction flask, place the reaction flask under white LEDs, and react at room temperature for 24-36h. After the reaction is over, add 15 mL of water, extract with ethyl acetate (3x10 mL), stand still, separate into layers, pour out the lower aqueous phase, combine the organic phases, dry the organic phase with anhydrous sodium sulfate, and evaporate the organic phase, dry loading, column chromatography (petroleum ether: ethyl acetate) to obtain 30 mg of the target product with a yield of 62%.
  • 57
  • [ 14371-10-9 ]
  • [ 1679-18-1 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
89% With rhodium(II) acetate dimer; water; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 90℃; for 4h; Inert atmosphere; Sealed tube;
  • 58
  • [ 5739-37-7 ]
  • Grushin’s reagent [ No CAS ]
  • [ 1226965-57-6 ]
YieldReaction ConditionsOperation in experiment
39% With ammonium peroxydisulfate; tert-butyldimethylsilane; trifluoroacetic acid In water; acetone at 20℃; for 18h; Inert atmosphere; Sealed tube; Irradiation; Green chemistry;
  • 59
  • [ 536-74-3 ]
  • [ 873-76-7 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
50% With potassium <i>tert</i>-butylate In toluene at 125℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; Green chemistry; regioselective reaction;
  • 60
  • [ 99-91-2 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
  • [ 6948-70-5 ]
YieldReaction ConditionsOperation in experiment
1: 87% 2: 13% With C30H30ClIrN4; potassium hydroxide In toluene at 130℃; for 2h;
1: 75% 2: 25% With C26H42ClN2Ru(1+)*F6P(1-); potassium hydroxide In toluene at 120℃; for 2h;
  • 61
  • [ 99-91-2 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
  • [ 956-02-5 ]
YieldReaction ConditionsOperation in experiment
1: 81.9% 2: 18.1% With potassium hydroxide In toluene at 100℃; for 10h; Sealed tube; Irradiation;
  • 62
  • [ 100-42-5 ]
  • [ 104-88-1 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
54% With Eosin Y In fluorobenzene at 80℃; Irradiation; regioselective reaction; Ethyl 4-(3-Phenylpropanoyl)benzoate (8) General procedure: A 10 mL reaction tube equipped with a magnetic stirrer bar wascharged with ethyl 4-formylbenzoate (1.0 mmol, 5.0 equiv),styrene (0.2 mmol, 1.0 equiv), eosin Y (0.01 mmol, 0.05 equiv),and PhF (4 mL). The tube was then sealed and degassed by usingan argon balloon with a subsequent backfill with argon. Thetube was then equipped with an argon balloon and placedunder blue LEDs (3 m strip; 27 W) and irradiated for 72 h at80 °C. The solvent was removed on a rotary evaporator underreduced pressure, and the residue was purified by column chromatography[silica gel, hexane-EtOAc (15:1 to 1:1)] to give acolorless liquid
  • 63
  • [ 100-51-6 ]
  • [ 1777-56-6 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
75.2% With potassium <i>tert</i>-butylate; C16H35BrMnN3O2P2 In 1,4-dioxane at 120℃; for 16h; Inert atmosphere;
  • 64
  • [ 536-38-9 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene / 24 h / 23 °C 2: sodium hydroxide / water; dichloromethane / 3 h 3: potassium <i>tert</i>-butylate; C16H35BrMnN3O2P2 / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
  • 65
  • [ 2689-81-8 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / water; dichloromethane / 3 h 2: potassium <i>tert</i>-butylate; C16H35BrMnN3O2P2 / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
  • 66
  • [ 5739-37-7 ]
  • [ 22966-22-9 ]
YieldReaction ConditionsOperation in experiment
98% With iron(III) chloride; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Schlenk technique;
  • 67
  • [ 16616-42-5 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
84% With methanol; diphenyl sulfide; N,N,N,N-tetraethylammonium tetrafluoroborate In acetonitrile at 20℃; for 6h; Electrochemical reaction; Inert atmosphere;
  • 68
  • [ 2788-86-5 ]
  • [ 100-51-6 ]
  • [ 5739-37-7 ]
YieldReaction ConditionsOperation in experiment
82% With [IrCl(cis,cis-1,5-cyclooctadiene)(1,3-bis(2,4,6-trimethyl-phenyl)imidazol-2-ylidene)]; caesium carbonate In tert-Amyl alcohol at 140℃; for 16h;
  • 69
  • [ 5739-37-7 ]
  • 3-(4-chlorophenyl)-5-phenyl-4,5-dihydroisoxazole [ No CAS ]
  • [ 24097-17-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Oxone; potassium iodide / acetonitrile / 48 h / 50 °C
  • 70
  • [ 5739-37-7 ]
  • 3-(4-chlorophenyl)-5-phenyl-4,5-dihydroisoxazol-5-ol [ No CAS ]
  • 3-(4-chlorophenyl)-5-phenyl-4,5-dihydroisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol 2: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 24 h / 20 °C / Inert atmosphere
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