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[ CAS No. 7473-98-5 ] {[proInfo.proName]}

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Chemical Structure| 7473-98-5
Chemical Structure| 7473-98-5
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Product Details of [ 7473-98-5 ]

CAS No. :7473-98-5 MDL No. :MFCD00040710
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :C6H5COC(CH3)2OH InChI Key :XMLYCEVDHLAQEL-UHFFFAOYSA-N
M.W : 164.20 Pubchem ID :81984
Synonyms :

Calculated chemistry of [ 7473-98-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.45
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 1.91
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.07
Solubility : 1.41 mg/ml ; 0.00859 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 1.92 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.427 mg/ml ; 0.0026 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 7473-98-5 ]

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 [ 7473-98-5 ]

* 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 [ 7473-98-5 ]

[ 7473-98-5 ] Synthesis Path-Downstream   1~97

  • 1
  • [ 10409-54-8 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; diethyl ether
With sodium hydroxide
Multi-step reaction with 2 steps 1: 37 percent / diethyl ether; ethanol / 1 h / Ambient temperature 2: TsOH / H2O / Heating
Multi-step reaction with 2 steps 2: Me2CuLi
Multi-step reaction with 2 steps 2: aq. HCl
Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 2 h / 20 °C / Inert atmosphere 2: copper(l) iodide; <i>tert</i>-butyl alcohol / toluene / 16 h / 130 °C / Inert atmosphere

  • 2
  • [ 611-70-1 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
92.36% With di-tert-butyl peroxide In dichloromethane at 35℃; Sonication; 1; 2 Preparation of 2-hydroxy-2-methyl-1-phenyl-1-propanone 74.1 g (0.5 mol) of isobutyrylbenzene, dichloromethane (200 ml),219.34g (1.5mol) of di-tert-butyl peroxide was uniformly mixed, placed in an ultrasonic rod (45KHz), stirred vigorously, and the reaction temperature was controlled at about 35 °C.The reaction was carried out and the progress of the reaction was monitored using TLC or GC.After the completion of the reaction, an aqueous solution of sodium hydrogen sulfite (containing 187.3 g of sodium hydrogen sulfite) was slowly added dropwise to the reaction system.The quenching reaction was carried out and stirred until no peroxide was detected with the starch-potassium iodide test paper.Stirring was continued for another 30 min. Then the test paper was continued until there was no peroxide.Allow to stand, layer, and wash the organic layer with water until neutral.The methylene chloride is recovered by atmospheric pressure first, and then the solvent is further reduced under reduced pressure.After the solvent and the low-boiling substance were removed, the distillation was carried out under reduced pressure, and a fraction of 102-104 ° C / 4 mmHg was collected.The pale yellow liquid product was 75.82 g, the yield was 92.36%, and the GC content was 99.63%.
91.13% With oxygen; sodium hydroxide; sodium sulfite In ethanol at 15℃; for 6h; 16 Example 16 Synthesis of 2-hydroxy-2-methyl-1-phenylacetone To a 250 ml three-necked flask was added sodium hydroxide (8 g, 0.2 mol) and ethanol (150 ml) at 15 ° C,0.5h. Followed by the addition of sodium sulfite (25.21 g, 0.2 mol), 2-methyl-1-phenylacetone (29.64 g, 0.2 mol)1000ml size of the oxygen balloon, stirring reaction 6h.After completion of the reaction, the pH of the reaction solution was adjusted to 7 with 2M hydrochloric acid, and ethanol was distilled off under reduced pressure. Add 50 ml of water to(30 ml x 3), the combined organic phase was dried over anhydrous Na2SO4, and the mixture was partitioned with toluene. The solvent was evaporated to dryness to give 30.85 g of a light brown oil, 97% purity and 91.13% yield.
90% With oxygen; caesium carbonate; triethyl phosphite In dimethyl sulfoxide at 25℃; for 24h; Schlenk technique;
90.9% With tetrachloromethane; tetrabutylammomium bromide; sodium hydroxide at 60 - 70℃; for 6h; 3 One-pot chlorination and alkali hydrolysis section using carbon tetrachloride:In a 1000 ml three-necked flask, 140.7 g of crude isobutyrylbenzene, 4.22 g of tetrabutylammonium bromide, 219.6 g of carbon tetrachloride and 76.1 g of sodium hydroxide were added.Connect the condenser and heat and stir at 60-70 degrees for 6 hours.After completion of the reaction, the mixture was cooled to room temperature, diluted with 100 g of dichloromethane, and water was added. The organic layer was washed with saturated brine until neutral.Further, 141.7 g of the photoinitiator 173 was obtained by high vacuum distillation, and the yield was 90.9%.
88% With N-Bromosuccinimide; dimethyl sulfoxide at 100℃; for 24h;
86.5% Stage #1: phenyl isopropyl ketone With tetrabutylammomium bromide; sodium hydroxide In water at 82 - 85℃; Stage #2: With hexachloroethane In 1,1,2,2-tetrachloroethylene; water at 60 - 84℃; for 3h; 1 Example 1: Preparation of 2-hydroxy-2-methyl-1 -phenyl-1 -propanone A 500 mL double-walled-jacket, multi-necked flask, fitted with a mechanical stirrer,reflux condenser, connected to a thermostat, thermometer and a dropping funnel, ischarged with 59.3 g (400 mmol) isobutyrophenone, 2.58 g (8 mmol) tetrabutylammonium bromide and 373.3 g (2.80 mol) 30% aqueous sodium hydroxide solution. This is heated with stirring to 82-85 00, and within 90 minutes a solution of 94.7 g (408 mmol) hexachloroethane in 199 g tetrachloroethylene is added. Thereaction mixture is stirred for another 3 hours at 84 00 The temperature is then lowered to 60 00 and left unstirred for phase separation. The lower organic phase is split off; the aqueous phase is extracted with 50 g tetrachloroethylene, the organic phases are combined and 100 g water added. pH is then adjusted to 6.0 using 5% acetic acid. The organic phase is split off and distilled in vacuo.Yield: 56.8 g (86.5%) 2-Hydroxy-2-methyl-1 -phenyl-1 -propanone as a pale yellow oil; b.p. 96 00 1 mbar, 99% purity (GO). NMR data are identical with the data of an authentic reference sample.Tetrachloroethylene (b.p. 55 O 200 mbar) is nearly quantitatively recovered (94%,99.6% purity).
82.1% With dihydrogen peroxide In dichloromethane at 40℃; Microwave irradiation; 1 Preparation of 2-Hydroxy-2-methyl-1-phenyl-1-propanone 74.1 g (0.5 mol) of isobutyrylbenzene, 200 mL of dichloroethane, and 170.0 g (1.5 mol) of 30% hydrogen peroxide solution were uniformly mixed.Place the microwave reactor (power 300W) and stir it vigorously.And control the reaction temperature at about 40 °C,The reaction was monitored by TLC or GC. After the reaction was completed, microwave irradiation was performed. An aqueous sodium bisulfite solution (containing 187.3 g of sodium bisulfite) was slowly added to the reaction system, and the reaction was quenched for 2 hours. The mixture was allowed to stand still and the organic phase was separated. After washing with water, the solvent is recovered after decompression at atmospheric pressure, and the solvents and low-boiling impurities are removed.Distillation under vacuum distillation, collecting 102-103 ° C / 4mmHg fractions to give a light yellow oil 2-hydroxy-2-methyl-1-phenyl-1-propanone 66.7g, GC content was 99.5%, a yield of 82.1%.
80% With Pd2hpp4; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen In tetrahydrofuran at 6℃; for 12h; regioselective reaction;
70% With iodine; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; 21 Embodiment 212 - hydroxy -2 - methyl -1 - preparation of phenyl acetone Taking a 25 ml Schlenk reaction tube, iodize elemental (I2) 26 mg (0.1mmol) as catalyst, 2 - methyl -1 - phenyl acetone 75 mg (0.5mmol), dimethyl sulfoxide (DMSO) 1 ml as the oxidizing agent, carbonylating and solvent, for 100 °C stirring for 24 hours. After the reaction by adding ethyl acetate 15 ml, salt water 3 ml, ethyl acetate 3 times, the combined organic phase, column chromatography separation to obtain 2 - hydroxy -2 - methyl -1 - phenyl acetone pure product 57 mg, yield 70%.
65% Stage #1: phenyl isopropyl ketone With lithium diisopropyl amide In tetrahydrofuran; hexane for 0.5h; Cooling with acetone-dry ice; Stage #2: With MoO5*pyridine*HMPA In tetrahydrofuran; hexane at -22℃;
52% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 25℃; for 24h; Green chemistry;
44% With benzeneseleninic anhydride; sodium hydride In toluene Heating;
43% With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; dimethyl sulfoxide at 25℃; for 24h; Schlenk technique;
(i) LDA, THF, hexane, (ii) MoO5, Py, HMPT; Multistep reaction;
(i) Br2, dioxane, (ii) aq. NaOH, EtOH; Multistep reaction;
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: Et3N 2.1: O2 / [Cu(bpy)(BF4)2(H2O)2(bpy)]n / ethanol; H2O / 24 h / 0 °C / 760 Torr 2.2: 79 percent / triethyl phosphite / ethanol; H2O
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 2.5 h / -78 - 85 °C / Inert atmosphere; Green chemistry 2: 2,2,2-Trifluoroacetophenone; dihydrogen peroxide / acetonitrile; <i>tert</i>-butyl alcohol / 1 h / 20 °C / Green chemistry 3: toluene-4-sulfonic acid / 1 h / 20 °C / Green chemistry
96 mg With iodine; N,N-dimethyl-formamide; copper(II) oxide at 100℃; for 24h; Inert atmosphere;
With potassium <i>tert</i>-butylate; oxygen; triethyl phosphite In ethanol at 80℃; for 0.0833333h; Flow reactor;
Multi-step reaction with 2 steps 1: chlorine / 0.12 h / 160 °C / 3750.38 Torr / Flow reactor 2: sodium hydroxide / 0.18 h / 100 °C / Flow reactor

Reference: [1]Current Patent Assignee: JIAOCHENG ZHAOCHEN COAL COKE - CN109694310, 2019, A Location in patent: Paragraph 0028; 0031
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY; ZHEJIANG NHU CO., LTD. - CN106748693, 2017, A Location in patent: Paragraph 0039; 0040; 0041; 0042; 0043
[3]Liang, Yu-Feng; Jiao, Ning [Angewandte Chemie - International Edition, 2014, vol. 53, # 2, p. 548 - 552][Angew. Chem., 2014, vol. 53, # 2, p. 558 - 562,5]
[4]Current Patent Assignee: DAFENG XINYUANDA CHEMICAL - CN108892605, 2018, A Location in patent: Paragraph 0039; 0044; 0045; 0048
[5]Liang, Yu-Feng; Wu, Kai; Song, Song; Li, Xinyao; Huang, Xiaoqiang; Jiao, Ning [Organic Letters, 2015, vol. 17, # 4, p. 876 - 879]
[6]Current Patent Assignee: IGM COOP, B.V. - WO2018/197325, 2018, A1 Location in patent: Page/Page column 43
[7]Current Patent Assignee: TIANJIN JIURI NEW MATERIALS COMPANY LIMITED - CN107739303, 2018, A Location in patent: Paragraph 0015
[8]Chuang, Gary Jing; Wang, Weike; Lee, Eunsung; Ritter, Tobias [Journal of the American Chemical Society, 2011, vol. 133, # 6, p. 1760 - 1762]
[9]Current Patent Assignee: PEKING UNIVERSITY - CN104710256, 2017, B Location in patent: Paragraph 0153-0157
[10]Vedejs, Edwin; Larsen [Organic Syntheses, 1986, vol. 64, p. 127 - 127]
[11]Chaudhari, Moreshwar B.; Sutar, Yogesh; Malpathak, Shreyas; Hazra, Anirban; Gnanaprakasam, Boopathy [Organic Letters, 2017, vol. 19, # 13, p. 3628 - 3631]
[12]Yamakawa, Koji; Satoh, Tsuyoshi; Ohba, Nobuyuki; Sakaguchi, Reiji; Takita, Satoshi; Tamura, Nobuhiko [Tetrahedron, 1981, vol. 37, p. 473 - 480]
[13]Wang, Yongtao; Lu, Rui; Yao, Jia; Li, Haoran [Angewandte Chemie - International Edition, 2021, vol. 60, # 12, p. 6631 - 6638][Angew. Chem., 2021, vol. 133, # 12, p. 6705 - 6712,8]
[14]Vedejs,E. et al. [Journal of Organic Chemistry, 1978, vol. 43, p. 188 - 196]
[15]Ogata,Y. et al. [Journal of Organic Chemistry, 1977, vol. 42, p. 4061 - 4066]
[16]Arai, Takayoshi; Takasugi, Hitomi; Sato, Toru; Noguchi, Hiroshi; Kanoh, Hirofumi; Kaneko, Katsumi; Yanagisawa, Akira [Chemistry Letters, 2005, vol. 34, # 12, p. 1590 - 1591]
[17]Voutyritsa, Errika; Theodorou, Alexis; Kokotos, Christoforos G. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5708 - 5713]
[18]Liu, Weibing; Chen, Cui; Zhou, Peng [Journal of Organic Chemistry, 2017, vol. 82, # 4, p. 2219 - 2222]
[19]Kassin, Victor-Emmanuel H.; Gérardy, Romaric; Toupy, Thomas; Collin, DIégo; Salvadeo, Elena; Toussaint, François; Van Hecke, Kristof; Monbaliu, Jean-Christophe M. [Green Chemistry, 2019, vol. 21, # 11, p. 2952 - 2966]
[20]Current Patent Assignee: CHANGZHOU TRONLY NEW ELECTRONIC MATERIALS CO., LTD. - CN113493372, 2021, A
  • 3
  • [ 7721-20-2 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
79% With N-sulfonyloxaziridine (4a) In tetrahydrofuran; methanol for 0.25h; Ambient temperature;
  • 4
  • [ 676-85-7 ]
  • [ 7473-98-5 ]
  • Methanesulfinic acid 1,1-dimethyl-2-oxo-2-phenyl-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine at -78 - 0℃;
  • 5
  • [ 39158-85-5 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
99% With oxygen In ethanol at 20℃; for 72h;
79% Stage #1: 2-methyl-1-phenyl-1-trimethylsiloxy-1-propene With oxygen In ethanol; water at 0℃; for 24h; Stage #2: With triethyl phosphite In ethanol; water
69% With tris(dimethylamino)sulfonium trimethylsilyldifluoride; oxygen; triphenylphosphine In tetrahydrofuran at 0 - 5℃; for 2h;
With 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; tetrabutyl ammonium fluoride 1.) CHCl3, 60 deg C, 1 h, 2.) THF; Yield given. Multistep reaction;

  • 6
  • [ 55418-35-4 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
99% With trifluoroacetic acid In methanol for 2h;
  • 7
  • [ 7473-99-6 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydrogencarbonate for 72h; Ambient temperature;
94.8% With sodium hydroxide In water 1-6 54.9 g (0.3 mol) of 2-chloro-2-methyl-1-phenylpropan-1-one was added to the reaction flask. Add 55g of 25% sodium hydroxide aqueous solution to alkaline hydrolysis, Wash again, Distillation gave 46.7 g of pure photoinitiator 1173, Yield 94.8%, The content is 99.1%.
62% With diethyl methylmalonate anion In dimethyl sulfoxide Irradiation;
With sodium hydroxide; potassium chloride In water at 25℃;
With potassium hydroxide In ethanol
420 kg With tetrabutylammomium bromide; sodium hydroxide at 40℃; for 6h; Large scale; 1.3 (3) In a 3000 liter reactor,20% sodium hydroxide solution was added 2,000 kgAnd tetrabutylammonium bromide 2 kg,500 kg of the above chlorinated products,Keep the temperature no more than 40 degrees,After dripping for 6 hours,Gas chromatography detection of raw materials disappeared,Stop the reaction,Static stratification,The organic phase of the upper layer was subjected to vacuum distillation,Get the product 420 kg, content of 99.3%.
Alkaline conditions; 5 Alkaline reaction 2-methyl-1-phenyl-1-propyl ketone was added to the liquid base at a weight ratio of 1: 1.05,Stirring to the end of alkaline hydrolysis reaction;Then add petroleum ether extraction,Separate the water phase,De-dissolving,Recovery of petroleum ether,To give crude 2-hydroxy-2-methyl-1-phenyl-1-propyl ketone
With sodium hydroxide at 100℃; for 0.183333h; Flow reactor; 1-12 General procedure: (1) Friedel-Crafts reaction section 100: The acyl chloride, aluminum trichloride and the solvent required for Friedel-Crafts reaction are evenly mixed and placed in the first storage tank 1, benzene is placed in the second storage tank 2, and the first feeding pump P1 and The second feeding pump P2 adjusts the feed molar ratio of the flow control reactant, enters the micromixer 3 for mixing, and then enters the first microchannel reactor 4 to perform Friedel-Crafts reaction;(2) Friedel-Crafts reaction intermediate purification section 200: After the material stays in the first microchannel reactor 4 for a certain period of time, it enters the first gas-liquid separation tank 5 to separate hydrogen chloride gas, and absorbs hydrogen chloride tail gas with water to obtain hydrochloric acid; Friedel-Crafts reaction liquid (The first reaction liquid) After accumulating a certain amount in the first gas-liquid separation tank 5, it enters the quenching tank 7. The required hydrochloric acid is placed in the hydrochloric acid storage tank 6, and the metered hydrochloric acid is added by the third feeding pump P3, and under stirring For quenching, the heat generated by the circulating medium in the jacket is taken away, and the temperature of the quenching process is controlled. After the quenching is completed, let it stand for phase separation, take the organic phase GC to detect the conversion rate, and the water phase enters the waste acid tank 8 , The organic phase is in the Friedel-Crafts reaction liquid storage tank 9, and the fourth feeding pump P4 enters the first thin film evaporator 10 to separate the solvent and excess benzene, and the obtained Friedel-Crafts reaction intermediate enters the Friedel-Crafts reaction intermediate storage tank 11 , Excess benzene and recovered solvent enter the recovery solvent and benzene storage tank 12;(3) Chlorination reaction section 300: Friedel-Crafts reaction intermediates are fed into the micromixer 14 from the fifth feeding pump P5 to mix with the chlorine from the chlorine storage tank 13, adjust the chlorine inlet and outlet valves, control the chlorine flow and reaction pressure, and enter the first The chlorination reaction is carried out in the two microchannel reactor 15. The material stays in the second microchannel reactor 15 for a certain period of time and then enters the second gas-liquid separation tank 16 to separate the gas and the second reaction liquid, and sample the GC to detect the conversion rate. Alkaline solution absorbs exhaust gas;(4) Hydrolysis reaction section 400: The sodium hydroxide solution and phase transfer catalyst required for the hydrolysis reaction section are mixed and uniformly placed in the third storage tank 17, fed by the sixth feeding pump P6, and the chlorination reaction intermediate is fed by the seventh The pump P7 feeds materials, enters the micromixer 18 for mixing, and then enters the third microchannel reactor 19 for a certain period of time and then enters the buffer tank 20;(5) Product purification section 500: After a certain amount of material is accumulated in the buffer tank 20, it enters the phase separation tank 21 to stand for phase separation, and the excess sodium hydroxide is neutralized with the hydrochloric acid obtained in step (1), and the water phase enters the waste water tank 22 , The organic phase enters the crude product storage tank 23, the feed pump P8 is added to the second thin film evaporator 24 to distill and purify the finished product into the product storage tank 26, the reboiler enters the reboiler storage tank 25, and the purity of the finished product is detected by GC.

  • 8
  • [ 1443-80-7 ]
  • [ 609-08-5 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
37% With potassium <i>tert</i>-butylate In dimethyl sulfoxide Irradiation; RT., 4 h, 50 deg C, 19 h;
  • 9
  • [ 7473-98-5 ]
  • [ 20907-13-5 ]
YieldReaction ConditionsOperation in experiment
66% With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere;
With lithium aluminium tetrahydride
74 %Chromat. With [1,3-bis(3'-methylimidazole-2'-thione-κ-S)-5-methoxybenzene-κ-C]pentamethyl-η5-cyclopentadienyl rhodium(III) chloride; sodium hydroxide In isopropyl alcohol at 80℃; for 3h; Molecular sieve; 2.5. General procedure for the reduction of ketone compounds withhalf-sandwich rhodium complex General procedure: A mixture of ketones (0.1 mmol), NaOH (0.4 mmol, 4 equiv.),and half-sandwich rhodium complex (0.5 mol%) in 2-propanol(1.0 mL) was heated to 80 C in the presence of 4 Å molecular sievefor 3 h. After complete reaction (monitored by TLC), the reactionmixture was cooled to room temperature. The solvent wasremoved in vacuo, extracted with ethyl acetate and water(3 5 mL). The organic layers were analyzed by GC-MS chromatographyusing n-dodecane as an internal standa
84 %Chromat. With sodium methylate; C27H25Cl2NORu; isopropyl alcohol at 80℃; for 12h; Schlenk technique; Inert atmosphere;

  • 10
  • [ 7473-98-5 ]
  • [ 611-70-1 ]
YieldReaction ConditionsOperation in experiment
81% With potassium acetate; <i>L</i>-proline In dimethyl sulfoxide at 130℃; for 12h;
With hydrogenchloride (electrolysis);
Multi-step reaction with 2 steps 1: pyridine / 0.08 h / 0 - 100 °C 2: triethylamine; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; tris(bipyridine)ruthenium(II) dichloride hexahydrate / acetonitrile / 1 h / 20 °C / Inert atmosphere; UV-irradiation
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 2: diphenylsilane; zinc; nickel dichloride; magnesium chloride; 2-(2'-pyridyl)benzimidazole / N,N-dimethyl acetamide / 40 °C / Inert atmosphere; Schlenk technique

  • 11
  • [ 66086-33-7 ]
  • [ 7473-98-5 ]
  • 5,5-Dimethyl-4-phenyl-2,5-dihydro-furan-2,3-dicarboxylic acid di-tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triphenylphosphine In dichloromethane for 24h; Ambient temperature;
  • 12
  • [ 7473-98-5 ]
  • [ 762-42-5 ]
  • 5,5-Dimethyl-4-phenyl-2,5-dihydro-furan-2,3-dicarboxylic acid dimethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With triphenylphosphine In dichloromethane for 24h; Ambient temperature;
  • 13
  • [ 7473-98-5 ]
  • [ 762-21-0 ]
  • 5,5-Dimethyl-4-phenyl-2,5-dihydro-furan-2,3-dicarboxylic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With triphenylphosphine In dichloromethane for 24h; Ambient temperature;
  • 14
  • [ 617-86-7 ]
  • [ 7473-98-5 ]
  • 2-methyl-2-triethylsiloxypropiophenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tris(pentafluorophenyl)borate In dichloromethane for 20h; Ambient temperature;
42 %Spectr. With 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In neat (no solvent) at 50℃; for 12h; Glovebox; Inert atmosphere; Schlenk technique; chemoselective reaction;
  • 15
  • [ 67-56-1 ]
  • [ 7473-98-5 ]
  • [ 93-58-3 ]
YieldReaction ConditionsOperation in experiment
97 % Chromat. With oxygen at 20℃; for 5h;
  • 16
  • [ 7473-98-5 ]
  • [ 65-85-0 ]
YieldReaction ConditionsOperation in experiment
55% With oxygen; acetic acid In water at 60℃; for 12h;
100 % Chromat. With oxygen In water; acetic acid at 20℃; for 5h;
58 %Spectr. With C59H45BFeN6O3; oxygen In benzene at 20℃; for 0.366667h; Inert atmosphere;
  • 17
  • [ 7473-98-5 ]
  • Acrylic acid 11-[2,6-bis-(11-acryloyloxy-undecyloxy)-4-((S)-1-carboxy-ethylcarbamoyl)-phenoxy]-undecyl ester [ No CAS ]
  • acrylic acid 11-[2,6-bis-(11-acryloyloxy-undecyloxy)-4-(2-sulfo-ethylcarbamoyl)-phenoxy]-undecyl ester [ No CAS ]
  • polymer; Monomer(s): 3,4,5-[CH2=CHCOO(CH2)11-O]3}Ph-CO-NH-(CH2)2-SO3H; 3,4,5-[CH2=CHCOO(CH2)11-O]3}Ph-CO-NH-CH((S)-Me)COOH; 2-hydroxy-2-methylpropiophenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 20℃; for 24h; UV-irradiation;
  • 18
  • [ 7473-98-5 ]
  • Acrylic acid 11-[2,6-bis-(11-acryloyloxy-undecyloxy)-4-((S)-1-carboxy-ethylcarbamoyl)-phenoxy]-undecyl ester [ No CAS ]
  • acrylic acid 11-[2,6-bis-(11-acryloyloxy-undecyloxy)-4-(2-sulfo-ethylcarbamoyl)-phenoxy]-undecyl ester [ No CAS ]
  • polymer; Monomer(s): 3,4,5-[CH2=CHCOO(CH2)11-O]3}Ph-CO-NH-(CH2)2-SO3H; 3,4,5-[CH2=CHCOO(CH2)11-O]3}Ph-CO-NH-CH(Me)COOH; 2-hydroxy-2-methylpropiophenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With methanol In water at 20℃; for 24h; UV-irradiation;
  • 19
  • [ 108-86-1 ]
  • [ 7473-98-5 ]
  • [ 632-50-8 ]
YieldReaction ConditionsOperation in experiment
62 % Chromat. With palladium diacetate; caesium carbonate; triphenylphosphine In o-xylene for 20h; Heating;
  • 20
  • [ 108-86-1 ]
  • [ 7473-98-5 ]
  • [ 632-50-8 ]
  • 1,4,4-triphenyl-isochroman-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 9% 2: 79% With palladium diacetate; tri-tert-butyl phosphine; caesium carbonate In o-xylene for 6h; Heating;
  • 21
  • [ 106-38-7 ]
  • [ 7473-98-5 ]
  • [ 40673-57-2 ]
YieldReaction ConditionsOperation in experiment
78 % Chromat. With palladium diacetate; caesium carbonate; tricyclohexylphosphine In o-xylene for 6h; Heating;
  • 22
  • [ 7473-98-5 ]
  • [ 71057-10-8 ]
YieldReaction ConditionsOperation in experiment
89% With Nonafluorobutanesulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile at 95℃; for 9h;
  • 23
  • [ 7473-98-5 ]
  • [ 460-00-4 ]
  • [ 19422-37-8 ]
  • 7-fluoro-4,4-bis-(4-fluoro-phenyl)-1-phenyl-isochroman-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 71% 2: 5 % Chromat. With palladium diacetate; tri-tert-butyl phosphine; caesium carbonate In o-xylene for 6h; Heating;
  • 24
  • [ 7473-98-5 ]
  • [ 1079-66-9 ]
  • 2-[(diphenylphosphino)oxy]-2-methylpropiophenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h;
94% With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h;
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; 4.2. General procedure for the preparation of 2-thio-substituted benzothiazoles General procedure: To a stirred solution of alcohol (1 mmol), Et3N (1.2 equiv.) in dry CH2Cl2 (1 mL) was successively added chlorodiphenylphosphine (1.2 equiv.) at RT under N2 atmosphere. After 2 h, benzothiazole-2-thiol (0.5 equiv.) and camphorquinone (1 equiv.) were added to the mixture, respectively. After the mixture was stirred for 12 h, it was extracted with CH2Cl2/H2O. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by preparative TLC on silica gel (hexane/EtOAc = 10/1) to afford the desired product.
  • 25
  • [ 7473-98-5 ]
  • (S)-1-(4-methoxyphenyl)ethylamine [ No CAS ]
  • (αS)-2-methyl-(α-methyl-4-methoxybenzyl)amino-1-phenylpropan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: 2-hydroxy-2-methylpropiophenone; (S)-1-(4-methoxyphenyl)ethylamine With toluene-4-sulfonic acid In toluene Heating; Stage #2: With sodium tetrahydroborate; acetic acid In tetrahydrofuran at 0 - 20℃;
  • 26
  • [ 7473-98-5 ]
  • [ 28899-97-0 ]
  • [ 7476-46-2 ]
YieldReaction ConditionsOperation in experiment
92% With copper diacetate; dicyclohexylmethylamine In dichloromethane at 20℃; for 3h;
  • 27
  • [ 7473-98-5 ]
  • [ 170918-42-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid monohydrate / toluene / 24 h / Heating
  • 28
  • [ 7473-98-5 ]
  • [ 17231-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / -78 - 0 °C 2: 85percent m-chloroperbenzoic acid / CH2Cl2
  • 29
  • [ 732982-66-0 ]
  • [ 7473-98-5 ]
  • 3-(1(S)-(4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 3h; 1; 2 EXAMPLES 1 and 2 3- (1 (S)- (4-Chlorobenzyl)-2 (S)- ( (2-hydroxy-2-methyl-1-phenylpropyl) amino) propyl) benzonitrile (Diastereomer A) and 3- (S)-(4-Chlorobenzyl)-2 (S)-((2-hydroxy-2-methyl-1- phenylpropyl) amino) propyl) benzonitrile. (Diastereomer B) To a solution of 250 mg (0.877 mmol) of 3- (4-chlorophenyl)-2 (S) (3-cyanophenyl)-l (S) -methyl- propylamine in 3 mL of dichloroethane, 134, uL (0.88 mmol) of 2-hydroxy-2-methylpropiophenone and 280 mg (1.32 mmol) of sodium triacetoxyborohydride were added. After stirring for 3 hr, the reaction was quenched with water and the organic layer was removed with a pipet. This layer was purified by prep TLC using 50% EtOAc/hexane as an eluant to isolate 3- (1 (S)- (4-chlorobenzyl)-2 (S)- ( (2-hydroxy-2- methyl-l-phenylpropyl) amino) propyl) benzonitrile (diastereomer A) as a higher Rf isomer (LC-MS: m/e = 433 (M+1), 3.09 min) and 3- (S)-(4-Chlorobenzyl)-2 (S)-((2-hydroxy-2-methyl-1- phenylpropyl) amino) propyl) benzonitrile (diastereomer B) as a lower Rf isomer.
  • 30
  • [ 782470-21-7 ]
  • [ 7473-98-5 ]
  • 2-chloro-5-(piperidine-1-sulphonyl) benzoic acid 1,1-dimethyl-2-oxo-2-phenylethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With dmap; triethylamine In toluene for 16h; Heating / reflux; Alkaline aqueous solution; 35 Example 35; Synthesis of 2-Chloro-5-(piperidine-1-sulphonyl) benzoic Acid 1, 1-DIMETHYL-2-OXO-2- phenylethyl Ester To a solution of 2-chloro-5-(piperidine-1-sulphonyl) benzoyl chloride (80 mg, 0. 248 mmol) in anhydrous toluene (2 mL) was added triethylamine (38 P, L, 28 mg, 0.273 mmol), polystyrene-supported DMAP (17 mg of 1.46 MMOL/G, 0.0248 mmol), and 2- HYDROXY-2-METHYL-1-PHENYLPROPAN-1-ONE (38 L, 41 mg, 0.248 mmol). The mixture was heated to reflux. After 16 hours the cooled reaction mixture was filtered. The resin was washed with CH2C12. The filtrate was partitioned between saturated NAHC03 and CHZCLZ. The organic phase was dried (MgS04), filtered, and concentrated. Column chromatography (20% EtOAc/hexanes) provided 2-chloro-5- (piperidine-l- sulphonyl) benzoic acid 1, 1-DIMETHYL-2-OXO-2-PHENYLETHYL ester (20 mg, 18%) as a colourless oil. IH NMR (CDC13) 8 : 8. 02 (d, 2H), 7. 85 (d, 1H), 7.74 (dd, 1H), 7.56 (d, 1H), 7.50 (collapsed dd, 1H), 7.39 (collapsed dd, 2H), 2.92-2. 96 (t, 4H), 1.89 (s, 6H), 1. 58-1. 64 (m, 4H), 1.43-1. 45 (m, 2H).
  • 31
  • [ 7473-98-5 ]
  • [ 24647-09-4 ]
  • [ 402831-46-3 ]
YieldReaction ConditionsOperation in experiment
62% With pyridine In HCFC-225 at 5℃; for 5h;
  • 32
  • [ 7473-98-5 ]
  • [ 814-68-6 ]
  • [ 103658-85-1 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 2-hydroxy-2-methylpropiophenone With triethylamine In dichloromethane for 0.5h; Inert atmosphere; Stage #2: acryloyl chloride In dichloromethane for 19h; Inert atmosphere; 2-Methyl-1-oxo-1-phenylpropan-2-yl Acrylate (4) To a solution of 2-hydroxy-2-methylpropiophenone (5 mmol) in CH2Cl2 (50 mL) was added triethylamine (8 mmol) and stirred for 30 min. Then, acryloyl chloride (6 mmol) was added to the mixture and stirred for 19 h. The mixture was quenched with 10% HCl and extracted with CH2Cl2. The CH2Cl2 layer was washed with sat. NaCl and dried over MgSO4. The solvent was removed in vacuo to give a yellow solid. The solid was purified by recrystallization by hexane and was obtained in 83% (901 mg): A colorless solid; mp 91.0-92.0 °C; 1H-NMR (400 MHz, CDCl3) δ: 1.76 (6H, s), 5.80 (1H, dd, J=10.8,1.2 Hz), 6.05 (1H, dd, J=17.4, 10.8 Hz), 6.31 (1H, dd, J=17.4,1.2 Hz), 7.38 (2H, m), 7.48 (1H, m), 8.02 (2H, m); 13C-NMR (100 MHz, CDCl3) δ: 25.30, 84.31, 128.0, 128.2, 128.3, 131.4,132.2, 134.2, 164.8, 198.5; MS m/z: 218 (M+). HR-MS Calcd for C13H14O3: 218.094 (M+), Found: 218.094; IR (KBr) cm-1:1709, 1679.
With triethylamine In 1,4-dioxane; ice-water 1 Phenyl 2-acryloyloxy-2-propyl ketone EXAMPLE 1 Phenyl 2-acryloyloxy-2-propyl ketone To 5.0 g (0.03 mol) of commercially available phenyl 2-hydroxy-2.propyl ketone in 40 ml of dioxane are added under inert gas protection 5.4 g (0.06 mol) of acryloyl chloride and then, dropwise with stirring, a mixture of 6.1 g (0.06 mol) of triethylamine and 5 ml of dioxane. This is followed by refluxing for one hour and, after cooling down, discharge of the reaction mixture into 300 ml of ice-water. Extraction with ethyl acetate, removal of the solvent and recrystallization from methyl t-butyl ether gave 3.2 g of the photoinitiator with a melting point of 89° C.
With triethylamine In dichloromethane for 12.5h; Inert atmosphere; 1 S1. 20 parts of Darocurl 173 and 27 parts of triethylamine were dissolved in 40 parts of re-distilled dichloromethane solvent;S2 was added to a four-necked round bottom flask equipped with a thermometer, a ball condenser, a constant pressure funnel and a nitrogen tube in a nitrogen atmosphere, and placed in an ice bath to keep the agitated state. Then, 51 parts of acryloyl chloride was added dropwise with a constant pressure funnel, and the reaction was carried out for about 30 minutes. After 12 h, the reaction was stopped by TCL spot plate and the reaction was stopped.S3. After the reaction, the solution was washed three times. The washed solution was dried in a beaker containing anhydrous magnesium sulfate granules overnight and concentrated to give a crude product of yellow liquid.S4. The yellow liquid crude product was added to absolute ethanol and frozen in a refrigerator for 24 h to give the product as a white needle.
Stage #1: 2-hydroxy-2-methylpropiophenone With triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: acryloyl chloride In dichloromethane at 20℃; for 8h; Cooling with ice; 3.a (a) Add 2-hydroxy-2-methyl-phenylacetone-1 (1173) (16.42 g, 0.10 mol), triethylamine (10.81 g 0.11 mol), and 150 mL of dichloromethane to mechanical stirrer In a 500 ml three-necked flask with a constant pressure dropping funnel, the mixture was stirred at room temperature for 10 minutes.Then, a solution of acryloyl chloride (9.96 g, 0.12 mol) in 100 mL of dichloromethane was added dropwise to the three-necked flask under ice-cooling, and the ice bath was removed after 2 h was added, and the reaction was continued for 6 h at room temperature.After the reaction, the product was filtered, the filtrate was washed twice with deionized water, 1 mol·L-1 hydrochloric acid and 1 mol·L-1 aqueous sodium bicarbonate solution, and the organic layer was dried over anhydrous Na 2 SO 4 .After filtration, the solvent was distilled off under reduced pressure to obtain a crude product, which was then recrystallized with ethanol as a solvent to finally obtain an intermediate product 1173Ac.

  • 33
  • dibenzo-18-crown-6 (dibenzo[b,k]- 1,4,7,10,13,16-hexaoxacyclooctadecadiene) [ No CAS ]
  • [ 611-70-1 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In tetrachloromethane; toluene 2 EXAMPLE 2 EXAMPLE 2 A total of 44 g of sodium hydroxide in the form of pellets is added, within 40 hours, to a stirred mixture of 74.5 g of 1-phenyl-2-methyl-1-propanone, 75 ml of carbon tetrachloride, 150 ml of toluene and 1 g of dibenzo-18-crown-6 (dibenzo[b,k]- 1,4,7,10,13,16-hexaoxacyclooctadecadiene) at 15°. The working up is carried out in analogy to Example 1 and, after distillation, 65.3 g (78% of theory) of pure 1-phenyl-2-hydroxy-2-methyl-1-propanone are obtained.
  • 34
  • [ 5137-55-3 ]
  • [ 611-70-1 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In tetrachloromethane; toluene; EXAMPLE 3 A total of 44 g of granulated sodium hydroxide is introduced, within 20 hours, into a stirred mixture of 74.5 g of 1-phenyl-2-methyl-1-propanone, 75 ml of carbon tetrachloride, 150 ml of toluene and 25 ml of methyltrioctylammonium chloride at 15. After working up as described in Example 1 and purification by distillation, 62.1 g (74% of theory) of pure 1-phenyl-2-hydroxy-2-methyl-1-propanone are obtained.
  • 35
  • [ 10152-58-6 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
With oxygen In water at 100℃; for 48h; 3 A mixture of 56 mg (0.25 mmol) Pd-acetate and 90 mg (0.25 mmol) bathocuproin in 50 ml_ of water is stirred for 24 h at room temperature. Subsequently, 741 mg (5 mmol) of the epoxide obtained in example 1 are added. The reaction mixture is stirred at 100°C for 48 h under oxygen atmosphere. After evaporation, the residue is filtered over Alox and the crude product purified by chromatography (hexane : ethyl acetate 6:1), yielding 386 mg of the desired product.
  • 36
  • [ 20907-13-5 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hypochlorite; potassium bromide In water; toluene at 0 - 5℃; for 1.16667h; 2b A solution of 3.5 g (29.7 mmol) KBr in 50 ml water is added to a solution of 50 g (0.297 mol)of the diol obtained in part (a) in 300 ml of toluene. Then 0.9 g (5.76 mmol) TEMPO is added.The reddish suspension is cooled to 0°C. 160 ml of a 12 % solution of sodium hypochlorite(0.3 mol) is added with maintaining the internal temperature at 5°C or lower. The mixture issubsequently stirred for 1 h at 0-5°C and then allowed to separate for 10 min. 400 ml ofsodium dithionite solution (obtained from 30 g sodium dithionite (85%) and 400 ml of water)is added to the organic phase and stirred at 85°C for 1-2 h. The organic phase is againseparated and concentrated (rotavap). The crude product is then subjected to fractionaldistillation, yielding 42.5 g (87%) of the desired product as a colourless oil.
83% With tert.-butylhydroperoxide; tetrabutylammomium bromide In decane; benzene at 40℃; for 24h; Sealed tube; chemoselective reaction;
1562 g With bromine In dichloromethane at 20℃; Large scale; 1.1 oxidation of diol 4 into Hydroxyketone Product 1 Step one: to a solution of 1662 grams of diol 4 in 20 L of CH2Cl2 at room temperature was slowly added 1598 grams of Br2 (1 eq), the reaction mixture was stirred while maintaining the reaction system at room temperature, and acidic HBr gas released was absorbed by water. The reaction progress was monitored by TLC until the completion was detected. Water of equal volume was thus added, and organic layer was separated. The solvent was then recovered and the concentrated crude product was subjected to distillation under reduced pressure to yield 1562 grams of hydroxyketone 1 as colorless oil. Product 1 has the following spectroscopic characterization data: 1H-NMR (CDCl3, ppm): 8.01 (d, 2H), 7.56 (t, 1H), 7.46 (t, 2H), 4.12 (br, 1H), 1.61 (s, 6H); 13C-NMR (CDC13, ppm): 204.7, 133.8, 132.8, 129.6, 128.3, 76.3, 28.3.
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 1h; 6.11/12.2 Example 11 (95)-l-Ethyl-10, 10-dimethyl-9-phenyl-l,6,9,10, 13, 14-hexahydro-12H-5,15-(azeno)pyrazolo[4,3- i] [ 1 ,4,6]oxadiazacyclotetradecin-7(8H)-one Example 12 (9R)- 1 -Ethyl- 10, 10-dimethyl-9-phenyl- 1,6,9,10, 13,14-hexahydro- 12H-5, 15- (azeno)pyrazolo[4,3-i][l,4,6]oxadiazacyclotetradecin-7(8H)-one Step 2: 2-Hydroxy-2-methyl-l-phenylpropan-l-one Example 11 (95)-l-Ethyl-10, 10-dimethyl-9-phenyl-l,6,9,10, 13, 14-hexahydro-12H-5,15-(azeno)pyrazolo[4,3- i] [ 1 ,4,6]oxadiazacyclotetradecin-7(8H)-one Example 12 (9R)- 1 -Ethyl- 10, 10-dimethyl-9-phenyl- 1,6,9,10, 13,14-hexahydro- 12H-5, 15- (azeno)pyrazolo[4,3-i][l,4,6]oxadiazacyclotetradecin-7(8H)-one Step 2: 2-Hydroxy-2-methyl-l-phenylpropan-l-one IBX (30.3 g, 108 mmol) was added to a stirred mixture of 2-methyl-l- phenylpropane-1, 2-diol (9 g, 54.1 mmol) in MeCN (100 mL). After stirring for 1 h at 80°C, the resulting mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on Si02, eluted with petroleum ether/EtOAc (1 : 1) to give 2-hydroxy-2- methyl-l-phenylpropan-l-one. MS (EI) calc'd for Ci0Hi3O2 [M+H]+ 165, found 165; 1H MR (300 MHz, DMSO): δ 8.18-8.14 (m, 2 H), 7.60-7.55 (m, 1 H), 7.50-7.44 (m, 2 H), 5.70 (s, 1 H), 1.41 (s, 6 H).

  • 37
  • [ 7473-98-5 ]
  • [ 625-36-5 ]
  • [ 1159136-27-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at -10 - 40℃; for 72.5h; 3 Synthesis of 2-propenoic acid 1,1-dimethyl-2-oxo-2-phenylethyl ester (INI-6) 9.9 g (60 mmol) 2-hydroxy-2-methyl-1-phenyl-1-propanone (Darocur 1173) was dissolved in 60 ml tetrahydrofuran. 6.1 g (60 mmol) triethyl amine was added and the reaction mixture was cooled to -10°C. 7.6 g (60 mmol) 3-chloro-propionyl chloride was added while the temperature was kept below -5°C. The reaction was allowed to continue for 30 minutes at 0°C and for 72 hours at 40°C. The precipitated salts were removed by filtration and the solvent was evaporated under reduced pressure. 3-chloro-propionic acid 1,1-dimethyl-2-oxo-2-phenylethyl ester was purified by preparative column chromatography on a Prochrom LC80 column, using n.-hexane/ethyl acetate 80/20 as eluent at a flow rate of 150 ml/min and Kromasil 60A 10 micron as silica. 1 g of 3-chloro-propionic acid 1,1-dimethyl-2-oxo-2-phenylethyl ester was isolated.
  • 38
  • [ 7473-98-5 ]
  • [ 149-30-4 ]
  • 2-(benzo[d]thiazol-2-ylthio)-2-methyl-1-phenylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With 2,6-dimethyl-1,4-benzoquinone; phenyl diphenylphosphinite In toluene at 40℃; for 24h; Inert atmosphere;
42% With ethyl-2-azidoacetate; phenyl diphenylphosphinite In toluene at 40℃; for 24h;
  • 39
  • [ 7473-98-5 ]
  • [ 3282-30-2 ]
  • [ 1196070-16-2 ]
YieldReaction ConditionsOperation in experiment
82% With pyridine at 25℃; Inert atmosphere;
  • 40
  • [ 7473-98-5 ]
  • [ 108-24-7 ]
  • [ 7476-41-7 ]
YieldReaction ConditionsOperation in experiment
94% With pyridine at 20℃; Inert atmosphere;
85 %Spectr. With 1,1,7,7-tetramethyl-9-azajulolidine; triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; General Procedure for Substrate Scope Using TMAJ General procedure: To a solution of tertiary alcohol S4 (43.4 μmol) in CH2Cl2 (217.1 μL) were added 1.0 Msolution of TMAJ in CH2Cl2 (4.34 μL, 4.34 μmol), NEt3 (18.2 μL, 130 μmol) and Ac2O (8.21μL, 86.8 μmol) at room temperature. The reaction was monitored by TLC. When the reactionfinished, it was quenched with saturated aqueous solution of NH4Cl, and the mixture wasextracted with AcOEt (x3). The combined organic layers were dried over anhydrous MgSO4,filtered, and concentrated under reduced pressure. The residue was measured by 1H NMRwithout further purification, and the yield was determined by the integration ratio comparedwith pyrazine (3.48 mg, 43.4 μmol) as an internal standard.
  • 41
  • [ 7473-98-5 ]
  • [ 124-63-0 ]
  • [ 17231-17-3 ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
  • 42
  • [ 552-16-9 ]
  • [ 7473-98-5 ]
  • [ 901355-55-3 ]
YieldReaction ConditionsOperation in experiment
39% With phenyl diphenylphosphinite; diethylazodicarboxylate In toluene at 80℃; for 1h;
  • 43
  • [ 7473-98-5 ]
  • [ 934-34-9 ]
  • [ 1213228-90-0 ]
YieldReaction ConditionsOperation in experiment
50% With phenyl diphenylphosphinite; diethylazodicarboxylate In toluene at 80℃; for 1h;
  • 44
  • 2-(2’-vinyloxyethoxy)ethyl acrylate [ No CAS ]
  • [ 7473-98-5 ]
  • [ 1231708-03-4 ]
YieldReaction ConditionsOperation in experiment
With 2,6-di-tert-butyl-4-methyl-phenol at 50℃; for 16h; 1 The amount of the photoinitiator containing a hydroxyl group (= starting initiator) as specified in Table 3, was dissolved in the amount 2-(2-vinyloxyethoxy)ethyl acrylate (Ether-1), specified in Table 3. 1 mol % BHT, relative to 2-(2-vinyloxyethoxy)ethyl acrylate, was added, followed by the addition of 5 mol % of trifluoroacetic acid, relative to the hydroxyl containing photoinitiating moiety. The reaction was allowed to continue for the specified reaction time specified in Table 3 at 50°C. 25 g of the pretreated ion exchanger was added and the reaction mixture was stirred for 1 hour at room temperature. The ion exchanger was removed by filtration.
  • 45
  • [ 7473-98-5 ]
  • [ 1308332-51-5 ]
YieldReaction ConditionsOperation in experiment
33% With aluminum (III) chloride In chloroform at 4 - 20℃; for 12h; Inert atmosphere; 5 Example 5 Example 5 Step one: under nitrogen atmosphere 5 grams of Darocur 1173 (2-hydroxy-2-methyl-1-phenylpropan-1-one) was mixed with 24 grams of anhydrous AlCl3 in 100 mL of dry chloroform. Upon cooling to 4 °C 4.5 grams of paraformaldehyde powder was slowly added and the resultant mixture was stirred at room temperature for 12 hrs (note that HCl gas released from the reaction was neutralized by 2N NaOH solution). The mixture was poured into water, and the precipitate generated was dissolved by adding 2N HCl solution. The organic layer thus separated was collected, and the aqueous layer was extracted with ethyl acetate for three times. The combined chloroform and ethyl acetate layer was next dried over anhydrous Na2SO4, filtered, and concentrated. The residue was loaded onto silica gel column and eluted by mixtures of hexane/ethyl acetate (V/V = 15/1) to give the intermediate 1-(3-(chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-one as a light-yellow oil (33% yield).
  • 46
  • [ 7473-98-5 ]
  • [ 1399078-81-9 ]
  • [ 1308332-51-5 ]
  • [ 1399089-16-7 ]
  • [ 1399091-64-5 ]
  • [ 1399093-31-2 ]
YieldReaction ConditionsOperation in experiment
1: 77.4% 2: 11.7% 3: 2.6% 4: 3.1% 5: 4.9% With aluminum (III) chloride In chloroform at 0 - 60℃; for 26h; Inert atmosphere; 9 Example 9: chloroform. After the mixture was cooled to 0 °C, 480 grams of anhydrous AlCl3 and 55 grams of paraformaldehyde powder were successively added and the resultant mixture was vigorously stirred at 60 °C overnight for 14 hrs (note that HCl gas released from the reaction was neutralized by 2N NaOH solution). An additional portion of 55 grams of paraformaldehyde was added at this point and the reaction was stirred at this temperature for another 12 hrs. The mixture was cooled to room temperature, and under vigorous stirring poured into 3 L of water. The organic layer thus separated was collected, and the aqueous layer was extracted with 1 L of dichloromethane for three times. The combined chloroform and dichloromethane layer was next dried over anhydrous Na2SO4, filtered, and concentrated. The residue was loaded onto silica gel column and gradient eluted by mixtures of hexane/ethyl acetate (V/V = 15/1 to 12/1) to give the intermediate 1-(3-(chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-one as a light-yellow oil (77.4% yield), and four other by-products A-D (22.6% combined yield). Characterization data for compound A (11.7% yield): 1H NMR (CDCl3, ppm): 8.01 (s, 2H), 7.63 (s, 1H), 4.63 (s, 4H), 3.78 (s, 1H), 1.62 (s, 6H); 13C NMR (CDCl3, ppm): 203.7, 138.5, 135.0, 132.7, 129.7, 76.7, 45.2, 28.3; Compound B (2.6% yield): 1H NMR (CDCl3, ppm): 7.93 (s, 2H), 7.82 (s, 2H), 7.43 (s, 2H), 4.60 (s, 4H), 4.12 (s, 2H), 3.82 (s, 2H), 1.59 (s, 12H); Compound C (3.1% yield): 1H NMR (CDCl3, ppm): 7.89 (dd, 2H), 7.86 (s, 2H), 7.42-7.40 (m, 4H), 4.10 (s, 2H), 4.05 (s, 2H), 1.60 (s, 12H); 13C NMR (CDCl3, ppm): 204.7, 140.8, 134.2, 133.4, 130.1, 128.7, 127.8, 76.5, 41.5, 28.4; Compound D (4.9% yield): 1H NMR (CDCl3, ppm): 10.06 (s, 1H), 8.54 (s, 1H), 8.31 (d, 1H, J = 7.5 Hz), 8.06 (d, 1H, J = 7.6 Hz), 7.62 (dd, 1H, J = 7.5 Hz, J = 7.6 Hz), 3.89 (s, 1H), 1.61 (s, 6H); 13C NMR (CDCl3, ppm): 203.4, 191.9, 136.0, 135.5, 135.3, 132.6, 131.5, 128.9, 77.0, 27.9.
  • 47
  • [ 7473-98-5 ]
  • [ 61367-07-5 ]
  • C18H25NO3 [ No CAS ]
  • 49
  • [ 1603-79-8 ]
  • [ 75-16-1 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: phenylglyoxylic acid ethyl ester With n-butyllithium; trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Stage #2: methylmagnesium bromide In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; for 0.583333h;
  • 50
  • [ 89894-42-8 ]
  • [ 7473-98-5 ]
  • [ 1448620-95-8 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 1,2-dichlorovinyl phenyl ether With n-butyllithium In diethyl ether; hexane at -78 - -20℃; for 2h; Stage #2: 2-hydroxy-2-methylpropiophenone In diethyl ether; hexane at -78 - 20℃;
  • 51
  • [ 7473-98-5 ]
  • [ 1437789-93-9 ]
  • [ 1437789-95-1 ]
  • [ 1456507-13-3 ]
YieldReaction ConditionsOperation in experiment
1: 46.5% 2: 3.28% With sodium tris(acetoxy)borohydride; acetic acid In N,N-dimethyl-formamide at 60℃; 5 Step 5: hydroxy-2-methyl-1-phenylpropyl)amino)cyclohexyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one To a flask charged with 3-((lr,4r)-4-aminocyclohexyl)-lH-imidazo[4,5- b]pyridin-2(3H)-one (0.335 g, 1.442 mmol) were added DMF (5.77 mL), l-phenyl-2- hydroxy-2-methyl- 1 -propanone (commercially available from Sigma- Aldrich, Milwaukee, WI) (0.219 mL, 1.442 mmol), and AcOH (0.091 mL, 1.586 mmol) respectively. The resulting suspension was stirred for 15 minutes prior to the addition of sodium triacetoxyborohydride (0.61 1 g, 2.88 mmol). The resulting suspension was then stirred overnight at 60°C leading to formation of product along with significant reduced alcohol and starting amine still remaining. Additional ketone (2 eq) and sodium triacetoxyborohydride (0.61 1 g, 2.88 mmol) were added, and the resulting mixture was stirred at 60°C. After 2 hours of stirring, LC-MS indicated starting material consumption and additional product present. Water was added to the mixture which was then transferred to a separatory funnel and extracted with EtOAc (2x). The combined organic layers were dried with Na2S04, filtered, and dried under reduced pressure providing a residue. The residue was purified with a 25 g SNAP column (Biotage) ramping DCM:MeOH (90: 10) in DCM from 0 - 30%, then isocratic at 30% providing impurity elution, then ramping to 100% polar eluent to provide 3-((lr,4r)-4- ((2-hydroxy-2-methyl-l-phenylpropyl)amino)cyclohexyl)-lH-imidazo[4,5-b]pyridin- 2(3H)-one (0.255 g, 0.670 mmol, 46.5 % yield), m/z (ESI) 381.2 (M+H)+.
  • 52
  • [ 7473-98-5 ]
  • [ 1456507-49-5 ]
  • [ 1456507-51-9 ]
YieldReaction ConditionsOperation in experiment
84% With sodium tris(acetoxy)borohydride In acetic acid; 1,2-dichloro-ethane at 20℃; 3 Step 3: 2-methyl-1-phenyl-1-(((1r,4r)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)cyclohexyl)amino)propan-2-ol To 1 -phenyl-2-hydroxy-2-methyl- 1 -propanone (1 0.981 mmol) in DCE (4.671 mL) at room temperature was added AcOH (53.5 34 mmol) followed by (lr,4r)-4-(5-phenyl-l,3,4-oxadiazol-2-yl)cyclohexanamine (227 mg, 0.934 mmol). The resulting mixture was stirred at room temperature for 5 minutes, followed by the addition of sodium triacetoxyborohydride (495 mg, 2.336 mmol). The resulting mixture was stirred at room temperature for 4 hours and an additional 0.5 eq 1-phenyl- 2-hydroxy-2-methyl- 1 -propanone and 1 eq sodium triacetoxyborohydride were added. The mixture was stirred overnight at room temperature. The mixture was quenched with water, diluted with DCM, transferred to a separatory funnel and extracted with DCM (2x). The combined organic layers were dried with Na2S04, filtered, and concentrated under reduced pressure. The material thus obtained was purified with MPLC (0 to 70 to 90% 90/10 DCM-MeOH in DCM) providing product (308 mg, 84%). m/z (ESI) 392.4 (M+H)+.
  • 53
  • [ 50-00-0 ]
  • [ 7473-98-5 ]
  • [ 1308332-51-5 ]
YieldReaction ConditionsOperation in experiment
33% With aluminum (III) chloride In chloroform at 4 - 20℃; for 12h; Inert atmosphere; 5.1 Step one: under nitrogen atmosphere 5 grams of Darocur 1173 (2-hydroxy-2-methyl-1-phenylpropan-1-one) was mixed with 24 grams of anhydrous AlCl3 in 100 mL of dry chloroform. Upon cooling to 4° C. 4.5 grams of paraformaldehyde powder was slowly added and the resultant mixture was stirred at room temperature for 12 hrs (note that HCl gas released from the reaction was neutralized by 2N NaOH solution). The mixture was poured into water, and the precipitate generated was dissolved by adding 2N HCl solution. The organic layer thus separated was collected, and the aqueous layer was extracted with ethyl acetate for three times. The combined chloroform and ethyl acetate layer was next dried over anhydrous Na2SO4, filtered, and concentrated. The residue was loaded onto silica gel column and eluted by mixtures of hexane/ethyl acetate (V/V=15/1) to give the intermediate 1-(3-(chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-one as a light-yellow oil (33% yield).
  • 54
  • [ 50-00-0 ]
  • [ 7473-98-5 ]
  • [ 1399078-81-9 ]
  • [ 1308332-51-5 ]
  • [ 1399089-16-7 ]
  • [ 1399091-64-5 ]
  • [ 1399093-31-2 ]
YieldReaction ConditionsOperation in experiment
1: 77.4% 2: 11.7% 3: 2.6% 4: 3.1% 5: 4.9% With aluminum (III) chloride In chloroform at 0 - 60℃; for 26h; Inert atmosphere; 9 Under nitrogen atmosphere 100 grams of Darocur 1173 (2-hydroxy-2-methyl-1-phenylpropan-1-one) was placed in 2 L of dry chloroform. After the mixture was cooled to 0° C., 480 grams of anhydrous AlCl3 and 55 grams of paraformaldehyde powder were successively added and the resultant mixture was vigorously stirred at 60° C. overnight for 14 hrs (note that HCl gas released from the reaction was neutralized by 2N NaOH solution). An additional portion of 55 grams of paraformaldehyde was added at this point and the reaction was stirred at this temperature for another 12 hrs. The mixture was cooled to room temperature, and under vigorous stirring poured into 3 L of water. The organic layer thus separated was collected, and the aqueous layer was extracted with 1 L of dichloromethane for three times. The combined chloroform and dichloromethane layer was next dried over anhydrous Na2SO4, filtered, and concentrated. The residue was loaded onto silica gel column and gradient eluted by mixtures of hexane/ethyl acetate (V/V=15/1 to 12/1) to give the intermediate 1-(3-(chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-one as a light-yellow oil (77.4% yield), and four other by-products A-D (22.6% combined yield). Characterization data for compound A (11.7% yield): 1H NMR (CDCl3, ppm): 8.01 (s, 2H), 7.63 (s, 1H), 4.63 (s, 4H), 3.78 (s, 1H), 1.62 (s, 6H); 13C NMR (CDCl3, ppm): 203.7, 138.5, 135.0, 132.7, 129.7, 76.7, 45.2, 28.3; Compound B (2.6% yield): 1H NMR (CDCl3, ppm): 7.93 (s, 2H), 7.82 (s, 2H), 7.43 (s, 2H), 4.60 (s, 4H), 4.12 (s, 2H), 3.82 (s, 2H), 1.59 (s, 12H); Compound C (3.1% yield): 1H NMR (CDCl3, ppm): 7.89 (dd, 2H), 7.86 (s, 2H), 7.42-7.40 (m, 4H), 4.10 (s, 2H), 4.05 (s, 2H), 1.60 (s, 12H); 13C NMR (CDCl3, ppm): 204.7, 140.8, 134.2, 133.4, 130.1, 128.7, 127.8, 76.5, 41.5, 28.4; Compound D (4.9% yield): 1H NMR (CDCl3, ppm): 10.06 (s, 1H), 8.54 (s, 1H), 8.31 (d, 1H, J=7.5 Hz), 8.06 (d, 1H, J=7.6 Hz), 7.62 (dd, 1H, J=7.5 Hz, J=7.6 Hz), 3.89 (s, 1H), 1.61 (s, 6H); 13C NMR (CDCl3, ppm): 203.4, 191.9, 136.0, 135.5, 135.3, 132.6, 131.5, 128.9, 77.0, 27.9.
  • 55
  • [ 7473-98-5 ]
  • 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
  • (2-methyl-1-phenyl-2-(((trifluoromethyl)Thio)oxy)propan-1-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine In dichloromethane at 20℃; for 0.0833333h;
90% With triethylamine In dichloromethane at 20℃; for 0.0833333h; 20 Example 20 50mL egg-shaped flask was added N - saccharin trifluoromethylthio group 1 (110mg, 0.39mmol), 2- methyl-2-hydroxyphenyl acetone (50.0mg, 0.3mmol), 96μL triethylamine (0.69mmol), two chloride (5 mL), at room temperature for 5min.After completion of the reaction, the reaction solution rapidly by about 6 millimeters silica gel column, the column with the amount of methylene chloride and washed twice, and the combined organic liquid, spin dry to give trifluoromethyl - (2-benzoyl) isopropyl thio peroxide (72mg, 90% isolated yield).Purity by NMR identified greater than 95%.Trifluoromethyl - (2-benzoyl-yl) thio-isopropyl peroxy (2-Methyl-1-phenyl-2 - (((trifluoromethyl) Thio) Oxy) propan-1-One):
  • 56
  • [ 7473-98-5 ]
  • [ 75-36-5 ]
  • [ 7476-41-7 ]
YieldReaction ConditionsOperation in experiment
49% With pyridine at 0 - 100℃; for 0.0833333h;
  • 58
  • [ 7473-98-5 ]
  • [ 141-97-9 ]
  • [ 1373648-44-2 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate In ethanol Reflux; Compounds 5-8 (general procedure). General procedure: A solution of equimolar amounts of hydroxy ketone 1-4 and ethyl acetoacetate and 0.1 equiv of sodium ethoxide in anhydrous ethanol was heated under reflux. When the reaction was complete, a part of the solvent was distilled off, and the residue was neutralized with dilute (1 : 1) hydrochloric acid and extracted with methylene chloride.The organic phase was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was distilled under reduced pressure to isolate 3-acetyl-4,5,5-trimethylfuran-2(5H)-one (5) [5], 3-acetyl-5,5-dimethyl-4-phenylfuran-2(5H)-one (6) [7], 3-acetyl-4-methyl-5,5-pentamethylenefuran-2(5H)-one (7) [6], or 3-acetyl-5,5-pentamethylen-4-phenylfuran-2(5H)-one (8) [6].
  • 59
  • [ 70412-41-8 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 1-bromo-2-methyl-1-phenylpropan-2-ol With water at 100℃; for 1h; Stage #2: With dihydrogen peroxide for 6h; Cooling with ice; Irradiation; 1 Synthesis of 2-hydroxy-2-methyl-1-phenylpropan-1-one Next, 600 g of water was mixed with 162 g (0.7 mol) of 1-bromo-2-methyl-1-phenylpropan-2-ol. The mixture was stirred at 100° C. for 1 hour and then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). After extracted the crude product with DCE and brine and evaporated to remove the solvent, 2-hydroxy-2-methyl-1-phenylpropan-1-one was produced with a yield of 82%. (bp. 102-103° C./4 mmHg)
  • 60
  • [ 100-86-7 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen bromide; dihydrogen peroxide; In 1,2-dichloro-ethane; at 60℃; for 12h;Irradiation; 112 g (0.745 mol) of 2-methyl-1-phenylpropan-2-ol and 127 g (1.86 mol) of 50% hydrogen peroxide were mixed in 1000 g of DCE to form a mixture. 63 g (0.373 mol) of hydrobromic acid was slowly added to the mixture at 60 C., and then mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). After extracted the curde product with DCE and brine and evaporated to remove the solvent, 2-hydroxy-2-methyl-1-phenylpropan-1-one was obtained with a yield of 85%. (bp. 102-103 C./4 mmHg)
  • 61
  • [ 50-00-0 ]
  • [ 7473-98-5 ]
  • 4'-chloromethyl-2-hydroxy-2-methyl-1-phenyl-1-propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.6% With aluminum (III) chloride In 1,2-dichloro-ethane at 30 - 35℃; Large scale; 1 4' - chloro methyl -2 - hydroxy -2 - methyl -1 - phenyl -1 - propyl ketone preparation The enamel in the reactor input 2000L dichloroethane solution, stir, at room temperature by adding powdered aluminum trichloride 2028 kg (15244 µM), after adding, control the temperature in the kettle in the 30 - 35 °C, dropwise 2 - hydroxy -2 - methyl -1 - phenyl -1 - propyl ketone 500 kg (3049 µM), adding paraformaldehyde to 650 kg, in the 30 - 35 °C reaction 15 - 16 hours. After the completion of the reaction, the reaction solution is slowly added to the provided with a 1000 kg of 10% hydrochloric acid in, static delamination. The aqueous phase by evaporation of the, concentrated, filtered, make the AlCl3 · 6H2 O. The organic phase is evaporated dichloroethane, shall be 4' - chloro methyl -2 - hydroxy -2 - methyl -1 - phenyl -1 - propyl ketone, yield 85.6%.
  • 62
  • [ 611-69-8 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: rac-2-methyl-1-phenylpropan-1-ol With iodine; acetone In 1,4-dioxane at 20℃; for 0.0833333h; Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1,4-dioxane at 80℃; for 24h;
  • 63
  • [ 7473-98-5 ]
  • C10H11O2(1-)*Li(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran at -60℃; for 0.5h; 23 Example 23. Attempted Preparation of ComparativePAG, CPAG-6 In an attempt to synthesize the above compound starting with 1,1 -difluoro-2-oxo-2-(1 -adamantylamino)ethanesulfonyl fluoride (SM-2) and 2-hydroxy-2-methylpropiophenone (Sigma-Aldrich), using a procedure similar to the one described in the synthesis of CPAG-5 (reaction scheme below), no product was isolated. The conversion of target compound was low and the target compound seemed to have decomposed during the reaction and treatment. Peaks derived from difluoromethylsulfonic acid (decomposition product) were confirmed afier treatment (‘9F NMR: -100.2 and -108.70 ppm). The target PAG was not isolable even when the reaction condition were changed.
  • 64
  • [ 7473-98-5 ]
  • [ 1311403-44-7 ]
  • C18H15S(1+)*C12H11F2O6S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform at 23℃; for 12h; 3 Example 3:Synthesis of a salt represented by the formula (I-3) To the resulting solution containing the salt represented by the formula (I-3-c)3.4 parts of the compound represented by the formula (I-3-d)Followed by stirring at 23 ° C. for 12 hours. To the resulting mixture,10 parts of acetonitrile and 30 parts of ion exchanged water were added and the mixture was stirred at 23 ° C. for 30 minutes, separated, and the organic layer was taken out. 30 parts of ion exchanged water was added to the obtained organic layer, and the mixture was stirred at 23 ° C. for 30 minutes, separated, and the organic layer was taken out. This operation was repeated 5 times. The obtained organic layer was concentrated, 40 parts of tert-butyl methyl ether was added to the concentrated mass, stirred, and filtered to obtain 4.88 parts of a salt represented by the formula (I-3) .
  • 65
  • [ 75-86-5 ]
  • [ 108-90-7 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 2-hydroxy-2-methylpropanenitrile With 3,4-dihydro-2<i>H</i>-pyran In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: chlorobenzene With magnesium In tetrahydrofuran; diethyl ether at 20 - 70℃; for 2h; Cooling with ice; 2 Example 2 Preparation of 2-tetrahydropyranyl-2-methyl-propionitrile:40g of dihydropyran,1 g of macroporous strongly acidic ion exchange resin and 20 ml of tetrahydrofuran were added to a dry 100 ml flask, and 34 g (0.4 mol) of acetone cyanohydrin was added dropwise under nitrogen protection and stirring.After the completion of the dropwise addition, the reaction was further stirred at room temperature for 1 hour.After filtering out the strongly acidic ion exchange resin,The solvent and excess dihydropyran are removed under reduced pressure.The resulting 2-tetrahydropyranyl-2-methyl-propionitrile was used directly in the subsequent reaction.50 ml of a 2 M phenyl metal reagent solution prepared from chlorobenzene and magnesium metal in tetrahydrofuran was added to a 250 ml dry flask filled with nitrogen in an ice water bath.Under stirring,A solution of 18 g of 2-tetrahydropyranyl-2-methyl-propanenitrile in 20 ml of anhydrous diethyl ether was added dropwise.After the completion of the dropwise addition, the reaction was carried out at room temperature for 1 hour.The reaction was then refluxed at 60 to 70 ° C for 1 hour.The reaction solution was poured into a mixture of 100 ml of ice water and 12 g of concentrated sulfuric acid.The organic phase is isolated. Add 50 ml of 10w% sulfuric acid solution to the organic phase.The reaction was stirred at 40 ° C for 2 hours, and the organic phase was separated.Wash with sodium bicarbonate solution and deionized water until the pH is neutral,Dry with anhydrous sodium sulfate,After removing the solvent under reduced pressure, about 13.6 g of a colorless liquid product was obtained, and the yield is shown in Table 1.The 1H NMR spectrum is shown in Figure 2.
  • 66
  • [ 108-86-1 ]
  • [ 75-86-5 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 2-hydroxy-2-methylpropanenitrile With 3,4-dihydro-2<i>H</i>-pyran In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: bromobenzene With magnesium In tetrahydrofuran; diethyl ether at 20 - 70℃; for 2h; Cooling with ice; 2 Example 2 General procedure: Preparation of 2-tetrahydropyranyl-2-methyl-propionitrile:40g of dihydropyran,1 g of macroporous strongly acidic ion exchange resin and 20 ml of tetrahydrofuran were added to a dry 100 ml flask, and 34 g (0.4 mol) of acetone cyanohydrin was added dropwise under nitrogen protection and stirring.After the completion of the dropwise addition, the reaction was further stirred at room temperature for 1 hour.After filtering out the strongly acidic ion exchange resin,The solvent and excess dihydropyran are removed under reduced pressure.The resulting 2-tetrahydropyranyl-2-methyl-propionitrile was used directly in the subsequent reaction.50 ml of a 2 M phenyl metal reagent solution prepared from chlorobenzene and magnesium metal in tetrahydrofuran was added to a 250 ml dry flask filled with nitrogen in an ice water bath.Under stirring,A solution of 18 g of 2-tetrahydropyranyl-2-methyl-propanenitrile in 20 ml of anhydrous diethyl ether was added dropwise.After the completion of the dropwise addition, the reaction was carried out at room temperature for 1 hour.The reaction was then refluxed at 60 to 70 ° C for 1 hour.The reaction solution was poured into a mixture of 100 ml of ice water and 12 g of concentrated sulfuric acid.The organic phase is isolated. Add 50 ml of 10w% sulfuric acid solution to the organic phase.The reaction was stirred at 40 ° C for 2 hours, and the organic phase was separated.Wash with sodium bicarbonate solution and deionized water until the pH is neutral,Dry with anhydrous sodium sulfate,After removing the solvent under reduced pressure, about 13.6 g of a colorless liquid product was obtained, and the yield is shown in Table 1.The 1H NMR spectrum is shown in Figure 2.
  • 67
  • [ 67-68-5 ]
  • [ 611-70-1 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
85% With dipotassium peroxodisulfate; iodine at 120℃; for 8h;
85% With dipotassium peroxodisulfate; iodine at 120℃; for 8h;
  • 68
  • [ 7473-98-5 ]
  • [ 105-34-0 ]
  • 6,6-dimethyl-6a-phenyl-6,6a-dihydrofuro[3,4-d]oxazol-4(3aH)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 2-hydroxy-2-methylpropiophenone With C39H40N3O2P; silver(l) oxide In ethyl acetate at -20℃; for 0.5h; Molecular sieve; Inert atmosphere; Stage #2: methyl 2-cyanoacetate In ethyl acetate at -20℃; for 18h; Molecular sieve; Inert atmosphere; enantioselective reaction;
  • 69
  • [ 667-27-6 ]
  • [ 7473-98-5 ]
  • C14H16F2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; silver fluoride; triphenylphosphine In hexane at 140℃; for 20h; Sealed tube; Inert atmosphere; 23.1-23.3 In this embodiment, a preparation method of a benzoyl para-difluoroalkylated derivative is shown as follows: 2-hydroxy-2-methyl-1-phenyl-1-propanone is used as a raw material, and the reaction formula is as follows : (1) Adding 2-hydroxy-2-methyl-1-phenyl-1-propanone to the reaction tube, 0.0328 g (0.2 mmol), tetratriphenylPhenylphosphine palladium 0.0116 g (0.01 mmol), potassium acetate 0.0786 g (0.8 mmol), triphenylphosphine 0.0157 g (0.06 mmol), silver fluoride 0.0077 g (0.06 mmol), ethyl bromodifluoroacetate 0.0203 g (1.00 Methyl) and 0.25 mL of n-hexane, protected with argon and reacted at 140 ° C for 20 hours;(2) TLC tracks the reaction until it is completely over;(3) The crude product obtained after the completion of the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain a target.Product (yield 61%).
61% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; silver fluoride; triphenylphosphine In hexane at 140℃; for 20h; Inert atmosphere; Sealed tube;
  • 70
  • [ 7473-98-5 ]
  • [ 140-29-4 ]
  • [ 21994-87-6 ]
YieldReaction ConditionsOperation in experiment
88% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 71
  • [ 7473-98-5 ]
  • [ 140-29-4 ]
  • C18H16O(18)O [ No CAS ]
  • [ 21994-87-6 ]
YieldReaction ConditionsOperation in experiment
1: 87% 2: 13% With copper(l) iodide; <SUP>18</SUP>O-labeled water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 72
  • [ 459-22-3 ]
  • [ 7473-98-5 ]
  • 3-(4-fluorophenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 73
  • [ 7473-98-5 ]
  • [ 140-53-4 ]
  • 3-(4-chlorophenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 74
  • [ 16532-79-9 ]
  • [ 7473-98-5 ]
  • 3-(4-bromophenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 75
  • [ 51628-12-7 ]
  • [ 7473-98-5 ]
  • 3-(4-iodophenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
  • 76
  • [ 2947-61-7 ]
  • [ 7473-98-5 ]
  • 5,5-dimethyl-4-phenyl-3-(p-tolyl)furan-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 77
  • [ 3288-99-1 ]
  • [ 7473-98-5 ]
  • 3-(4-(tert-butyl)phenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
  • 78
  • [ 7473-98-5 ]
  • [ 104-47-2 ]
  • [ 83253-77-4 ]
YieldReaction ConditionsOperation in experiment
79% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 79
  • [ 7473-98-5 ]
  • [ 2338-75-2 ]
  • 5,5-dimethyl-4-phenyl-3-(4-(trifluoromethyl)phenyl)furan-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 80
  • [ 7473-98-5 ]
  • [ 555-21-5 ]
  • 5,5-dimethyl-3-(4-nitrophenyl)-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 81
  • [ 19924-43-7 ]
  • [ 7473-98-5 ]
  • [ 83253-77-4 ]
YieldReaction ConditionsOperation in experiment
88% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 82
  • [ 7473-98-5 ]
  • [ 7035-03-2 ]
  • 3-(2-methoxyphenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 83
  • [ 93-17-4 ]
  • [ 7473-98-5 ]
  • 3-(3,4-dimethoxyphenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 84
  • [ 7473-98-5 ]
  • [ 13388-75-5 ]
  • 3-(3,5-dimethoxyphenyl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 85
  • [ 7473-98-5 ]
  • [ 13338-63-1 ]
  • 5,5-dimethyl-4-phenyl-3-(3,4,5-trimethoxyphenyl)furan-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 86
  • [ 7473-98-5 ]
  • [ 4439-02-5 ]
  • 3-(benzo[d][1,3]dioxol-5-yl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 87
  • [ 7498-57-9 ]
  • [ 7473-98-5 ]
  • 5,5-dimethyl-3-(naphthalen-2-yl)-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 88
  • [ 2739-97-1 ]
  • [ 7473-98-5 ]
  • 5,5-dimethyl-4-phenyl-3-(pyridin-2-yl)furan-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 89
  • [ 20893-30-5 ]
  • [ 7473-98-5 ]
  • [ 83253-79-6 ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 90
  • [ 3216-48-6 ]
  • [ 7473-98-5 ]
  • 3-(benzo[b]thiophen-3-yl)-5,5-dimethyl-4-phenylfuran-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 91
  • [ 52407-43-9 ]
  • [ 7473-98-5 ]
  • C20H16O3 [ No CAS ]
  • 92
  • [ 7473-98-5 ]
  • [ 829-08-3 ]
YieldReaction ConditionsOperation in experiment
97% With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 20℃; for 12h;
  • 93
  • [ 201230-82-2 ]
  • [ 7473-98-5 ]
  • 1-cyclopropyl-1,3,3-trimethylurea [ No CAS ]
  • 2-methyl-1-oxo-1-phenylpropan-2-yl 4-(1,3,3-trimethylureido)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With di(rhodium)tetracarbonyl dichloride; tris(pentafluorophenyl)phosphine In 1,2-dichloro-benzene at 130℃; for 96h; Glovebox;
  • 94
  • [ 98-07-7 ]
  • [ 67-64-1 ]
  • [ 7473-98-5 ]
YieldReaction ConditionsOperation in experiment
82% With magnesium In N,N-dimethyl-formamide at -20 - -10℃; for 2h; Inert atmosphere; 2 2-hydroxy-2-methyl-1-phenylacetoneSynthesis Dissolve 12g of 80-100 mesh magnesium powder in 100ml DMF solvent, stir and cool down to -20 °C under nitrogen protection, dissolve 5.8g acetone and 23.46g trichloromethylbenzene in 40ml DMF solvent, slowly add to the first In the step system, the system temperature is maintained below -10 ° C for 2 hours, naturally warmed to room temperature, filtered, washed, and extracted with petroleum ether.Take, add 35% NaOH 17g aqueous solution and tetrabutylammonium bromide 0.15g, control the reaction temperature to 50 ° C for two hours, water washing, desolvent distillation to obtain the product 13.3g, purity 99.2%, yield 82%.
  • 95
  • [ 491-35-0 ]
  • [ 7473-98-5 ]
  • [ 37864-30-5 ]
YieldReaction ConditionsOperation in experiment
75% With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 12h; Irradiation;
  • 96
  • [ 7473-98-5 ]
  • [ 1204-28-0 ]
  • C19H14O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; (1) Add 6.56 g (0.04 mol) of 1173 photoinitiator and 4.50 (0.044 mol) of triethylamine to a three-necked flask,Dissolve in 100 ml of dichloromethane with magnetic stirring at room temperature. Reaction at room temperature,Dissolve 9.26 g (0.044 mol) of chlorinated metaphthalic anhydride in 40 ml of dichloromethane,Add a constant pressure dropping funnel,Slowly add to a three-necked flask.After the dropwise addition was completed, the reaction was stirred overnight,Filtered to remove triethylamine hydrochloride,The filtrate was washed three times with 50 ml of deionized water,The dried organic phase was purified again by column chromatography.The developing solvent of the corresponding silica gel column is a solvent mixed with petroleum ether and ethyl acetate.Its specific proportion is v (petroleum ether): v (ethyl acetate) = 2: 1,The obtained product was 11.0 g of a yellow liquid.
  • 97
  • [ 67-56-1 ]
  • [ 7473-98-5 ]
  • [ 1399093-31-2 ]
YieldReaction ConditionsOperation in experiment
With aluminum (III) chloride In chloroform at 60℃; for 26h; 1.1 (1) Add 0.1 mol of 2-hydroxy-2-methyl-1-phenyl-1-acetone and 0.1 mol of ketone to 50 mL of chloroform to dissolve it, and add 0.01 mol of aluminum chloride catalyst after it is fully dissolved, at 60°C After reacting for 26 hours, stop the reaction and spin-evaporate to obtain yellow crystals. The solid obtained after filtration, washing and recrystallization is vacuum dried, and finally purified by a chromatographic column to obtain 3-(2-hydroxy-2-methylpropionyl)benzaldehyde
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