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Product Details of [ 3160-40-5 ]

CAS No. :3160-40-5 MDL No. :MFCD00018790
Formula : C10H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :UUKRKWJGNHNTRG-NSCUHMNNSA-N
M.W : 180.63 Pubchem ID :736572
Synonyms :

Safety of [ 3160-40-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3160-40-5 ]

* 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 [ 3160-40-5 ]

[ 3160-40-5 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 3160-40-5 ]
  • [ 3506-75-0 ]
YieldReaction ConditionsOperation in experiment
97% With 1,4-dioxane; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(dicyclohexylphosphino)ethane at 130℃; for 10h; Inert atmosphere; Sealed tube; chemoselective reaction;
85% With methanol; C25H29ClNO2Rh; potassium carbonate at 90℃; for 1h; chemoselective reaction; 2.2. Transfer hydrogenation of unsaturated ketones in methanol A Radley tube was charged with an unsaturated ketone (0.3mmol), catalyst (0.003 mmol) and K2CO3 (0.25 eq), to which was introduced MeOH (1.5 mL). The reaction mixture was heated to reflux at 90 °C for 1 h. The resulting mixture was then cooled to room temperature, followed by solvent evaporation under vacuum. The product was purified by flash column chromatography (hexane/ethyl acetate, 4:1).
81% With formic acid; [Pd(C,N-2-chloro-7-(mesitylimidazolylidenylmethyl)naphthyridine)(η3-allyl)](BF4); triethylamine In isopropyl alcohol for 16h; Inert atmosphere; Reflux;
73% With bismuth(lll) trifluoromethanesulfonate; ammonium chloride; malononitrile In dichloromethane at 20℃; for 50h; regioselective reaction;
64.35% With palladium 10% on activated carbon; hydrogen In methanol for 3h; Preparation of substituted 4-Phenylbutan-2-ones General procedure: 4-Phenylbut-3-en-2-one (5 g) was dissolved in methanol (100 ml) and 10% Pd/C was added to it. The reaction mixture was shaken in a Parr shaker reactor under hydrogen pressure (30 psi) for 3 h. The reaction mixture was filtered over celite, washed with methanol (50 ml) and concentrated under reduced pressure. The crude product obtained was purified by column chromatography (Silica gel, 100-200 mesh, 9:1 hexane/ethyl acetate) to give the pure product.
With potassium hydroxide; palladium on activated charcoal Hydrogenation;
91 %Spectr. With bis(cyclopentadienyl)titanium dichloride; triethylamine hydrochloride; zinc In dichloromethane Inert atmosphere; chemoselective reaction;
With trichlorosilane; Triphenylphosphine oxide In 1,2-dichloro-ethane at 0℃; Inert atmosphere; chemoselective reaction;
With hydrogen In ethyl acetate for 2h; Inert atmosphere; 21.4 4-Chlorobenzylideneacetone (1 g, 5.5 mmol) was dissolved in EtOAc (10 mL) then platinum(rV) oxide (catalytic amount) was added. The mixture was purged with 2 (g) then H2 (g) then stirred under H2 atmosphere for 2 hours. The mixture was purged with 2 (g) then filtered to remove the catalyst. The crude material was purified on silica gel to yield the title compound.
With palladium 10% on activated carbon; hydrogen In dichloromethane at 20℃;
With D-glucose; ene-reductase P1-A04; glucose dehydrogenase-105; nicotinamide adenine dinucleotide phosphate In aq. buffer at 30℃; for 6h; Enzymatic reaction; stereoselective reaction;
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 1h; 4.1.2. General procedures for the preparation of compounds 8e01to 8-14 General procedure: To a solution of substituted benzaldehyde (80.6 mmol) inanhydrous acetone (100 mL), 1 M NaOH (80.6 mmol) in water wasadded. The reaction was stirred at room temperature for 2 h.Removal of the solvent gave a residue. H2O (300 mL) was added tothe residue. The mixture was extracted with EtOAc (3 50 mL),washed with brine, and dried over Na2SO4. The solvent wasremoved under reduced pressure to obtain compound 6. To a solutionof 3 in EtOAc, 10% Pd/C (0.1 equiv.) was added. The mixturewas stirred at room temperature for 1 h under 2 atm of hydrogen.The Pd/C was filtered and the solvent was removed to yield compound7. HCOONH4 was added to a solution of 7 and 10% Pd/C (0.1equiv.) in MeOH (100 mL). The reaction mixturewas heated to 75 Cfor 5 h. The mixture was cool to room temperature and the solventwas evaporated to yield a residue. H2O (100 mL) was added to theresidue. The mixturewas extracted with EtOAc (3 50 mL),washedwith brine, and dried over Na2SO4. The solvent was removed underreduced pressure to obtain compounds 8-01 to 8-14.

Reference: [1]Zhang, Deliang; Iwai, Tomohiro; Sawamura, Masaya [Organic Letters, 2019, vol. 21, # 15, p. 5867 - 5872]
[2]Aboo, Ahmed H.; Begum, Robina; Zhao, Liangliang; Farooqi, Zahoor H.; Xiao, Jianliang [Cuihua Xuebao/Chinese Journal of Catalysis, 2019, vol. 40, # 11, p. 1795 - 1799]
[3]Huang, Hsiao-Ching; Ramanathan, Mani; Liu, Yi-Hong; Peng, Shie-Ming; Liu, Shiuh-Tzung [Applied Organometallic Chemistry, 2017, vol. 31, # 8]
[4]Shang, Jun-Yan; Li, Fei; Bai, Xing-Feng; Jiang, Jian-Xiong; Yang, Ke-Fang; Lai, Guo-Qiao; Xu, Li-Wen [European Journal of Organic Chemistry, 2012, # 14, p. 2809 - 2815]
[5]Dhuru, Sameer; Bhedi, Dilip; Gophane, Dnyaneshwar; Hirbhagat, Kiran; Nadar, Vijaya; More, Dattatray; Parikh, Sapna; Dalal, Roda; Fonseca, Lyle C.; Kharas, Firuza; Vadnal, Prashant Y.; Vishwakarma, Ram A.; Sivaramakrishnan [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3784 - 3787]
[6]McQuillin; Ord [Journal of the Chemical Society, 1959, p. 2902,2906]
[7]Location in patent: scheme or table Ashfeld, Brandon L.; Kosal, Andrew D. [Organic Letters, 2010, vol. 12, # 1, p. 44 - 47]
[8]Cao, Jun-Jie; Zhou, Feng; Zhou, Jian [Angewandte Chemie - International Edition, 2010, vol. 49, # 29, p. 4976 - 4980]
[9]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2012/78593, 2012, A2 Location in patent: Page/Page column 149
[10]Cheng, Can; Ning, Xianling; Luo, Yongming; Tian, Chao; Wang, Xiaowei; Guo, Ying; Liu, Junyi; Zhang, Zhili [Medicinal Chemistry Research, 2016, vol. 25, # 8, p. 1678 - 1685]
[11]Martínez-Montero, Lía; Gotor, Vicente; Gotor-Fernández, Vicente; Lavandera, Iván [ACS Catalysis, 2018, vol. 8, # 3, p. 2413 - 2419]
[12]Xing, Gang; Zhi, Zhengxing; Yi, Ce; Zou, Jitian; Jing, Xuefeng; Yiu-Ho Woo, Anthony; Lin, Bin; Pan, Li; Zhang, Yuyang; Cheng, Maosheng [European Journal of Medicinal Chemistry, 2021, vol. 224]
  • 2
  • [ 104-88-1 ]
  • [ 67-64-1 ]
  • [ 3160-40-5 ]
YieldReaction ConditionsOperation in experiment
90% With nickel schiff-base complex doped in porous P2O5-SiO2 In lithium hydroxide monohydrate at 55℃; for 1.58333h; General Procedure for Aldol Condensation General procedure: In a typical reaction, benzaldehyde (1 mmol) and deionized water (5 mL) weremixed in a 25 cm3 glass batch. Subsequently, the catalyst powder (0.1 g) and acetophenone(1 mmol) were added to start the catalytic reaction. The progress of the reaction wasmonitored by TLC (eluent:ethyl acetate/n-hexane, 1:4). The catalyst was separated by asimple filtration and the product was obtained in high purity after evaporation of solvent.
89% With sodium hydroxide In lithium hydroxide monohydrate at 45℃; for 7h;
81% With L-lysine; lithium hydroxide monohydrate at 30 - 37℃; for 24h;
78% With graphene oxide In neat (no solvent) at 20℃; for 4h; General procedure for the aldol condensation General procedure: A reaction mixture containing aldehyde (1.2 mmol), acetophenone (1 mmol) and GO in water (0.5 mL) were stirred at room temperature for appropriate time. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with dichloromethane followed by subsequent separation of organic and aqueous layers by separating funnel. Organic layer was dried over Na2SO4 and concentrated under reduced pressure and obtained crude product was purified by column chromatography using EtOAc/hexane as eluent. All the yields were calculated from isolated products.
76% With N,N-dimethyl ammonium N,N-dimethyl carbamate In dichloromethane at 25℃; for 48h;
73% With piperidine; mesoporous silica In neat (no solvent) at 120℃; for 24h;
69% With sodium hydroxide In lithium hydroxide monohydrate at 20℃; for 3h;
68% With Fe3O4(at)L-proline/Pd2 NCs at 70℃; for 24h; Sealed tube;
53% With sodium hydroxide In lithium hydroxide monohydrate at 30℃; for 2.5h;
29.16% With sodium hydroxide In lithium hydroxide monohydrate at 0 - 20℃; General methods of Preparation of substituted 4-Phenylbut-3-en-2-ones General procedure: A solution of substituted benzaldehydes (50 mmol) in acetone (50 ml) was cooled to 0°C in an ice bath. To this a 10% aqueous NaOH solution was added dropwise and the reaction mixture was allowed to attain RT. It was then stirred at room temperature till the completion of the reaction. Acetone was removed under reduced pressure and the reaction was dissolved in ethyl acetate and washed with dilute HCl. The organic layer was separated wash twice with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel, 100-200 mesh, 9:1 hexane/ethyl acetate) to give the pure product.
With sodium hydroxide; ethanol
With sodium hydroxide
With sodium hydroxide at 20℃; for 2h;
Stage #1: 4-chlorobenzaldehyde; propan-2-one In lithium hydroxide monohydrate at 100℃; for 0.05h; Stage #2: With glacial acetic acid In lithium hydroxide monohydrate 30 Example 30 62.12 grams of acetone and 28.11 grams of 4-chlorobenzaldehyde were charged to a 100 ml autoclave fitted with a magnetic stirrer, nitrogen purge, cooling coil, temperature-controlled band heater, and blow case for introduction of reactants and catalysts under pressure. The blow case was charged with 0.65 grams of 25% aqueous sodium hydroxide solution and valved-off from the reactor vessel. These specifications gave a total feed of 5.3 moles of acetone per mole of 4-chlorobenzaldehyde and 0.02 moles caustic per mole of 4-chlorobenzaldehyde. The total amount of water present in the reaction mixture at the start of the reaction, based on the total weight of reactants, was thus about 0.53 wt. %. The autoclave was sealed, purged with nitrogen, and heated to 100° C., while stirring at 1800 rpm. Once a stable temperature had been reached the blow case was pressurized with nitrogen and the valve was opened to allow introduction of the blow case contents into the reaction vessel. The contents of the reactor were maintained at 100° C. and sampled three minutes after introduction of the caustic. The sample was cooled as collected, neutralized with acetic acid, and analyzed by gas chromatography. Conversion of 4-chlorobenzaldehyde was 99.7% at 95.7% selectivity to 1-(p-chlorophenyl)-1-buten-3-one. The calculated combined total amount of water in the reaction mixture at the end of the reaction, including both the amount of water provided at the start of the reaction, as well as the water of reaction created during the course of the reaction, was calculated to be 4.4 wt. %, based on the total weight of reactants
With hydroxide In ethanol
With sodium hydroxide In lithium hydroxide monohydrate
With potassium carbonate In methanol; lithium hydroxide monohydrate at 50 - 60℃; for 0.5h; Inert atmosphere;
With morpholin-4-ium 2,2,2-trifluoroacetate at 75℃; for 10h; Sealed vessel; 4.2. General procedure for the substituted benzylidenacetone General procedure: To a solution of aldehyde 6 (5 mmol) in acetone (12.5 mL) was added amine salt 7 (1 mmol, 201.14 mg). The reaction mixture was stirred at 75 °C in a sealed vial. After stirring at this temperature for 10 h, the reaction mixture was cooled to room temperature, saturated NaHCO3 solution and ethyl acetate was added. After phase separation the aqueous phase was extracted three times with ethyl acetate and the organic layer was dried over sodium sulfate and concentrated in vacuo to give mostly analytical pure products. If necessary the crude product was purified by column chromatography (ethyl acetate/hexane).
With sodium hydroxide In lithium hydroxide monohydrate at 40℃;
With sodium hydroxide In ethanol; lithium hydroxide monohydrate at 0 - 20℃; Inert atmosphere;
With morpholin-4-ium 2,2,2-trifluoroacetate
68 %Chromat. With carbon quantum dots at 20℃; for 24h; Irradiation;
89 %Chromat. With polystyrene resin supported piperazine In methanol at 110℃; for 0.333333h; Sealed tube; Microwave irradiation; Typical Procedure for Aldol Reaction Under MW Irradiation General procedure: Resin, aldehyde (0.5 mmol), solvent (4 mL), and finally ketone (1.0 mmol) were introduced to a 10-mL vessel. The vessel was sealed with a septum and placed into the microwave cavity. The microwave source was then turned on. After the time was up, HPLC or GC-MS were employed to determine the conversions and yields.
With Cs2CO3 In methanol at 20℃; for 4h;
In methanol at 20℃;
With Zr-Beta zeolite In toluene at 89.84℃; for 5h; Sealed tube;
With morpholin-4-ium 2,2,2-trifluoroacetate at 60℃; for 24h; Sealed tube;
With sodium hydroxide In lithium hydroxide monohydrate at 40℃;
In lithium hydroxide monohydrate at 20℃;
In ethanol; lithium hydroxide monohydrate at 20℃; for 0.0833333h; Inert atmosphere;
With sodium hydroxide In ethanol; lithium hydroxide monohydrate at 0 - 20℃;
With morpholin-4-ium 2,2,2-trifluoroacetate for 12h; Sealed tube; Heating;
With sodium hydroxide In lithium hydroxide monohydrate at 40℃; Inert atmosphere;
With sodium hydroxide In methanol at 20℃;
With sodium hydroxide In lithium hydroxide monohydrate at 45℃; for 7h;
With sodium hydroxide In lithium hydroxide monohydrate at 25℃; for 6h;
With sodium hydroxide In lithium hydroxide monohydrate at 20℃;
Stage #1: 4-chlorobenzaldehyde; propan-2-one With sodium lauryl sulfate In cyclohexane; lithium hydroxide monohydrate for 0.0333333h; Sonication; Stage #2: With sodium hydroxide In cyclohexane; lithium hydroxide monohydrate at 40℃; for 6h; Sealed tube;
With sodium hydroxide In ethanol; lithium hydroxide monohydrate at 0 - 20℃; 3.1A Condensation Procedure A Solid NaOH (0.356g, 8.89mmol,1.0eq) was dissolved in the mixture of acetone (2.63ml_, 35.57mmol, 4.0eq), water (12.5ml_) and EtOH (6.3mL). Then the 4-chlorobenzaldehyde (1.250g, 8.89mmol,1.0eq) was added dropwise within 20 min at 0 °C. The reaction mixture was allowed to warm to room temperature and was stirred until TLC analysis indicated completion of the reaction (0.5-2H). The reaction mixture was quenched with aqueous HCI (1 N), adjusted the pH to 6 and evaporated to remove the residual EtOH and acetone. The residue was extracted by EtOAc (3 c 40 ml_). The combined organic phases were washed with brine (50 ml_), dried over anhydrous Na2S04 and concentrated under reduced pressure. Crude product was purified by column chromatography on silica gel.
With sodium hydroxide In lithium hydroxide monohydrate at 20℃; for 2h; 4.1.2. General procedures for the preparation of compounds 8e01to 8-14 General procedure: To a solution of substituted benzaldehyde (80.6 mmol) inanhydrous acetone (100 mL), 1 M NaOH (80.6 mmol) in water wasadded. The reaction was stirred at room temperature for 2 h.Removal of the solvent gave a residue. H2O (300 mL) was added tothe residue. The mixture was extracted with EtOAc (3 50 mL),washed with brine, and dried over Na2SO4. The solvent wasremoved under reduced pressure to obtain compound 6. To a solutionof 3 in EtOAc, 10% Pd/C (0.1 equiv.) was added. The mixturewas stirred at room temperature for 1 h under 2 atm of hydrogen.The Pd/C was filtered and the solvent was removed to yield compound7. HCOONH4 was added to a solution of 7 and 10% Pd/C (0.1equiv.) in MeOH (100 mL). The reaction mixturewas heated to 75 Cfor 5 h. The mixture was cool to room temperature and the solventwas evaporated to yield a residue. H2O (100 mL) was added to theresidue. The mixturewas extracted with EtOAc (3 50 mL),washedwith brine, and dried over Na2SO4. The solvent was removed underreduced pressure to obtain compounds 8-01 to 8-14.
With potassium hydroxide In methanol; lithium hydroxide monohydrate at 0℃;
With sodium hydroxide In lithium hydroxide monohydrate at 25℃; for 1h;
With potassium hydroxide In methanol; lithium hydroxide monohydrate

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[3]Location in patent: scheme or table Zhang, Yan; Wang, Man Gang; Liang, Jun; Shang, Zhi Cai [Letters in Organic Chemistry, 2010, vol. 7, # 1, p. 27 - 31]
[4]Islam, Sk Manirul; Roy, Anupam Singha; Dey, Ram Chandra; Paul, Sumantra [Journal of Molecular Catalysis A: Chemical, 2014, vol. 394, p. 66 - 73]
[5]Location in patent: experimental part Mase, Nobuyuki; Kitagawa, Norihiko; Takabe, Kunihiko [Synlett, 2010, # 1, p. 93 - 96]
[6]Tanemura, Kiyoshi [Tetrahedron Letters, 2019, vol. 60, # 29, p. 1924 - 1928]
[7]Akai, Shuji; Hanada, Ryosuke; Fujiwara, Noboru; Kita, Yasuyuki; Egi, Masahiro [Organic Letters, 2010, vol. 12, # 21, p. 4900 - 4903]
[8]Tomer, Sanjiv O.; Soni, Hemant P. [Catalysis science and technology, 2019, vol. 9, # 22, p. 6517 - 6531]
[9]Al-Sabawi, Ammar H.; Saeed, Rana A. [Egyptian Journal of Chemistry, 2022, vol. 65, # 4, p. 129 - 133]
[10]Dhuru, Sameer; Bhedi, Dilip; Gophane, Dnyaneshwar; Hirbhagat, Kiran; Nadar, Vijaya; More, Dattatray; Parikh, Sapna; Dalal, Roda; Fonseca, Lyle C.; Kharas, Firuza; Vadnal, Prashant Y.; Vishwakarma, Ram A.; Sivaramakrishnan [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3784 - 3787]
[11]v. Walther; Raetze [Journal fur praktische Chemie (Leipzig 1954), 1902, vol. <2> 65, p. 279]
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[13]Dinakaran; Perumal [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 2, p. 135 - 136]
[14]Current Patent Assignee: EASTMAN CHEMICAL CO - US2005/4401, 2005, A1 Location in patent: Page 16; 17
[15]Location in patent: experimental part Oeztuerk, Goekce Sevim; Vural, Mert; Guenduez, Miyase Goezde; Simsek, Rahime; Sarioglu, Yusuf; Safak, Cihat [Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 12, p. 659 - 665]
[16]Location in patent: experimental part Prakash, Om; Sharma, Nitya; Ranjan, Pooja [Synthetic Communications, 2010, vol. 40, # 19, p. 2875 - 2879]
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[20]Liu, Yong; Kang, Tai-Ran; Liu, Quan-Zhong; Chen, Lian-Mei; Wang, Ya-Chuan; Liu, Jie; Xie, Yong-Mei; Yang, Jin-Liang; He, Long [Organic Letters, 2013, vol. 15, # 23, p. 6090 - 6093]
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  • 3
  • [ 3160-40-5 ]
  • [ 2652-77-9 ]
  • 4-<4-(4-Chlorphenyl)-3-buten-2-yliden>-2-diphenylpyrazolidin-3,5-dion [ No CAS ]
  • 4
  • [ 3160-40-5 ]
  • [ 53973-15-2 ]
YieldReaction ConditionsOperation in experiment
(i) Br2, AcOH, (ii) Na2CO3; Multistep reaction;
Multi-step reaction with 2 steps 1: bromine / dichloromethane / 0 °C 2: triethylamine / dichloromethane / 0 - 20 °C
Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With bromine In dichloromethane Stage #2: With triethylamine In dichloromethane
With bromine; triethylamine In diethyl ether; chloroform at 0 - 20℃;
Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With bromine In dichloromethane at 0℃; for 0.25h; Stage #2: With triethylamine In dichloromethane for 0.25h;
Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With bromine In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane for 0.25h; Inert atmosphere;

  • 5
  • [ 3160-40-5 ]
  • [ 1030268-24-6 ]
  • [ 54064-34-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane; water
  • 6
  • [ 3510-99-4 ]
  • [ 99-91-2 ]
  • [ 3160-40-5 ]
YieldReaction ConditionsOperation in experiment
59.3% With potassium <i>tert</i>-butylate In DMF (N,N-dimethyl-formamide) at 20℃; for 72h; 5 Preparation of E and Z enone isomers of 4-(4-chlorophenyl)-3-penten-2-one To a 500 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet and addition funnel were charged 10 g (0.065 moles) of 4'-chloroacetophenone, 10.2 g (0.065 moles) of ethyl-trans-3-ethoxycrotonate, and 150 mls of dry dimethylformamide. To this solution was then added 7.3 g (0.065 moles) of potassium t-butoxide in one portion. The reaction was stirred at ambient temperature under nitrogen for a total of three days. The reaction mixture was then poured into 200 mls of water and the aqueous was extracted with 3W50 mls of ethyl ether to remove any unreacted starting material. The aqueous fraction was acidified to pH 2 with 1 N aqueous HCl, and extracted with 3W100 mls of ethyl ether. The ether extract was washed with 2W100 mls of water and 100 mls of saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated on a rotary evaporator to afford 12.4 g of a tan solid. This solid was then stirred in 50 mls of conc. HCl for 2 hours at ambient temperature, then poured into 100 g of crushed ice, and extracted with 3W100 ml of ethyl ether. The ether extract was washed with 2W100 mls of water, 100 mls of brine, dried over anhydrous magnesium sulfate, filtered, and concentrated on a rotary evaporator to afford 7.6 g of a yellow liquid, 4-(4-chlorophenyl)-3-penten-2-one, which appeared to be a mixture of the E and Z enones, with some minor chemical impurities, in 59.3% crude yield. The product was used in the next step without further purification. 300 MHz 1H NMR (tms=0 ppm) 2.3 (s, 3H); 2.5 (s, 3H); 6.5 (s, 1H); 7.3-7.5 (m, 4H).
  • 7
  • [ 3160-40-5 ]
  • [ 1774-47-6 ]
  • cis-1-(4-chlorophenyl)-1-methyl-2-acetyl-cyclopropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
17.2% Stage #1: trimethylsulfoxonium iodide With sodium hydroxide In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one In dimethyl sulfoxide at 20℃; for 72h; 5 Preparation of trans and cis-1-(4-chlorophenyl)-1-methyl-2-acetylcyclopropane To a 250 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet and addition funnel were charged the trimethyl sulfoxonium iodide (8.5 g, 0.0386 moles), powdered sodium hydroxide (1.6 g, 0.0386 moles) and 100 mls of dry DMSO. The mixture was stirred at room temperature for 1 hour, followed by the rapid addition of the (E>Z)-4-(4-chlorophenyl)-3-penten-2-one (7.5 g, 0.0386 moles)) in 10 mls DMSO. The reaction was stirred for 3 days at ambient temperature, then poured into 200 mls of ice water and extracted with 3W100 ml of ethyl ether. The ether extract was washed with 2W100 mls of water, 100 mls of brine, dried over anhydrous MgSO4, filtered through 2 of silica gel, and concentrated on a rotary evaporator to afford 3.2 g of a thick pale yellow oil which was chromatographed on silica gel with 10% ethyl acetate, 90% hexane. The pure fractions were combined and concentrated on the rotary evaporator to afford 1.4 g (17.2% isolated yield) of a pale yellow liquid which was consistent with trans and cis-1-(4-chlorophenyl)-1-methyl-2-acetylcyclopropane upon analysis by 300 Mz 1H NMR. 300 MHz 1H NMR (tms=0 ppm) 1.2 (m, 1H); 1.4 (s, 3H); 1.6 (m, 1H); 2.2 (m, 1H); 2.35 (s, 3H); 7.1-7.4 (m, 4H).
  • 8
  • [ 3160-40-5 ]
  • [ 75-66-1 ]
  • [ 1115878-74-4 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With (R,R)-6,6'-bis-(1-hydroxy-2,2-dimethylpropyl)-2,2'-bipyridine; scandium tris(trifluoromethanesulfonate) In water at 30℃; for 0.166667h; Stage #2: 2-methylpropan-2-thiol With sodium hydroxide In water at 30℃; for 139h; optical yield given as %ee; enantioselective reaction;
70% Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With 2C13H17NO4*C20H27N3O In toluene at 20℃; for 0.166667h; Stage #2: 2-methylpropan-2-thiol In toluene at 20℃; for 116h; optical yield given as %ee; enantioselective reaction;
  • 9
  • [ 3160-40-5 ]
  • [ 79722-21-7 ]
  • [ 1088640-27-0 ]
YieldReaction ConditionsOperation in experiment
71% With 9-amino-9-deoxy-epi-cinchonidine; trifluoroacetic acid In toluene at 20 - 40℃; optical yield given as %ee;
  • 10
  • [ 3160-40-5 ]
  • [ 105-53-3 ]
  • [ 1056017-57-2 ]
YieldReaction ConditionsOperation in experiment
99% With (R,R)-1,2-diphenylethylenediamine; benzene-1,2-dicarboxylic acid In ethanol at 20℃; for 168h; enantioselective reaction;
95% With C27H37N5OS In tetrahydrofuran at 20℃; for 48h; optical yield given as %ee; enantioselective reaction;
  • 11
  • [ 3160-40-5 ]
  • [ 15014-25-2 ]
  • (R)-dibenzyl 2-(1-(4-chlorophenyl)-3-oxobutyl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With N-[(2S)-2-amino-3,3-dimethylbutyl]-4-methylbenzenesulfonamide In toluene at 20℃; for 72h; optical yield given as %ee; enantioselective reaction;
91% With (S)-3-(1H-indol-3-yl)-N1-propylpropane-1,2-diamine; trifluoroacetic acid In chloroform at 20℃; for 24h; optical yield given as %ee; enantioselective reaction;
  • 12
  • [ 3160-40-5 ]
  • 3-(4-chlorophenyl)-5-methylisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With p-toluenesulfonylhydroxylamine; potassium carbonate In methanol; water at 40℃; for 24h; Stage #2: With potassium carbonate In methanol; water at 60℃; for 10h; regiospecific reaction;
  • 13
  • [ 3160-40-5 ]
  • [ 1631-26-1 ]
  • [ 1195190-91-0 ]
YieldReaction ConditionsOperation in experiment
56% With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;
  • 14
  • [ 3160-40-5 ]
  • [ 2169-69-9 ]
  • [ 1195190-75-0 ]
YieldReaction ConditionsOperation in experiment
67% With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;
  • 15
  • [ 3160-40-5 ]
  • [ 2169-69-9 ]
  • [ 1195190-99-8 ]
YieldReaction ConditionsOperation in experiment
66% With ent-9-amino(9-deoxy)epi-hydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;
  • 16
  • [ 3160-40-5 ]
  • 2,6-dichloronitrostyrene [ No CAS ]
  • [ 1195190-68-1 ]
YieldReaction ConditionsOperation in experiment
92% With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; optical yield given as %de; enantioselective reaction;
  • 17
  • [ 3160-40-5 ]
  • [ 1076-38-6 ]
  • (R)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one [ No CAS ]
  • (S)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With (1R,2R)-1,2-cyclohexanediamine-MIL-4 In tetrahydrofuran at 10℃; for 96h; enantioselective reaction;
With succinic acid; C18H26N4O2; water In butan-1-ol at 40℃; for 12h; optical yield given as %ee;
With C36H30N2; trifluoroacetic acid In dichloromethane at 0℃; for 46h; optical yield given as %ee; enantioselective reaction;
77 % ee With 3-(5-((1S,2S)-2-amino-1,2-diphenylethylamino)-5-oxopentyl)-1-methyl-1H-imidazol-3-iumhexafluorophosphate; acetic acid In tetrahydrofuran at 20℃; Overall yield = 70 %; enantioselective reaction;
72 % ee With (S,S)-1,2-diphenyl-1,2-diaminoethane; benzoic acid In water at 20℃; for 10h; Sonication; Green chemistry; Overall yield = 89 %; enantioselective reaction; 1 (S)-3-[1-(4-Chlorophenyl)-3-oxobutyl]-4-hydroxy-chromen-2-one 3d General procedure: A suspension of 4-hydroxycoumarin 1 (81.0mg, 0.5mmol), α,β-unsaturated enone (0.6mmol), (S,S)-diphenylethylenediamine 9 as a catalyst (0.05mmol, 10mol%), an appropriate carboxylic acid (0.1mmol, 20mol%) and water (1mL) was sonicated at rt for 10h in an ultrasound bath. After extraction between EtOAc and water, the crude product was purified by column chromatography on silica gel (hexane-ethyl acetate, 4:1) to yield the pure product. The enantiomeric excess of the products was determined by HPLC using a chiral stationary phase. The Michael addition product was found to exist in rapid equilibrium with a pseudodiastereomeric hemiketal form in solution. However, the equilibrium was very rapid and therefore no pseudodiastereomers were observed during HPLC analysis. The equilibrium was slow enough that it showed up as a mixture of ketone and hemiketal by 1H NMR spectroscopy. The compound was isolated as a white solid. The enantiomeric excess was determined by HPLC analysis of the purified product with an Daicel AD-H column (hexane/i-PrOH, 4:1), 1.0mLmin-1, λ=254nm): tR=6.7min (minor) and tS=15.7min (major). Data for sample with 72% ee (S): [α]D23=+10.0 (c 1.0, acetonitrile), {Lit.12a [α]D25=-8.8 (c 0.28, acetonitrile), 79% ee (R)}; IR (KBr) 3377, 2984, 2934, 2855, 1686, 1608, 1565, 1490, 1385, 1377, 1071cm-1, 1H NMR (600MHz CDCl3): δ=9.47 (0.2H, s, OH, keto), 7.93 (0.2H, dd, 8.0 1.5Hz, ArH), 7.86 (0.7H, dd, J 8.0, 1.5Hz, ArH), 7.78 (1.0H, dd, J 8.2, 1.43Hz, ArH), 7.55 (0.7H, dt, J 8.7, 1.5Hz, ArH), 7.48-7.46 (1.3H, m, ArH), 7.33-7.13 (12.7H, m, ArH), 4.63 (0.2H, dd, J 10.4, 2.3Hz, CH, keto), 4.17 (0.7H, dd, J 6.8. 3.7Hz, CH, ketal), 4.13 (1.1H, dd, J 11.7, 6.8Hz, CH, ketal), 3.82 (0.2H, dd, J 19.3, 10.3Hz, CH2, keto), 3.44 (0.8H, br s, OH, ketal), 3.25 (0.2H, dd, J 19.3, 2.3Hz, CH2, keto), 3.11 (0.7H, br s, OH, ketal), 2.43 (1.8H, dd, J 14.1, 6.7Hz, CH2, ketal), 2.37 (0.7H, dd, J 14.2, 7.2Hz, CH2, ketal), 2.28 (0.7H, s, CH3, keto), 1.92 (1.1H, CH2, ketal), 1.72 (3.3H, s, CH3, ketal), 1.67 (2.1H, s, CH3, ketal); 13C NMR (150MHz, CDCl3): δ=161.9, 161.2, 159.6, 158.9, 152.9, 152.8, 152.8, 141.7, 140.5, 138.2, 132.5, 132.4, 132.1, 131.9, 131.7, 131.7, 129.4, 128.9, 128.7, 128.6, 128.4, 128.2, 123.9, 123.9, 123.7, 122.9, 122.7, 116.7, 116.5, 116.5, 116.5, 116.2, 115.7, 115.4, 107.5, 103.7, 101.2, 100.2, 98.9, 98.9, 45.1, 42.3, 39.8, 34.8, 34.1, 30.0, 28.2, 27.8, 26.8; m/z (EI) 342 (44, [M]+), 299 (100), 285 (16), 187 (24), 121 (39), 92 (13), 43 (37%); HRMS (EI): MH+, found 342.0668 C19H15O4Cl required 342.0659.
52 % ee With (S)-2-amino-N-((S)-1-hydroxy-4-methyl-1,1-diphenylpentan-2-yl)-4-methylpentanamide In tetrahydrofuran at 20℃; for 72h; Overall yield = 77 %; enantioselective reaction; General procedure for the asymmetric Michael reaction of 4-hydroxycoumarines 1, 8a-d to α,β-unsaturated ketones 2, 9a-h General procedure: 4-Hydroxycoumarines 1, 8a-d (0.1 mmol), α,β-unsaturated ketones 2, 9a-h (0.12 mmol), amino amide alcohol catalysts 7a-o (0.02 mmol) with/without additives (0.02 mmol) were stirred in THF (0.8 mL) at room temperature for the times shown in the Table 1. The reaction mixture was directly purified by preparative TLC on silica gel (hexane : AcOEt = 3 : 1) to afford warfarin 3 and its analogs 10a-l. Alladducts were known compounds and were identified by spectral data (1H and 13C-NMR) which were in good agreement with those reported.The enantiomeric excess (ee) were determined by HPLC (DAICELCHIRALPAK AD-H, 1.0 mL/min, n-hexane : 2-propanol = 80 : 20)
84 % ee With (S)-Mandelic acid; (1R,2R)-1,2-di(quinolin-8-yl)ethane-1,2-diamine In water at 50℃; for 24h; Green chemistry; Overall yield = 67 %; enantioselective reaction;
85 % ee With (R)-Mandelic Acid; (1S,2S)-1,2-di(quinolin-8-yl)ethane-1,2-diamine In water at 50℃; for 24h; Green chemistry; Overall yield = 65 %; Overall yield = 133 mg; enantioselective reaction;
88 % ee With (S,S)-4,4'-(((1S,2S)-1,2-di(pyridin-2-yl)ethane-1,2-diyl)bis(azanediyl))bis(3-(((1S,2S)-2-amino-1,2-diphenylethyl)amino)cyclobut-3-ene-1,2-dione); acetic acid In dichloromethane at 20℃; for 24h; Overall yield = 91 %; Overall yield = 39 mg; enantioselective reaction;

  • 18
  • [ 3160-40-5 ]
  • [ 134747-46-9 ]
YieldReaction ConditionsOperation in experiment
88% With sodium tetrahydroborate In methanol at 20℃; for 1h;
72% With 12C6H7N2S(1-)*20Cu(1+)*8I(1-); isopropyl alcohol; sodium hydroxide In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere; chemoselective reaction;
With C35H46Cl2N2O3P2RuSi; hydrogen; potassium hydroxide In isopropyl alcohol at 35℃; regioselective reaction;
With sodium tetrahydroborate
With sodium tetrahydroborate
With sodium tetrahydroborate; cerium(III) chloride In methanol at 0 - 20℃; for 1h; Inert atmosphere;

  • 19
  • [ 3160-40-5 ]
  • [ 626-35-7 ]
  • ethyl 3-(4-chlorophenyl)-2-nitro-5-oxohexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 9-amino-9-deoxyepicinchonine In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 24h; optical yield given as %de;
  • 20
  • [ 3160-40-5 ]
  • [ 79-46-9 ]
  • (S)-4-(4-chlorophenyl)-5-methyl-5-nitrohexan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With 4-nitro-phenol; C15H23N3 In dichloromethane at 20℃; for 24h; optical yield given as %ee; enantioselective reaction;
96% With C19H30N2; <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine In chloroform at 25℃; for 48h; enantioselective reaction;
  • 21
  • [ 3160-40-5 ]
  • [ 90-44-8 ]
  • [ 1236557-00-8 ]
YieldReaction ConditionsOperation in experiment
97% With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 20℃; for 72h; optical yield given as %ee; enantioselective reaction;
  • 22
  • [ 3160-40-5 ]
  • [ 1195737-74-6 ]
  • [ 1258422-84-2 ]
YieldReaction ConditionsOperation in experiment
99% With trifluoroacetic acid; 9-amino-9-deoxyepicinchonine In 1,4-dioxane at 20℃; for 72h; optical yield given as %ee; enantioselective reaction;
  • 23
  • [ 3160-40-5 ]
  • [ 124043-91-0 ]
  • [ 1258422-96-6 ]
YieldReaction ConditionsOperation in experiment
99% With trifluoroacetic acid; 9-amino-9-deoxyepicinchonine In 1,4-dioxane at 20℃; for 72h; optical yield given as %ee; enantioselective reaction;
  • 24
  • [ 3160-40-5 ]
  • [ 24526-69-0 ]
  • [ 1260430-23-6 ]
YieldReaction ConditionsOperation in experiment
86% With 9-epi-9-amino-9-deoxyquinine In dichloromethane at 25℃; for 96h; optical yield given as %ee; enantioselective reaction;
  • 25
  • [ 3160-40-5 ]
  • [ 3620-16-4 ]
  • [ 1262896-35-4 ]
  • [ 1262896-23-0 ]
YieldReaction ConditionsOperation in experiment
With 9-amino-9-deoxyepicinchonine; 4-nitro-benzoic acid In toluene at 20℃; for 36h; optical yield given as %ee; enantioselective reaction; 4.2. General procedure for the synthesis of compound 4a General procedure: To a solution of 2a (58 mg, 0.4 mmol) and 3 (67 mg, 0.44 mmol) in 2 mL toluene, 1b (12 mg, 0.04 mmol, 10 mol %) and PNBA (7 mg, 0.04 mmol, 10 mol %) were added. The mixture was stirred at room temperature and monitored by TLC. After completion (24 h), the mixture was concentrated by rotary evaporation and the residue was purified by flash chromatography (dichloromethane/pet. ether: 1/1) to provide 4a as a mixture of two isomers, 107 mg, 90%, then the mixture was further purified by flash chromatography (ethyl acetate/pet. ether: 1/4) to provide pure (2S,3R)-4a 71 mg as colorless oil and (2R,3R)-4a 36 mg as colorless oil.
  • 26
  • [ 3160-40-5 ]
  • (E)-4-(4-chlorophenyl)but-3-en-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With sodium tetrahydroborate In methanol at 0℃; for 0.666667h;
  • 27
  • [ 3160-40-5 ]
  • [ 3620-16-4 ]
  • [ 1293293-00-1 ]
YieldReaction ConditionsOperation in experiment
80% With N,N-dimethylethylenediamine; 4-nitro-benzoic acid In dichloromethane at 20℃; Inert atmosphere; 4.3. General procedure for the preparation of ketoester (3) General procedure: A solution of α,β-unsaturated methyl ketones (2) (0.1 mmol), fluoronitroacetates (1) (0.15 mmol), N',N'-dimethylethane-1,2-diamine (4) (20 mol %) and 4-nitrobenzoic acid (20 mol %) in CH2Cl2 (1.0 mL) was reacted at room temperture for appropriate times. After removal of the solvent under reduced pressure, the crude product was purified directly by column chromatography on silica gel (hexanes/EtOAc=5/1) to afford the desired products.
  • 28
  • [ 3160-40-5 ]
  • [ 1076-38-6 ]
  • C19H15ClO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-benzylthiourea In 1,4-dioxane at 25℃; for 55h; optical yield given as %ee; enantioselective reaction; 2. Asymmetric Michael addition of 1,3-dicarbonyl compounds to α,β-unsaturated ketones General procedure: 2 (32.4 mg, 0.2 mmol), 3 (35.0 mg, 0.24 mmol) and 1h (14.5 mg, 0.04 mmol) were stirred in 1,4-dioxane (1.5 mL) at 25 °C for 55 h. The mixture was separated by silica gel (20% ethyl acetate/petroleum ether) gave 4. The Michael addition product was found to exist in rapid equilibrium with a pseudo-diastereomeric hemiketal form in solution. The optical resolution is changeable in related to concentration and solvent, therefore, only the optical rotation of 4a was measured. All products are known compounds and were identified by spectroscopic data (MS, 1H and 13C NMR) which are in good agreement with those reported.[1,2] However, the equilibrium is very rapid and therefore no pseudo-diastereomers were observed during HPLC analysis using the mixture of hexane/ 2-propanol containing 0.1% TFA as the eluent [2a]. Daicel Chiralcel AD-H; 2-propanol/n-hexane, 20:80, containing 0.1% TFA; flow rate = 1.0 mLmin-1; λ = 220 nm.
  • 29
  • [ 3160-40-5 ]
  • [ 2945-08-6 ]
  • [ 1300627-69-3 ]
YieldReaction ConditionsOperation in experiment
88% With pyrrolidine; In dichloromethane; at 20℃; for 48h; General procedure: To a solution of alpha,beta-unsaturated ketones 3 (0.30 mmol) in CH2Cl2 (0.6 mL) at room temperature was added pyrrolidine (0.060 mmol) followed by addition of 2-arylacetate or 2-arylacetonitrile 2 (0.45 mmol). The resulting solution was stirred at room temperature until complete consumption of alpha,beta-unsaturated ketones 3 was observed as determined by TLC. The resulting mixture was direct purified by silica gel chromatography to afford desired compounds 4 and 5.
  • 30
  • [ 3160-40-5 ]
  • [ 557-20-0 ]
  • 4-(p-chloro-phenyl)-hexan-2-one [ No CAS ]
  • 4-(p-chloro-phenyl)-hexan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 1,4-bis(2-((S)-4-phenyl-4,5-dihydrooxazol-2-yl)propan-2-yl)phthalazine In diethyl ether; hexane; dichloromethane at -30℃; for 18h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; General procedure for Cu-catalyzed enantioselective conjugate addition The flame dried Schlenk tube was charged with Cu(MeCN)4BF4 (3.2 mg, 0.01 mmol) and one equivalent of ligand (0.01 mmol) under a N2 atmosphere and then the mixture was dissolved in dry dichloromethane (1.0 mL). The solution was stirred at 25 oC for 1 h, then substrate 5a~n and dry Et2O (1.0 mL) were added. The reaction turned to light yellow and some solid turned out. The solid dissolved after stirred for several minutes. Then the mixture was cooled to -30 oC and diethylzinc (1.0 mmol, 1.0 mL of 1M in hexane) was added dropwise within 1 h. The reaction mixture was stirred at -30 oC for 18 h. The mixture was quenched by saturated NH4Cl and extracted with CH2Cl2 (3×5 mL). The combined organic layers were dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 100/1 to 50/1) to afford the 1,4-addition product.
  • 31
  • [ 3160-40-5 ]
  • [ 100-53-8 ]
  • (R)-4-(benzylthio)-4-(4-chlorophenyl)butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With pyridine; (S, S)-6,6’-bis(1-hydroxy-2,2-dimethylpropyl)-2,2’-bipyridine; scandium tris(trifluoromethanesulfonate) In water at 20℃; for 24h; optical yield given as %ee; enantioselective reaction;
82% With pyridine; water; (S, S)-6,6’-bis(1-hydroxy-2,2-dimethylpropyl)-2,2’-bipyridine; scandium tris(trifluoromethanesulfonate) at 20℃; for 24h; optical yield given as %ee; enantioselective reaction;
  • 32
  • [ 3160-40-5 ]
  • [ 1679-07-8 ]
  • [ 1286762-15-9 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With (R,R)-6,6'-bis-(1-hydroxy-2,2-dimethylpropyl)-2,2'-bipyridine; scandium tris(trifluoromethanesulfonate) In water at 30℃; for 0.166667h; Stage #2: cyclopentylthiol With sodium hydroxide In water at 30℃; for 120h; optical yield given as %ee; enantioselective reaction;
  • 33
  • [ 3160-40-5 ]
  • [ 100-53-8 ]
  • [ 1115878-59-5 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With (R,R)-6,6'-bis-(1-hydroxy-2,2-dimethylpropyl)-2,2'-bipyridine; scandium tris(trifluoromethanesulfonate) In water at 30℃; for 0.166667h; Stage #2: phenylmethanethiol With sodium hydroxide In water at 30℃; for 24h; optical yield given as %ee; enantioselective reaction;
  • 34
  • [ 3160-40-5 ]
  • [ 108-59-8 ]
  • [ 1339109-10-2 ]
YieldReaction ConditionsOperation in experiment
93% With Rasta resin-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene at 60℃; for 15h; 2.3. General procedure for the Michael addition of dimethylmalonate (9) to α,β-unsaturated ketones 10a-c for the preparation of 11a-c General procedure. In a screw-capped vial equipped with a magnetic stirrer, Rasta-TBD (7a) (0.134 g, 0.4 mmol, 2.98 mmol/g), ketone 10 (2.0 mmol), and dimethylmalonate (9) (2.0 mmol) were consecutively added and the resulting mixture was left under vigorous stirring at 60 °C. After 15 h, ethyl acetate was added, the catalyst was recovered by filtration, and the organic solvent was evaporated under vacuum to give pure product 11 in 92-97% yield (see Section 3).
77% With potassium carbonate at 23℃; for 17h; Inert atmosphere;
Stage #1: malonic acid dimethyl ester With lithium hydroxide In methanol at 20℃; for 0.25h; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one In methanol at 20℃; for 40h;
  • 35
  • [ 3160-40-5 ]
  • [ 6623-89-8 ]
  • [ 1332338-96-1 ]
YieldReaction ConditionsOperation in experiment
92% With C20H25N3O; (R)-1,1'-binaphthyl-2,2'-phosphoric acid In 1,2-dichloro-ethane at 80℃; for 2.5h; optical yield given as %ee; enantioselective reaction;
  • 36
  • [ 3160-40-5 ]
  • [ 17629-27-5 ]
YieldReaction ConditionsOperation in experiment
94% With tetrabutylammomium bromide; toluene-4-sulfonic acid hydrazide; sodium hydroxide In water at 80℃; for 10h; Air atmosphere; 4.3. General procedure for the substituted benzylidenacetone General procedure: A Schlenk tube with a magnetic stir bar charged with α,β-unsaturated carbonyl compounds (0.5 mmol, 1 equiv), tosyl hydrazide (0.6 mmol, 1.2 equiv), NaOH (1.5 equiv), (n-Bu)4NBr (1.5 equiv). The reaction vessel was placed in an 80 °C oil bath, and then stirring at this temperature for 10 h. The reaction mixture was then allowed to cool to ambient temperature, and diluted with 20 mL of ethyl acetate, and washed with brine (15 mL), water (15 mL), and then the organic layer was dried over Na2SO4. After concentrated in vacuo, the crude product was purified by column chromatography. The identity and purity of the known product was confirmed by 1H NMR, 13C NMR, and GC-MS.
Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With toluene-4-sulfonic acid hydrazide In acetonitrile at 20℃; for 3h; Stage #2: With sodium hydroxide In acetonitrile at 60 - 70℃; for 12h;
  • 37
  • [ 3160-40-5 ]
  • [ 75-52-5 ]
  • (±)-4-(4-chlorophenyl)-5-nitropentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With Rasta resin-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene at 60℃; for 4h; 2.4. General procedure for the Michael addition of nitroalkanes 12a-c to α,β-unsaturated ketones 10a-c for the preparation of 13-21 General procedure. In a screw-capped vial equipped with a magnetic stirrer, Rasta-TBD (7a) (0.134 g, 0.4 mmol, 2.98 mmol/g), ketone 10 (2.0 mmol), and nitroalkane 12 (2.0 mmol) were consecutively added and the resulting mixture was left under vigorous stirring at 30 or 60 °C. After 3-30 h, ethyl acetate was added, the catalyst was recovered by filtration, and the organic solvent was evaporated under vacuum. The reaction mixture was purified by silica gel column chromatography (95/5 Petroleum ether/EtOAc, 100/1 silica/sample) to give the corresponding pure product (13-21) in 80-95% yield (see Section 3).
  • 38
  • [ 3160-40-5 ]
  • [ 79-46-9 ]
  • [ 1021184-66-6 ]
YieldReaction ConditionsOperation in experiment
95% With Rasta resin-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene at 60℃; for 24h; 2.4. General procedure for the Michael addition of nitroalkanes 12a-c to α,β-unsaturated ketones 10a-c for the preparation of 13-21 General procedure. In a screw-capped vial equipped with a magnetic stirrer, Rasta-TBD (7a) (0.134 g, 0.4 mmol, 2.98 mmol/g), ketone 10 (2.0 mmol), and nitroalkane 12 (2.0 mmol) were consecutively added and the resulting mixture was left under vigorous stirring at 30 or 60 °C. After 3-30 h, ethyl acetate was added, the catalyst was recovered by filtration, and the organic solvent was evaporated under vacuum. The reaction mixture was purified by silica gel column chromatography (95/5 Petroleum ether/EtOAc, 100/1 silica/sample) to give the corresponding pure product (13-21) in 80-95% yield (see Section 3).
  • 39
  • [ 3160-40-5 ]
  • [ 106-45-6 ]
  • [ 1346911-70-3 ]
YieldReaction ConditionsOperation in experiment
89% With [ReOCl3(OPPh3)(SMe2)] In ethyl acetate at 20℃; General procedure for addition of thiol to enones: General procedure: At room temperature under an ambient atmosphere, EtOAc (2.0 mL, 2.0 M) was added to a scintillation vial containing thiol (1.2 mmol, 1.2 equiv). Enone (1 mmol, 1 equiv) then Re(O)Cl3(SMe2)(OPPh3) (13.0 mg, 0.02 mmol, 0.02 equiv) were added to the solution. The reaction solution was stirred at room temperature and monitored by TLC. Upon completion, the reaction was quenched by diluting with hexanes and filtering the solution through a plug of celite to remove the catalyst. The solvents were evaporated and the residue was purified by column chromatography yielding the corresponding β-sulfanyl ketone. (silica gel chromatography, eluent 10-20% EtOAc in hexanes).
87% With iron(III) chloride In dichloromethane at 20℃;
  • 40
  • [ 3160-40-5 ]
  • [ 57791-63-6 ]
  • [ 1383844-32-3 ]
YieldReaction ConditionsOperation in experiment
67% With copper diacetate; trifluoroacetic acid In toluene at 140℃;
  • 41
  • [ 3160-40-5 ]
  • 4-hydroxydihydrocoumarin [ No CAS ]
  • (R)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With (S,S)-N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine; p-Toluic acid In toluene at 20℃; for 72h; enantioselective reaction;
  • 42
  • [ 104-88-1 ]
  • [ 67-64-1 ]
  • [ 3160-40-5 ]
  • 4-(4-chlorophenyl)-4-hydroxybutan-2-one [ No CAS ]
  • (S)-4-hydroxy-4-(4-chlorophenyl)butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 78 % ee 2: 7% With 1H-imidazole at 20℃; Flow reactor; Sonication; stereoselective reaction; General aspects of the preparation of aldol products in CF General procedure: For the CF method development, 20 mg (0.13 mmol, 1 eq) p-nitrobenzaldehyde (pNBA) and 0.9 mg (0.013 mmol, 0.1 eq) imidazole were dissolved in 5 mL acetone. The solution was homogenized by sonication for 3 min and was then pumped through the CF reactor under the appropriate conditions. The completion of the reaction was checked by TLC with a mixture of nhexane/ EtOAc as eluent. The crude aldol products were evaporated and then, if necessary, purified by column chromatography with a mixture of n-hexane/EtOAc as eluent. The b-hydroxyketones were characterized by NMR spectroscopy and chiral NP-HPLC. The detailed analytical data can be found in Supporting information. Between two reactions in the CF reactor, the catalyst bed was washed for 10 min with acetone at 1 mL min 1.
  • 43
  • [ 3160-40-5 ]
  • [ 622-79-7 ]
  • [ 1415129-36-0 ]
  • [ 1415129-38-2 ]
YieldReaction ConditionsOperation in experiment
1: 13% 2: 32% With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 72h; Cooling with ice; General synthetic procedure for enaminones 3-8: General procedure: to a solution of 1.0 mmol of enone 2a-f in 7 mL of CH2Cl2 under ice-bath cooling and magnetic stirring was added dropwise 0.25 mL (2 mmol) of BF3.Et2O and 2 mmol of benzyl azide. The reaction mixture was left for 15 min in the ice-bath and then it was removed and the stirring was continued at room temperature for the time indicated in each case. After this time, solid NaHCO3 was added until no more CO2 formation was noted. The organic phase was washed with water (20 mL), and the aqueous phase was extracted with CH2Cl2 (2 X 15 mL). The organic phases were reunited, washed with brine (15 mL), then dried over anhydrous MgSO4, filtered, and the solvent was evaporated. The crude residue was purified as indicated in each case.
  • 44
  • [ 3160-40-5 ]
  • [ 5164-76-1 ]
  • [ 1408280-69-2 ]
  • 45
  • [ 3160-40-5 ]
  • [ 71289-10-6 ]
  • 2,6-bis(4-chlorophenyl)-3'-methyl-1'-phenyl-1H-spiro[cyclohexane-1,4'-pyrazole]-4,5'(4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With benzoic acid; 9-amino-9-deoxy-epiquinine In toluene at 40℃; enantioselective reaction;
  • 46
  • [ 3160-40-5 ]
  • [ 626-35-7 ]
  • [ 1433962-93-6 ]
  • [ 1433962-80-1 ]
YieldReaction ConditionsOperation in experiment
1: 93 % ee 2: 93 % ee With ortho-nitrobenzoic acid; C21H31N3 In dichloromethane at 25℃; for 24h; Overall yield = 87 %; enantioselective reaction; General procedure for the catalytic Michael addition Reactions were performed with enone 3 (0.2 mmol) and 2 (44uL, 0.4 mmol, 2eq.) in the presence of catalyst 1f (0.02 mmol, 10 mol%) and acid additive 2-nitro benzoic acid (0.02 mmol, 10 mol%) in dichloromethane (0.5 mL) under aerobic atmosphere, taking no precaution to exclude moisture. After 24 to 40 h of stirring at room temperature (about 25 oC), the reaction mixture was quenched with 1mL 1 M aqueous HCl solution, extracted with EtOAc for three times. The combined organic layer was dried over Na2SO4, filtered, and concentrated to afford the corresponding Michael adduct 4 after purified by column chromatography on silica gel, eluting with petroleum ether and ethyl acetate
With benzoic acid In chloroform at 30℃; for 4h; Overall yield = 85 %; Optical yield = > 99 %ee; enantioselective reaction;
  • 47
  • [ 3160-40-5 ]
  • methyl 3-<2-<3-(5-methoxyindolyl)>ethylamino>acrylate [ No CAS ]
  • Methyl 9-methoxy-12b-methyl-2-(4-chlorophenyl)-1,2,6,7,12,12b-hexahydroindolo[2,3-a]-quinolizine-3-carboxylate [ No CAS ]
  • Methyl 9-methoxy-12b-methyl-2-(4-chlorophenyl)-1,2,6,7,12,12b-hexahydroindolo[2,3-a]-quinolizine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.667 % de With zinc(II) chloride In ethanol at 50℃; for 36h; diastereoselective reaction; General procedure for the preparations of 1,2,6,7,12,12bhexahydroindolo[2,3-a]quinolizines 4a-4g General procedure: A mixture of tryptamines (2.0 mmol) and methyl or ethyl propiolate (2.0 mmol) in 10.0 mL ethanol was stirred at room temperature for 20 min. Then arylideneacetones (2.0 mmol) and anhydrous zinc chloride (1.0 mmol, 0.136 g) were added to it. The solution was stirred at about 50 °C for additional 36 h. The solvent was removed by rotator evaporation and the residue was titrated with cold alcohol to give the pure product.
  • 48
  • [ 3160-40-5 ]
  • 3-(1-hydroxyethylidene)benzofuran-2(3H)-one [ No CAS ]
  • [ 1459161-05-7 ]
YieldReaction ConditionsOperation in experiment
82% With 3,5-dinitrobenzoic acid; (R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine In dichloromethane at 15℃; for 72h; Molecular sieve; stereoselective reaction; 5 4.3. Representative experimental procedure for asymmetric Michael-aldol-dehydration domino reaction General procedure: A mixture of 3-(1-hydroxyethylidene)benzofuran-2(3H)-one 2a (0.2 mmol), α,β-unsaturated ketone 3 (0.1mmol), 3,5-dinitrobenzoic acid (40 mol%), and catalyst 1b (20 mol%) was stirred in 0.5 mL dichloromethane at 15°C for 3 days (monitored by TLC). The reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/ethyl acetate) to furnish the corresponding products. 4.3.5. (1'S,6'R)-6'-(4-Chlorophenyl)-2'-methyl-2H-spiro[benzofuran-3,1'-cyclohex[2]ene]-2,4'-dione (4e). White solid, [α]D20 -105.7 (c 0.26, CHCl3), 82% yield; >20:1 dr, 93% ee, determined by HPLC (Chiralcel AD-H column, hexane/EtOH=92:8, 1.0 mL/min, 220 nm), tmajor=12.13 min, tminor=13.00 min. 1H NMR (300 MHz, CDCl3) δ 7.29-7.24 (m, 3H), 7.07-7.04 (m, 2H), 6.89-6.78 (m, 3H), 6.31 (s, 1H), 3.74-3.61 (m, 2H), 2.57 (dd, J=1.9 Hz, J=15 Hz, 1H), 1.66 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 196.9, 173.6, 154.4, 153.3, 134.8, 133.9, 130.7, 130.1, 129.4, 128.5, 128.0, 124.8, 123.7, 111.1, 58.7, 48.6, 38.1, 21.5; HRMS (EI) calcd for C20H15O3Cl [M]+: 338.0710; found: 338.0711.
  • 49
  • [ 3160-40-5 ]
  • [ 109-97-7 ]
  • (R)-4-(4-chlorophenyl)-4-(1H-pyrrol-2-yl)butan-2-one [ No CAS ]
  • (S)-4-(4-chlorophenyl)-4-(1H-pyrrol-2-yl)butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85 % ee With 9-amino-9-deoxy-epi-cinchonidine; trifluoroacetic acid In chlorobenzene at 0℃; for 72h; Overall yield = 85 %; Overall yield = 105 mg; enantioselective reaction; 2- Alklyated Pyrroles 3; General Procedure General procedure: Freshly distilled pyrrole (70 μL, 1.0 mmol) was added to a solutionof ketone (0.5 mmol), catalyst F (30 mg, 20 mol%), and TFA (14 μL, 30 mol%) in chlorobenzene (3.0 mL) at 0 °C for the stated time (Table 4). The crude reaction mixture was directly subjected to flash chromatography on silica gel.
  • 50
  • [ 3160-40-5 ]
  • C11H9BrO2 [ No CAS ]
  • C21H18BrClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With benzylamine; trifluoroacetic acid In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: C11H9BrO2 In tetrahydrofuran at 15℃; stereoselective reaction; General procedure for asymmetric Michael addition of 3(2H)-furanones 1 to α,β-unsaturatedketones 2 General procedure: A solution of α,β-unsaturated ketones 2 (0.24 mmol), catalyst 3d (0.02 mmol) and TFA (0.04 mmol) in THF (0.5 mL) was cooled to 0 °C and stirred for 10 minutes. Then, furanones 1(0.2 mmol) and THF(0.5 mL) were added, and the resulting mixture was stirred at 15 o C and monitored by TLC. The solvent was removed under vacuum and the residue was purified by flash chromatography on silica gel(petroleum ether/ethyl acetate = 5:1-3:1) to afford the corresponding addition product 4. All the products were confirmed by 1H NMR, 13C NMR and HRMS spectroscopic analysis. The diastereomeric ratio was determined by crude NMR analysis and the enantiomeric excess was determined by chiral-phase HPLC analysis.
  • 51
  • [ 3160-40-5 ]
  • C11H9BrO2 [ No CAS ]
  • C21H18BrClO3 [ No CAS ]
  • C21H18BrClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96 % ee Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With C19H23N3; trifluoroacetic acid In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: C11H9BrO2 In tetrahydrofuran at 15℃; Overall yield = 95 %; Overall yield = 82.3 mg; stereoselective reaction; General procedure for asymmetric Michael addition of 3(2H)-furanones 1 to α,β-unsaturatedketones 2 General procedure: A solution of α,β-unsaturated ketones 2 (0.24 mmol), catalyst 3d (0.02 mmol) and TFA (0.04 mmol) in THF (0.5 mL) was cooled to 0 °C and stirred for 10 minutes. Then, furanones 1(0.2 mmol) and THF(0.5 mL) were added, and the resulting mixture was stirred at 15 o C and monitored by TLC. The solvent was removed under vacuum and the residue was purified by flash chromatography on silica gel(petroleum ether/ethyl acetate = 5:1-3:1) to afford the corresponding addition product 4. All the products were confirmed by 1H NMR, 13C NMR and HRMS spectroscopic analysis. The diastereomeric ratio was determined by crude NMR analysis and the enantiomeric excess was determined by chiral-phase HPLC analysis.
  • 52
  • [ 3160-40-5 ]
  • [ 14400-67-0 ]
  • C16H17ClO3 [ No CAS ]
  • C16H17ClO3 [ No CAS ]
  • C16H17ClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A solution of alpha,beta-unsaturated ketones 2 (0.24 mmol), catalyst 3d (0.02 mmol) and TFA (0.04 mmol) in THF (0.5 mL) was cooled to 0 °C and stirred for 10 minutes. Then, furanones 1(0.2 mmol) and THF(0.5 mL) were added, and the resulting mixture was stirred at 15 o C and monitored by TLC. The solvent was removed under vacuum and the residue was purified by flash chromatography on silica gel(petroleum ether/ethyl acetate = 5:1-3:1) to afford the corresponding addition product 4. All the products were confirmed by 1H NMR, 13C NMR and HRMS spectroscopic analysis. The diastereomeric ratio was determined by crude NMR analysis and the enantiomeric excess was determined by chiral-phase HPLC analysis.
  • 53
  • [ 3160-40-5 ]
  • [ 14400-67-0 ]
  • C16H17ClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A solution of alpha,beta-unsaturated ketones 2 (0.24 mmol), catalyst 3d (0.02 mmol) and TFA (0.04 mmol) in THF (0.5 mL) was cooled to 0 °C and stirred for 10 minutes. Then, furanones 1(0.2 mmol) and THF(0.5 mL) were added, and the resulting mixture was stirred at 15 o C and monitored by TLC. The solvent was removed under vacuum and the residue was purified by flash chromatography on silica gel(petroleum ether/ethyl acetate = 5:1-3:1) to afford the corresponding addition product 4. All the products were confirmed by 1H NMR, 13C NMR and HRMS spectroscopic analysis. The diastereomeric ratio was determined by crude NMR analysis and the enantiomeric excess was determined by chiral-phase HPLC analysis.
  • 54
  • [ 3160-40-5 ]
  • [ 71730-46-6 ]
  • (8R,11aR)-8-(4-chlorophenyl)-11,11a-dihydro-8H-benzo[e]pyrido[1,2-c][1,2,3]oxathiazin-10(9H)-one 6,6-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With (1R)-(6-methoxyquinolin-4-yl)((2R)-5-vinylquinuclidin-2-yl)methanamine; o-fluoro-benzoic acid In toluene at 20℃; Inert atmosphere; enantioselective reaction;
  • 55
  • [ 3160-40-5 ]
  • C27H32N3OP [ No CAS ]
  • C37H41ClN3O2P [ No CAS ]
  • C37H41ClN3O2P [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 % de Stage #1: 4-(4-chlorophenyl)-3-buten-2-one With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: C27H32N3OP In tetrahydrofuran at -78℃; for 30h; Inert atmosphere; Cooling with acetone-dry ice; Overall yield = 74 %; diastereoselective reaction; 3.General procedure for addition reaction of imines General procedure: Into a reaction vialunder argon, enones 2 (0.4 mmol) was taken followed by THF (4.0 mL) at -78 oCusing dry ice-acetone bath, then LiHMDS (0.3 mmol) was added, and the mixturewas kept in this temperature for 45 min. At the same time, imine 1 (0.15 mmol, dissolved in 3.0 mL ofTHF) properly sealed with a rubber septum in dry argon atmosphere, was cooledto -78 oC in the same dry ice-acetone bath for 5 min. Then the imine wasadded dropwise via a cannula at -78 oCand stirring was continued for 30 h at the same temperature. After confirmingthe consumption of imine, the reaction mixture was quenched with saturated ammoniumchloride (4.0 mL) and the organic layer was extracted with ethyl acetate. Theorganic layers were dried over anhydrous Na2SO4, filteredand concentrated under reduced pressure. The crude product was purified usingflash column chromatography on silica gel using EtOAc/Hexanes (1:10 to 2:1,v/v) as the eluent to afford adduct 3.
  • 56
  • [ 3160-40-5 ]
  • [ 108-88-3 ]
  • α-Benzyl-p-chlorstyryl-methyl-keton [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With di-tert-butyl peroxide; [copper(II)(trifluoroacetylacetonate)2]; salicylic acid at 120℃; for 24h; Inert atmosphere; regioselective reaction;
  • 57
  • [ 3160-40-5 ]
  • [ 14150-94-8 ]
  • 2-[2-(4-chlorophenyl)ethenyl]-5-nitropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With ammonium acetate; In ethanol; at 80℃; for 4h;Microwave irradiation; General procedure: To a solution of the dinitropyridone 1 (50 mg, 0.25 mmol) in ethanol (10 mL), 4-phenyl-3-buten-2-one (4a) (36.5 mg, 0.25 mmol) and NH4OAc (578 mg, 7.5 mmol) were added, and the resultant mixture was heated at 65 C for 24 h. After removal of the solvent, the residue was washed with benzene (3 × 10 mL) to remove unreacted ketone 4a and treated with column chromatography on silica gel (eluent: hexane/ethyl acetate =95/5) to afford 5-nitro-2-(2-phenylethenyl)pyridine (5a) (41 mg, 0.18 mmol, 72%) as a yellow powder. The reactions of the dinitropyridone 1 with other ketones 4b-f or 10a-c were performed in a similar way.
  • 58
  • [ 3160-40-5 ]
  • [ 171-74-4 ]
  • C23H24ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With (2S)-2-([(1R,2R)-2-aminocyclohexyl]carbamothioyl}amino)-N-benzyl-N,3,3-trimethylbutanamide; benzoic acid In 5,5-dimethyl-1,3-cyclohexadiene at 30℃; for 72h; stereoselective reaction;
  • 59
  • [ 3160-40-5 ]
  • C13H14BrN [ No CAS ]
  • C23H23BrClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With (2S)-2-([(1R,2R)-2-aminocyclohexyl]carbamothioyl}amino)-N-benzyl-N,3,3-trimethylbutanamide; benzoic acid In 5,5-dimethyl-1,3-cyclohexadiene at 40℃; for 48h; stereoselective reaction;
  • 60
  • [ 3160-40-5 ]
  • [ 2436-21-7 ]
  • C23H26ClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With (2S)-2-([(1R,2R)-2-aminocyclohexyl]carbamothioyl}amino)-N-benzyl-N,3,3-trimethylbutanamide; benzoic acid In 5,5-dimethyl-1,3-cyclohexadiene at 40℃; for 72h; stereoselective reaction;
  • 61
  • [ 3160-40-5 ]
  • [ 95-14-7 ]
  • 4-(1H-benzo[d][1,2,3]triazol-1-yl)-4-(4-chlorophenyl)butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With diethylamine In toluene at 40 - 60℃; for 48h; Generalprocedure for the synthesis of the β-benzotriazolyl carbonyl compounds 1 and 31 General procedure: A mixture of unsaturatedketones2 (10 mmol), benzotriazole (12 mmol), diethyl amine(5 mmol), toluene (30 ml) was stirred at 40-60 for 48 hours. The mixture wasextracted with ethyl acetate (3 30ml). The organic phase was dried over anhydroussodium, and concentrated under reduced pressure. The residue was purified bychromatography on silica gel (300-400 mesh) using petroleum/EtOAc (5/1, v : v)as the eluent to afford the corresponding substrates 1 and 3. Compounds 1a, 1b, 1g, 1h, 1j, 1k and 3a are known compounds.1 Compounds1c, 1d, 1e, 1f, 1i, 1l, 1m, 1n, 3b-3j are new compounds that wereprepared using the same method. The overall yields of their Bt-1 and Bt-2isomers were given since either of the isomers could be used as the substratesin the following reductive coupling cyclization reaction
  • 62
  • [ 3160-40-5 ]
  • [ 99893-14-8 ]
  • (R)-1-acetyl-3-((S)-1-(4-chlorophenyl)-3-oxobutyl)-3-methylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With L-Tartaric acid; (R)-1-methoxy-1, 1-diphenyl-3-(piperidin-1-yl) propan-2-amine In toluene at 0℃; for 72h; stereoselective reaction;
  • 63
  • [ 3160-40-5 ]
  • [ 1504-06-9 ]
  • C19H18ClNO2 [ No CAS ]
  • (R)-3-((R)-1-(4-chlorophenyl)-3-oxobutyl)-3-methylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With Boc-D-Phg-OH; (R,R)-1,2-diphenylethylenediamine In toluene at 20℃; for 24h; stereoselective reaction;
  • 64
  • [ 3160-40-5 ]
  • [ 622-79-7 ]
  • C17H14ClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With zinc(II) oxide In water at 80℃; for 5h; Green chemistry; regioselective reaction; b) Procedure for the triazole synthesis: General procedure: To a mixture of β-nitrostyrene/ chalcone (1 eqv) in water (4 mL) were added azide (1.5 eqv), Zn(OAc)2 (20 mol%) and t BuOOH (1 eqv)/ZnO nanoparticle (10 mol %) at room temperature and the mixture was heated at 80-90 °C for 3-5 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature and extracted with EtOAc (3 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate to give the crude product. Purification of the crude product using petroleum ether-EtOAc gave the desired product (please see the Electronic Supporting Information for spectral data).
90% With copper(ll) sulfate pentahydrate; bismuth tungstate; sodium L-ascorbate In toluene at 80℃; for 6h; regioselective reaction;
  • 65
  • [ 3160-40-5 ]
  • [ 104-88-1 ]
  • [ 18278-29-0 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In ethanol; water at 25 - 30℃; Enones 2a - h (general procedure). General procedure: A solution of sodium hydroxide (1 g, 0.025 mol) in water (10 mL) was added dropwise to a mixture of aldehyde (0.2 mol), the corresponding methyl ketone (0.2 mol) or acetone (0.1 mol), and ethanol (100 mL) at 25-30° C. The mixture was allowed to stand for 2 h under the specified conditions and then cooled to 0 °C. The precipitate that formed was filtered, washed with water, dried, and recrystallized from the appropriate solvent.
  • 66
  • [ 3160-40-5 ]
  • [ 1392239-32-5 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrile at 20℃;
With phenyltrimethylammonium tribromide In tetrahydrofuran at 25℃; 4.3. Procedure for the preparation of anthranilates 3aej General procedure: Benzylidenacetone 1aej (0.05 mol) was dissolved in tetrahydrofuran(30 mL). Phenyl trimethyl ammonium tribromide(0.05 mol, 11.3 g) was charged into the solution at 25 °C. After starting materials were consumed (45 min), the reaction mixture was poured into ice-cold water (300 mL). The product was extracted with diethylether (3 50 mL), and the combined organic layers were washed with water, brine and dried over Na2SO4 and evaporated under reduced pressure at room temperature. The residue was dissolved in DMF (5 mL) and added drop wise over 5 min to a solution of anthranilic acid (0.05 mol; 6.9 g) and triethylamine (0.05 mol; 7 mL) in DMF (50 mL). After starting materials were consumed (TLC monitoring), the reaction mixture was poured into water with crushed ice (500 mL), the resulting suspension was filtered and the cake was thoroughly washed withwater and dried. Crude anthranilate was purified by the crystallizationprocess.
  • 67
  • [ 3160-40-5 ]
  • [ 4827-64-9 ]
  • C18H16ClNO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With (S)-N<SUP>1</SUP>-cyclohexyl-3,3-dimethylbutane-1,2-diamine; benzoic acid In ethyl acetate at 20℃; for 48h; stereoselective reaction;
  • 68
  • [ 3160-40-5 ]
  • 3,4-difluoro-4-(4-chlorophenyl)-2-butanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With fluorine In ethanol; chloroform; trichlorofluoromethane at -78℃; Inert atmosphere; 4.1 General fluorination procedure General procedure: Caution: fluorine is a strong oxidant and corrosive material. In organic chemistry, it is used after dilution with nitrogen or helium (generally from 1 to 20% depending on the reaction type). It should be remembered that dilute fluorine is less dangerous and easier to work with than chlorine (it is also less toxic than Cl2 ()25). The reactions should be performed in a well-ventilated area. Prediluted fluorine (10% in N2) is commercially available. If preferred, however, technical (>95%) F2 could be used and diluted on the spot to whatever degree desired by using a simple vacuum line requiring only a simple soda-lime trap at their outlet. A detailed description for a simple setup had appeared in the past.26 The reactions themselves are carried out in regular glassware. If elementary precautions are taken, work with F2 is simple and we have had no bad experience working with it. (0015) The reactions were usually carried out on scales of 2-7mmol of α,β-unsaturated carbonyl compounds, monitored by TLC, GC or NMR. Fluorine, at concentrations of 7-10% in N2, was slowly passed through a cold (-78°C) and vigorously stirred solution of the enone dissolved in 100mL of CFCl3 (could be replaced by dry acetonitrile or HFC-134 with somewhat lower yields), 125mL CHCl3 and 5-25mL of EtOH. An efficient mixing is achieved by using a vibromixer, which also ensures a fine dispersion of the gas bubbles. In most cases the reactions were completed within 2-4h. They were terminated by pouring into 200mL water, washing the organic layer with NaHCO3 solution followed by water till neutral, drying over MgSO4, and finally evaporating the solvent. The crude product was usually purified by vacuum flash chromatography using silica gel 60-H (Merck) followed by recrystallization if needed.
  • 69
  • [ 3160-40-5 ]
  • [ 186534-02-1 ]
  • (1E,4E)-1-(4-chlorophenyl)-5-(3,5,6-trimethylpyrazin-2-yl)penta-1,4-dien-3-one [ No CAS ]
  • 70
  • [ 3160-40-5 ]
  • [ 557-20-0 ]
  • 4-(4-chlorophenyl)-2-hexanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With (R)-(2-(tert-butylsulfinyl)-6-methoxyphenyl)diphenylphosphine; copper(II) bis(trifluoromethanesulfonate) In hexane; dichloromethane at -30℃; for 24h; Inert atmosphere; enantioselective reaction; 10 General procedure for copper-catalyzed asymmetric conjugate addition General procedure: A mixture of Cu(OTf)2 (3.6 mg, 0.01 mmol) and L2 (4.8 mg, 0.012 mmol) in DCM or DCE (2 mL) was stirred at room temperature for 1 h under argon. The mixture was cooled to -30 °C and diethylzinc (1.1 mmol, 1.1 mL of 1.0 M solution in hexane) wad added dropwise. After stirring for 5 min at -30 °C the enone (1.0 mmol) in 1 mL solvent was added. The reaction was lasted at -30 °C for 24 h then quenched with saturated NH4Cl aqueous solution. The mixture was extracted with diethyl ether. The combined organic layers were washed with NaHCO3 and brine then dried over Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography. The enantiomeric excess of the product was determined by chiral HPLC.
  • 71
  • [ 3160-40-5 ]
  • [ 75-52-5 ]
  • [ 1092103-59-7 ]
YieldReaction ConditionsOperation in experiment
96% With 9-epi-9-amino-9-deoxyquinine; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; benzoic acid at 40℃; for 48h; enantioselective reaction; 2. General procedure for the asymmetric Michael reaction: General procedure: 9-amino-epi-quinine 4 (6.5 mg, 0.04 mmol), α,β-unsaturated enones (0.2 mmol) and benzoic acid (9.9 mg, 0.08 mmol) were stirred in redistilled nitromethane at 40 °C. After due reaction time, the reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography onsilica gel (EtOAc/petroleum ether) to afford the desired Michael adduct. The enantiomeric excess was determined by HPLC analysis on chiral column.
84% With C59H86N10O9; benzoic acid In tetrahydrofuran at 40℃; for 72h; Sealed tube; enantioselective reaction;
  • 72
  • [ 3160-40-5 ]
  • [ 925-90-6 ]
  • [ 28995-88-2 ]
  • (1E,4Z)-1-(4-chlorophenyl)-3-methyl-5-phenyl-4-tosylhepta-1,4-dien-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: ethylmagnesium bromide; 1-methyl-4-((phenylethynyl)sulfonyl)benzene With copper(l) cyanide In diethyl ether; dichloromethane at 0℃; Schlenk technique; Inert atmosphere; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one In diethyl ether; dichloromethane at 0℃; for 4h; Schlenk technique; Inert atmosphere; General experimental procedure for the synthesis of diallylic alcohols 4 General procedure: A Schlenk flask was charged with 0.5mmol (128mg) of 1-phenyl-2-(p-tosyl)ethyne (1a), 0.6mmol of ethylmagnesium bromide (2a), 0.05mmol (4.5mg) of CuCN and 5mL of Et2O/CH2Cl2 (v/v 2/3) under argon atmosphere. The reaction mixture was stirred at 0°C. After the full consumption of 1a (monitored by TLC), 0.6mmol (146mg) of (E)-3-(p-chlorophenyl)-1-phenylpropenone (3a) was added and the reaction mixture was stirred for 4hat 0°C. The reaction was then quenched with saturated NH4Cl and extracted with ethyl acetate (3×10mL). The organic layer was dried over anhydrous Na2SO4. After filtration and removal of the solvent in vacuo, the crude product was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1/15) to give the product 4a.
  • 73
  • [ 3160-40-5 ]
  • [ 1589-82-8 ]
  • [ 28995-88-2 ]
  • (1E,4Z)-1-(4-chlorophenyl)-3-methyl-5,6-diphenyl-4-tosylhexa-1,4-dien-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: phenylmagnesium bromide; 1-methyl-4-((phenylethynyl)sulfonyl)benzene With copper(l) cyanide In diethyl ether; dichloromethane at 0℃; Schlenk technique; Inert atmosphere; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one In diethyl ether; dichloromethane at 0℃; for 4h; Schlenk technique; Inert atmosphere; General experimental procedure for the synthesis of diallylic alcohols 4 General procedure: A Schlenk flask was charged with 0.5mmol (128mg) of 1-phenyl-2-(p-tosyl)ethyne (1a), 0.6mmol of ethylmagnesium bromide (2a), 0.05mmol (4.5mg) of CuCN and 5mL of Et2O/CH2Cl2 (v/v 2/3) under argon atmosphere. The reaction mixture was stirred at 0°C. After the full consumption of 1a (monitored by TLC), 0.6mmol (146mg) of (E)-3-(p-chlorophenyl)-1-phenylpropenone (3a) was added and the reaction mixture was stirred for 4hat 0°C. The reaction was then quenched with saturated NH4Cl and extracted with ethyl acetate (3×10mL). The organic layer was dried over anhydrous Na2SO4. After filtration and removal of the solvent in vacuo, the crude product was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1/15) to give the product 4a.
  • 74
  • [ 693-03-8 ]
  • [ 3160-40-5 ]
  • [ 28995-88-2 ]
  • (1E,4Z)-1-(4-chlorophenyl)-3-methyl-5-phenyl-4-tosylnona-1,4-dien-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: n-butyl magnesium bromide; 1-methyl-4-((phenylethynyl)sulfonyl)benzene With copper(l) cyanide In diethyl ether; dichloromethane at 0℃; Schlenk technique; Inert atmosphere; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one In diethyl ether; dichloromethane at 0℃; for 4h; Schlenk technique; Inert atmosphere; General experimental procedure for the synthesis of diallylic alcohols 4 General procedure: A Schlenk flask was charged with 0.5mmol (128mg) of 1-phenyl-2-(p-tosyl)ethyne (1a), 0.6mmol of ethylmagnesium bromide (2a), 0.05mmol (4.5mg) of CuCN and 5mL of Et2O/CH2Cl2 (v/v 2/3) under argon atmosphere. The reaction mixture was stirred at 0°C. After the full consumption of 1a (monitored by TLC), 0.6mmol (146mg) of (E)-3-(p-chlorophenyl)-1-phenylpropenone (3a) was added and the reaction mixture was stirred for 4hat 0°C. The reaction was then quenched with saturated NH4Cl and extracted with ethyl acetate (3×10mL). The organic layer was dried over anhydrous Na2SO4. After filtration and removal of the solvent in vacuo, the crude product was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1/15) to give the product 4a.
  • 75
  • [ 3160-40-5 ]
  • [ 28995-88-2 ]
  • [ 1730-25-2 ]
  • (1E,4Z)-1-(4-chlorophenyl)-3-methyl-5-phenyl-4-tosylocta-1,4,7-trien-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 1-methyl-4-((phenylethynyl)sulfonyl)benzene; allylmagnesium bromide With copper(l) cyanide In diethyl ether; dichloromethane at 0℃; Schlenk technique; Inert atmosphere; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one In diethyl ether; dichloromethane at 0℃; for 4h; Schlenk technique; Inert atmosphere; General experimental procedure for the synthesis of diallylic alcohols 4 General procedure: A Schlenk flask was charged with 0.5mmol (128mg) of 1-phenyl-2-(p-tosyl)ethyne (1a), 0.6mmol of ethylmagnesium bromide (2a), 0.05mmol (4.5mg) of CuCN and 5mL of Et2O/CH2Cl2 (v/v 2/3) under argon atmosphere. The reaction mixture was stirred at 0°C. After the full consumption of 1a (monitored by TLC), 0.6mmol (146mg) of (E)-3-(p-chlorophenyl)-1-phenylpropenone (3a) was added and the reaction mixture was stirred for 4hat 0°C. The reaction was then quenched with saturated NH4Cl and extracted with ethyl acetate (3×10mL). The organic layer was dried over anhydrous Na2SO4. After filtration and removal of the solvent in vacuo, the crude product was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1/15) to give the product 4a.
  • 76
  • [ 3160-40-5 ]
  • 2,2,2-trifluoroethyl 2-[(1,3-dithian)-2-yl]-ethanthioate [ No CAS ]
  • C17H18ClF3O2S3 [ No CAS ]
  • C17H18ClF3O2S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With salicylic acid; (8R,9R)-9-amino(9-deoxy)epicinchonin In toluene at 25 - 40℃; for 2h; Microwave irradiation; Overall yield = 47 %; Optical yield = 32 %ee; enantioselective reaction; General Procedure for the Microwave-Assisted Reactions General procedure: The catalyst, the co-catalytic acid and the dithianilthioester(0.15 mmol) were dissolved in dry toluene; the α,β-unsaturatedketone was then added at 25 °C. The stirred reaction mixturewas then heated at 40 °C under constant microwave irradiation(MW power was set to 200 W) for the desired time. After thisperiod, the solvent was removed under reduced pressure, andthe crude was purified by flash column chromatography.
  • 77
  • [ 3160-40-5 ]
  • [ 5439-39-4 ]
  • C22H17ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyrrolidine; benzoic acid In toluene at 50℃; for 48h; 4.3. General procedure a for the preparation of rac-substituted cyclohexanones General procedure: All reactions were carried out in normal toluene and no special precautions were taken to exclude water or air from the reaction flask. Pyrrolidine (0.1 mmol) and benzoic acid (6.0 mg, 0.05 mmol) were added to a stirred solution of the allylidene malononitriles 2(0.2 mmol) and enones 1 (0.4 mmol) in toluene (1 mL). Then the reaction mixture was stirred at 50 C for 2 d. Next, the solvent was removed under reduced pressure and the resulting residue was directly subjected to column chromatography on silica gel to afford the corresponding products rac-3a-3d
  • 78
  • [ 3160-40-5 ]
  • [ 5439-39-4 ]
  • (2S,6S)-4-oxo-2-(4-chlorophenyl)-6-styrylcyclohexane-1,1-dicarbonitrile [ No CAS ]
  • C22H17ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With 9-amino-9-deoxy-epihydroquinine; benzoic acid In water at 28℃; for 72h; Green chemistry; enantioselective reaction; 4.5. General procedure C for the preparation of chiral cyclohexanone derivatives General procedure: All the reactions were carried out in double distilled water and no special precautions were taken to exclude air from the reaction flask. Benzoic acid (7.5 mg, 0.06 mmol) was added to a heterogeneous mixture of the catalyst V (13 mg, 0.04 mmol) and water(0.5 mL). The resulting heterogeneous mixture was stirred at40 C for 10 min in a pre-heated oil bath. Next, the mixture was brought to room temperature and enone 1 (0.4 mmol, 2 equiv)was added, followed by the addition of allylidene malononitrile 2(0.2 mmol, 1 equiv) or allylidene cyanoacetate 4. The heterogeneous mixture was stirred at 28 C for 3 d. The reaction mixture was extracted with dichloromethane (3 10 mL) and the combined extract was washed with brine, dried (MgSO4) and evaporated.The residue was purified by column chromatography on silica using hexane/EtOAc as eluent to give 3a-3m and 5a-5c.
  • 79
  • [ 3160-40-5 ]
  • [ 6295-87-0 ]
  • 1-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With oxygen In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Phenyl(2-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone (3a);Typical Procedure General procedure: A clean, washed boiling tube equipped with a magnetic stir bar was charged with 1-aminopyridinium iodide (1a) (0.0665 g, 0.3 mmol),(E)-chalcone (2a) (0.0520 g, 0.25 mmol) and NMP (1 mL). The mixture was stirred for 24 h at r.t. under O2 (balloon). After completion of the reaction, the mixture was poured into hypo solution (10 mL). The mixture was extracted with EtOAc (3 × 10 mL), dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. The residue was purified through column chromatography using silica gel (20%EtOAc/hexane) to afford 3a.
  • 80
  • [ 3160-40-5 ]
  • [ 1750-12-5 ]
  • 9-amino-5-(4-chlorophenyl)-3-methyl-4,9-dihydro-5H-[1,2,4]triazolo[5,1-c][1,2,4]triazepine-8-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide In ethanol; water for 8h; Heating; regioselective reaction; Synthesis of 9-amino-5-(4-chlorophenyl)-3-methyl-4,9-dihydro-5H-[1,2,4]-triazolo [5,1-c][1,2,4]triazepine-8-thiol (11) An equimolar amount (0.01 mol) of 4-(4-chlorophenyl)but-3-en-2-one and 4-amino-5- hydrazino-4H-[1,2,4]triazol-3-thiol was heated in 60 ml alcoholic sodium hydroxide 0.5M (1.2 g NaOH in 40 ml ethanol and 20 ml water) for 8 h (monitored with TLC). After completion of reaction, the reaction mixture was cooled to RT, poured into ice-cold distilled water, and neutralized to pH ∼6.5 with dilute hydrochloric acid. The formed crude precipitate was collected by filtration, washed several times with distilled water, and dried. For elemental analyses the crude was recrystallized from ethanol to give 11. Yield 81%; white solid; mp: 252-253 °C. IR (ATR) νmax 3328, 3230, 3060, 2987, 2948, 2874, 1636 cm1. 1H NMR (400 MHz, DMSO-d6) δ 12.17 (s, 1H, SH), 7.39 (s, 4H, CHarom), 5.59 (s, 2H, NH2), 5.31 (t, j 10.6 Hz, 1H, CHtriazepine), 3.40 (dd, j 17.4, 11.0 Hz, 1H, CH2), 2.81 (dd, j 17.4, 10.4 Hz, 1H, CH2), 2.03 (s, 3H, CH3). 13C NMR (100 MHz, DMSO-d6) δ 164.6, 156.5, 149.8, 139.8, 132.6, 129.1, 128.9, 64.0, 46.3, 15.8. Anal. Calcd. for C12H13ClN6S (308): C, 46.68; H, 4.24; N, 27.22. Found: C, 46.71; H, 4.21; N, 27.32.
  • 81
  • [ 3160-40-5 ]
  • [ 1774-47-6 ]
  • [ 54064-34-5 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: trimethylsulfoxonium iodide With potassium <i>tert</i>-butylate In dimethyl sulfoxide for 0.5h; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one In dimethyl sulfoxide for 3h;
  • 82
  • [ 3160-40-5 ]
  • [ 126-81-8 ]
  • C18H21ClO3 [ No CAS ]
  • 4-(4-chlorophenyl)-2-hydroxy-2,7,7-trimethyl-2,3,4,6,7,8-hexahydro-5H-chromen-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
97 % ee With 9-epi-9-amino-9-deoxyquinine; salicylic acid In tetrahydrofuran at 0℃; for 96h; Overall yield = 99 %; enantioselective reaction; 3.2. General Procedure for the Asymmetric Michael Reaction of Cinnamones General procedure: 9-Amino-epi-quinine 3a (6.5 mg, 0.02 mmol), α,β-unsaturated enones (0.12 mmol), dimedone(14.0 mg, 0.1 mmol), and salicylic acid (4.9 mg, 0.04 mmol) were dissolved in THF (1 mL) withoutstirring. Once the solution was cooled down to 0 °C, the reaction mixture was stirred for 96 h.After the solvent was removed in vacuo, the residue was purified by flash chromatography on silicagel (EtOAc/petroleum ether) to afford the desired 3,4-dihydropyran.
  • 83
  • [ 3160-40-5 ]
  • [ 504-02-9 ]
  • 4-(4-chlorophenyl)-2-hydroxy-2-methyl-2,3,4,6,7,8-hexahydro-5H-chromen-5-one [ No CAS ]
  • C16H17ClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95 % ee With 9-epi-9-amino-9-deoxyquinine; salicylic acid In tetrahydrofuran at 0℃; for 96h; Overall yield = 78 %; enantioselective reaction; 3.2. General Procedure for the Asymmetric Michael Reaction of Cinnamones General procedure: 9-Amino-epi-quinine 3a (6.5 mg, 0.02 mmol), α,β-unsaturated enones (0.12 mmol), dimedone(14.0 mg, 0.1 mmol), and salicylic acid (4.9 mg, 0.04 mmol) were dissolved in THF (1 mL) withoutstirring. Once the solution was cooled down to 0 °C, the reaction mixture was stirred for 96 h.After the solvent was removed in vacuo, the residue was purified by flash chromatography on silicagel (EtOAc/petroleum ether) to afford the desired 3,4-dihydropyran.
  • 84
  • [ 3240-35-5 ]
  • [ 3160-40-5 ]
  • 4-((1E,4E)-5-(4-chlorophenyl)-3-oxopenta-1,4-dien-1-yl)benzenesulfonamide [ No CAS ]
  • 85
  • [ 534-22-5 ]
  • [ 3160-40-5 ]
  • 4-(4-chlorophenyl)-4-(5-methylfuran-2-yl)butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With copper(ll) bromide In dichloromethane at 20℃; for 4h; Preparation of compounds 3q-u (General method). General procedure: CuBr2 (2.8 mg, 2.5 mol %) was added to a solution of ketone 2 (0.5 mmol) and furan 1 (0.5 mmol) in dichloromethane (1.25 ml). The reaction mixture was stirred for 4 h at room temperature while controlling the reaction progress by TLC. Upon comletion, the mixture was concentrated at reduced pressure. The product was isolated by column chromatography (eluent petroleum ether - CH2Cl2, gradient from 19:1 to 1:1).
  • 86
  • [ 3160-40-5 ]
  • [ 100-63-0 ]
  • [ 87623-79-8 ]
YieldReaction ConditionsOperation in experiment
90% With bis(triphenylphosphane)copper(I) nitrate; potassium hydroxide In ethanol at 20℃; for 0.0166667h; Sonication; Synthesis of 1,5-diaryl pyrazolines and 1,3,5-triaryl-2-pyrazolines General procedure: The chalcones were prepared from acetone or acetophenone and aromatic aldehydes by reported method. Pyrazoline derivatives were prepared by dissolving chalcones (10 mmol) and phenyl hydrazine (10 mmol) in alcoholic KOH (1 g KOH in 40 mL ethanol) in a 100 mL conical flask. Then Cu(PPh3)2NO3 catalyst (10 mol % i.e. 62 mg) was added in the reaction mixture. The mixture was irradiated in the water bath of an ultrasonic cleaner for the period shown in Table-2. After completion of the reaction, the reaction mixture was poured in ice water and filtered. The crude products were recrystallized in ethanol to obtained the 1,5-driaryl pyrazolines and 1,3,5-triaryl-2-pyrazolines. The compounds were analyzed by FTIR and 1H NMR spectroscopy.
  • 87
  • [ 3160-40-5 ]
  • [ 120-12-7 ]
  • C24H19ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; diastereoselective reaction;
  • 88
  • [ 505-23-7 ]
  • [ 3160-40-5 ]
  • 3-((1-(4-chlorophenyl)-3-oxobutyl)thio)propyl methanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 1,3 dithiane With N-chloro-succinimide In dichloromethane at 0℃; Stage #2: 4-(4-chlorophenyl)-3-buten-2-one With iron(III) chloride hexahydrate In dichloromethane at 20℃;
83% With N-chloro-succinimide; iron(III) chloride hexahydrate In dichloromethane at 20℃; for 8h; 3 In a 10 ml round bottom flask,Add 1,3-dithiane 2 (30 mg, 0.25 mmol),After dissolving in 2 ml of dichloromethane, N-chlorosuccinimide (40 mg, 0.3 mmol) was added.Add FeCl3.6H2O (7mg, 0.025mmol),1c (38 mg, 0.21 mmol) was stirred in air and stirred at room temperature for 8 h.The TLC was stopped after the reaction was completed, and the solvent was distilled off, followed by column chromatography to obtain the product 3c.The obtained product data was characterized as follows: yellow oil; yield 83%;
  • 89
  • [ 3160-40-5 ]
  • [ 106-42-3 ]
  • C18H19ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With copper(II) bis(trifluoromethanesulfonate); 9-(2-mesityl)-10-methylacridinium perchlorate In 1,2-dichloro-ethane at 20℃; Irradiation;
  • 90
  • [ 3160-40-5 ]
  • [ 126-81-8 ]
  • 4-(4-chlorophenyl)-2-hydroxy-2,7,7-trimethyl-2,3,4,6,7,8-hexahydro-5H-chromen-5-one [ No CAS ]
  • C18H21ClO3 [ No CAS ]
  • C18H21ClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
8 % ee With streptomyces griseus protease In tetrahydrofuran; water at 30℃; for 96h; Enzymatic reaction; Overall yield = 66 %; enantioselective reaction; 4.2 General Procedure for the SGP-Catalyzed Synthesis of 3,4-Dihydropyran Derivatives General procedure: A mixture of ,-unsaturated ketone or ester 1 (0.54mmol),dimedone 2 (0.30mmol), SGP (203 U), THF (0.675mL)and deionized water (0.075mL) was stirred for the specifiedtime at 30°C, and monitored by TLC analysis. Aftercompletion, the enzyme was fltered out; ethyl acetate wasused to wash the residue on the filter paper. The filtrate wasconcentrated under vacuum. The residue was purified byflash column chromatography on silica gel using a mixtureof petroleum ether and ethyl acetate (petroleum ether/ethylacetate = 3/1-8/1, v/v) as eluent to give the products.
  • 91
  • [ 3160-40-5 ]
  • [ 4712-55-4 ]
  • diphenyl (S,E)-(4-(4-chlorophenyl)-2-hydroxybut-3-en-2-yl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With C39H50N6O In toluene at -60℃; for 70h; Molecular sieve; enantioselective reaction;
  • 92
  • [ 3160-40-5 ]
  • [ 4139-61-1 ]
  • (4R)-9-bromo-4-(4-chlorophenyl)-2-hydroxy-2-methyl-3,4-dihydropyrano[3,2-c]chromene-5(2H)-one [ No CAS ]
  • 93
  • [ 3160-40-5 ]
  • [ 4139-61-1 ]
  • C19H14BrClO4 [ No CAS ]
  • 94
  • [ 3160-40-5 ]
  • [ 94-02-0 ]
  • C21H21ClO4 [ No CAS ]
  • C21H21ClO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C54H39F6N3OPS(1+)*F6P(1-) In ethanol at 25℃; for 72h; 4.3 Example 4 Compound 5 (0.5 mmol) was added sequentially to a reaction tube with a ground glass stopper.Compound 6 (1.0 mmol), Catalyst 1 (0.05 mmol) and ethanol (2 mL),The reaction was carried out at 25 ° C for 72 to 120 h. Filter and wash with ice ethanol (1 mL×3).Drying in vacuo gave Compound 7. The filtrate was distilled under reduced pressure to remove the solvent.Dissolved in a small amount of dichloromethane (1 mL), EtOAc (EtOAc)The results of the catalytic reaction are shown in Table 1.
  • 95
  • [ 3160-40-5 ]
  • [ 108-59-8 ]
  • dimethyl (R)-2-[1-(4-chlorophenyl)-3-oxobutyl]malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With C59H86N10O9; benzoic acid In tetrahydrofuran at 40℃; for 96h; enantioselective reaction; General procedure A General procedure: A mixture of α,β-unsaturated ketone 6 (0.200 mmol), dimethyl malonate (68.5 μL, 0.600 mmol), peptide 1 (43.2 mg, 0.0400 mmol), and benzoic acid (4.9 mg, 0.040 mmol) in THF (0.5 mL) was heated at 40 °C for four days. The reaction mixture was diluted with 50% EtOAc in n-hexane and was passed through a short plug of silica gel eluted with 50% EtOAc in n-hexane. After removal of solvent, the residue was purified by flash column chromatography on silica gel (eluent: EtOAc in n-hexane) to give the desired adduct 7. The absolute stereochemistry was determined by comparison with literature compounds on the basis of specific rotation and HPLC chromatogram.
  • 96
  • [ 118-90-1 ]
  • [ 3160-40-5 ]
  • C16H13ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With indium(III) triflate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium carbonate In tert-Amyl alcohol; water at 140℃; for 16h;
  • 97
  • [ 118-90-1 ]
  • [ 3160-40-5 ]
  • C18H15ClO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium acetate In water at 150℃; for 16h;
  • 98
  • [ 3160-40-5 ]
  • [ 32271-56-0 ]
  • (S)-4-(4-chlorophenyl)but-3-en-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.6 % ee With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; tris(o-methoxyphenyl)phosphine; hydrogen; sodium hydroxide; (8R,9R)-9-amino(9-deoxy)epicinchonin In ethanol at 30℃; for 2h; Autoclave; enantioselective reaction; General experimental procedure General procedure: All reagents were of analytical grade and used as-received withoutfurther purification. The purity of hydrogen was over 99.99%.1HNMR spectra were recorded on JEOL NMR 400 MHz spectrometerwith reference to TMS as the internal standard. Product weredetermined by GC-9790 with a b-DEX120 column(25 m 0.25 mm) and LC-16 with Chirasil OB-H column(25 cm 4.6 mm), Chirasil IA column (25 cm 4.6 mm) and ChirasilIB column (25 cm 4.6 mm). Iridium precursor, chiral diamine,achiral phosphine, solvent, base and benzalacetone weresimultaneously added in situ to a 50 ml stainless autoclave witha magnetic stirrer. Then, the autoclave was replaced with hydrogenthree times, and the hydrogen pressure was raised to desired level.The mixture was stirred at a predetermined temperature for presettime. After the reaction was completed, the conversion, chemical selectivity and enantioselectivity values were analyzed by GCand HPLC, respectively. The selectivity and ee values of unsaturatedalcohol were calculated from the equations chemical selectivity(UA, %) = UA/(SK + SA + UA) and enantioselectivity values(ee, %) = |R S|/|R + S|, respectively.
  • 99
  • [ 100-48-1 ]
  • [ 3160-40-5 ]
  • 4-(4-chlorophenyl)-4-(pyridin-4-yl)butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With pyridine; tetra-n-butylammonium acetate In dimethyl sulfoxide at 20℃; for 4h; Electrolysis;
52% With bis(acetylacetonato)nickel(II); tetra-n-butylammonium perchlorate; anhydrous sodium carbonate In 1,2-dichloro-ethane; acetonitrile at 50℃; for 3h;
  • 100
  • [ 104-88-1 ]
  • [ 67-63-0 ]
  • [ 3160-40-5 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate In water at 20℃; 2.4. Procedure for synthesis of β-aryl enals and enones General procedure: The β-aryl enals were synthesized by the following procedure.In a 50 mL round bottom (RB) flask, 2 mmol of benzaldehyde,9 mL ethanol (CH3CH2OH) and 3 mL water (H2O) was added in astoichiometric ratio of 3:1. After this, 2 equivalents of cesiumcarbonate (Cs2CO3) were added to the above mixture along with 25 mg of the synthesized CoCr2O4-HNT catalyst. The whole mixturewas then refluxed at 120 °C for 8 h. The reaction was monitoredthrough thin layer chromatography (TLC) and the productswere isolated through chromatography separation. Similarly, in a 50 mL RB flask b-aryl enones were synthesized bytaking the same amount of the substrate using 20 mg of CoCr2O4-HNT and in 1:3 ratio of H2O and ipr-OH (3 mL H2O + 9 mL ipr-OH).The reaction was stirred at room temperature for 4 h. After 4 h, thecatalyst was separated by normal filtration and the products wereseparated by chromatographic technique.
  • 101
  • [ 3160-40-5 ]
  • [ 875-79-6 ]
  • C17H16ClN [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With o-tetrachloroquinone; C24H39OPRu(1+)*BF4(1-); isopropyl alcohol In 1,2-dichloro-ethane at 125℃; for 36h; Glovebox; Schlenk technique; regioselective reaction;
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