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[ CAS No. 6315-96-4 ] {[proInfo.proName]}

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Product Details of [ 6315-96-4 ]

CAS No. :6315-96-4 MDL No. :MFCD00228290
Formula : C13H12O Boiling Point : -
Linear Structure Formula :- InChI Key :QLYPHTMKMPIJNG-UHFFFAOYSA-N
M.W :184.23 Pubchem ID :80587
Synonyms :

Safety of [ 6315-96-4 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P270-P273-P301+P312+P330-P501 UN#:
Hazard Statements:H302-H412 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6315-96-4 ]

* 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 [ 6315-96-4 ]

[ 6315-96-4 ] Synthesis Path-Downstream   1~81

  • 1
  • [ 613-46-7 ]
  • [ 925-90-6 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 2-naphthalenecarbonitrile; ethylmagnesium bromide In diethyl ether at 20 - 25℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether at 0 - 20℃;
With diethyl ether anschliessendes Behandeln mit Eis und wss. HCl und Kochen der erhaltenen wss. Loesung;
With toluene anschliessendes Behandeln mit Eis und wss. HCl und Kochen der erhaltenen wss. Loesung;
  • 3
  • [ 6315-96-4 ]
  • 3-[2]naphthyl-propionic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With yellow ammonium sulfide at 250 - 260℃; im geschlossenen Rohr;
  • 5
  • [ 91-20-3 ]
  • [ 79-03-8 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
98% With Aluminum Chloride In 1,2-dichloro-ethane at 35℃;
98% With Aluminum Chloride In 1,2-dichloro-ethane at 35℃; for 4h; 1-(2-Naphthyl)propanone (12). To a solution of propionyl chloride 11 (5.1 g, 55 mmol) and aluminum chloride (7.7 g, 58 mmol) in 1,2-dichloroethane (16 mL) was added dropwise a solution of naphthalene 10 (7.9 g, 62 mmol) in 1,2-dichloroethane (16 mL) over 3 h at 35° C. and it was allowed to stir for 1 h. The reaction was added 3MHCl solution at 0° C. and then separated a white solid. The filtrate was washed with water. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to furnish compound 12 (9.9 g, 98%) as a colorless oil, Rf=0.56 (hexane:EtOAc=9:1). 1H NMR (300 MHz, CDCl3): δ 8.58 (d, 1H, J=8.7 Hz), 7.94 (d, 1H, J=8.1 Hz), 7.86-7.80 (m, 2H), 7.59-7.42 (m, 3H), 3.04 (q, 2H, J=6.9 Hz), 1.27 (t, 3H, J=6.9 Hz). 13C NMR (75 MHz, CDCl3): δ 205.2, 136.0, 133.8, 132.2, 130.0, 128.3, 127.7, 127.1, 126.3, 125.7, 124.3, 35.2, 8.56. MS (EI): m/z 184.15 [M]+. HRMS (EI), calcd for C13H12O 184.0888, found [M]+ 184.0890.
76% With aluminium chloride anhydrous In nitrobenzene for 2h; 1.) room temp., 1 h, 2.) 35-40 deg. C, 1 h;
With aluminium chloride anhydrous; nitrobenzene
With Aluminum Chloride In dichloromethane at 30℃; for 5h; Inert atmosphere;

  • 6
  • [ 91-20-3 ]
  • [ 123-62-6 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride; nitrobenzene at -5 - 0℃;
  • 9
  • [ 6315-96-4 ]
  • [ 1779-49-3 ]
  • [ 75412-18-9 ]
YieldReaction ConditionsOperation in experiment
With phenyllithium In diethyl ether
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane Inert atmosphere; Stage #2: 1-(2-naphthyl)-1-propanone In tetrahydrofuran; hexane Inert atmosphere;
  • 10
  • [ 6315-96-4 ]
  • 1-(8-nitro-2-naphthyl)propan-1-one [ No CAS ]
  • 1-(5-nitro-2-naphthyl)propan-1-one [ No CAS ]
  • 1-(4-nitro-2-naphthyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(II) nitrate In acetic anhydride Ambient temperature; Yield given. Yields of byproduct given;
  • 11
  • [ 867-13-0 ]
  • [ 6315-96-4 ]
  • (Z)-3-Naphthalen-2-yl-pent-2-enoic acid ethyl ester [ No CAS ]
  • (E)-3-Naphthalen-2-yl-pent-2-enoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate In tetrahydrofuran at 0℃; for 19h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydride In tetrahydrofuran for 72h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 12
  • [ 6315-96-4 ]
  • [ 88738-78-7 ]
  • (Z)-3-Naphthalen-2-yl-pent-2-enoic acid methyl ester [ No CAS ]
  • (E)-3-Naphthalen-2-yl-pent-2-enoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate In dichloromethane at 0℃; for 18h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydride In tetrahydrofuran for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 13
  • [ 6315-96-4 ]
  • [ 1078-58-6 ]
  • (+)-1-(2-naphthyl)-1-phenylpropanol [ No CAS ]
  • 1-Naphthalen-2-yl-1-phenyl-propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With methanol; (1S)-(+)-3-exo-(dimethylamino)isoborneol In toluene for 48h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;
With methanol; (+)-3-exo-(dimethylamino)isoborneol In toluene for 48h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 14
  • [ 2356-16-3 ]
  • [ 6315-96-4 ]
  • (E)-2-Fluoro-3-naphthalen-2-yl-pent-2-enoic acid ethyl ester [ No CAS ]
  • (Z)-2-Fluoro-3-naphthalen-2-yl-pent-2-enoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 19 h; Yield given. Multistep reaction. Yields of byproduct given;
With sodium hydride In tetrahydrofuran 1.) 0 deg C, 2.) 0 deg C, 1 h; Yield given. Yields of byproduct given;
  • 15
  • [ 5888-29-9 ]
  • [ 6315-96-4 ]
  • (R)-3-Diethylamino-2-methyl-1-naphthalen-2-yl-propan-1-one [ No CAS ]
  • (S)-3-Diethylamino-2-methyl-1-naphthalen-2-yl-propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Al-Li-(R,R')-2,2'-dihydroxy-1,1'-binaphthyl; 3 A molecular sieve; lanthanum(lll) triflate In toluene at 50℃; for 18h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
  • 16
  • [ 69-65-8 ]
  • [ 6315-96-4 ]
  • (R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2-ethyl-2-naphthalen-2-yl-[1,3]dioxolan-4-yl]-ethane-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.2% With boron trifluoride diethyl etherate; orthoformic acid triethyl ester; zinc(II) chloride In N,N-dimethyl-formamide at 100℃; for 36h;
YieldReaction ConditionsOperation in experiment
With sulfur at 220℃;
  • 18
  • 1-naphthalen-2-yl-propan-1-one oxime [ No CAS ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
92% With KMnO4/alumina at 50℃; for 0.416667h;
  • 19
  • [ 6315-96-4 ]
  • [ 209065-57-6 ]
  • (E)-3-Naphthalen-2-yl-pent-2-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid With lithium hexamethyldisilazane In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-(2-naphthyl)-1-propanone In hexane; N,N-dimethyl-formamide at 0℃; for 25h;
  • 20
  • [ 75-77-4 ]
  • [ 6315-96-4 ]
  • [ 887334-39-6 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: chloro-trimethyl-silane; 1-(2-naphthyl)-1-propanone With sodium hydroxide In toluene for 12h; Heating; Stage #2: With triethylamine In toluene at 20℃;
  • 21
  • [ 580-13-2 ]
  • [ 3857-83-8 ]
  • [ 1067-52-3 ]
  • [ 91-20-3 ]
  • [ 612-78-2 ]
  • [ 1134-62-9 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
1: 17% 2: 10% 3: 4% 4: 2% In dimethyl sulfoxide at 100℃; for 14h;
  • 22
  • [ 3249-50-1 ]
  • [ 580-13-2 ]
  • [ 1067-52-3 ]
  • [ 91-20-3 ]
  • [ 612-78-2 ]
  • [ 1134-62-9 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
1: 65% 2: 8% 3: 4% 4: 1% In dimethyl sulfoxide at 100℃; for 14h;
1: 28% 2: 3% 3: 3% 4: 3% With tri-tert-butyl phosphine In dimethyl sulfoxide at 100℃; for 14h;
1: 16% 2: 15% 3: 9% 4: 3% With tris(2,4,6-trimethoxyphenyl)phosphine In dimethyl sulfoxide at 100℃; for 14h;
  • 23
  • [ 6315-96-4 ]
  • (R,R)-1-(β-naphthyl)-3-phenyl-3-hydroxy-2-methylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOH / toluene / 12 h / Heating 1.2: 95 percent / Et3N / toluene / 20 °C 2.1: Ga(OTf)3; (S,S)-4-tBu-2,6-bis[2-(HOPh2C-)pyrazolidin-1-ylmethyl]phenol / ethanol; H2O / 20 °C
  • 24
  • [ 6315-96-4 ]
  • (S,S)-1-(β-naphthyl)-3-phenyl-3-hydroxy-2-methylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOH / toluene / 12 h / Heating 1.2: 95 percent / Et3N / toluene / 20 °C 2.1: Ga(OTf)3; (S,S)-4-tBu-2,6-bis[2-(HOPh2C-)pyrazolidin-1-ylmethyl]phenol / ethanol; H2O / 20 °C
  • 25
  • [ 6315-96-4 ]
  • anti-1-(β-naphthyl)-3-phenyl-3-hydroxy-2-methylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOH / toluene / 12 h / Heating 1.2: 95 percent / Et3N / toluene / 20 °C 2.1: Ga(OTf)3; (S,S)-4-tBu-2,6-bis[2-(HOPh2C-)pyrazolidin-1-ylmethyl]phenol / ethanol; H2O / 20 °C
  • 26
  • [ 6315-96-4 ]
  • [ 107496-34-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: 1) lithium diisopropylamide / 1) ether, 0 deg C, 4 h, 2) -78 deg C, 2 h; 10 h, -78 deg C to RT 3: O3 / pentane / -78 °C
  • 27
  • [ 6315-96-4 ]
  • [ 76469-34-6 ]
YieldReaction ConditionsOperation in experiment
With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 16h; 3 Preparation 3: 2-Bromo-l-naphthalen-2-ylpropan-l-onel-Naphthalen-2-ylpropan-l-one (Preparation 2, 3.5g, 19.0mmol) was dissolved in THF(5OmL) followed by addition of PTAT (7.1g, 19.0mmol) and the reaction stirred at rt for 16hr. The solid was filtered and the filtrate concentrated in vacuo and purified on silica gel eluting EPO with EtOAc:hexanes (1:9) to afford the title compound, δϖ (CDCl3): 1.98 (3H, d), 5.47 (IH, q), 7.57 (IH, m), 7.63 (IH, m), 7.91 (2H, m), 7.99 (IH, d), 8.08 (IH, dd), 8.57 (IH, s).
With bromine In ethanol at 50 - 55℃; 4 Example 4 (Synthesis of 2-phenyl-4-(2-naphthyl)-5-methylimidazole) 46.0 g (0.288 mol) of bromine was added dropwise to a solution consisting of 55.8 g (0.303 mol) of 2-propionaphthone and 250 mL of ethanol at 50 to 55 °C. After completion of addition, the ethanol was distilled off in vacuo; and the resulting concentrate was dissolved in 130 mL of toluene, washed with a mixed aqueous solution of sodium bicarbonate and sodium chloride (200 mL x two times), and then dried over sodium sulfate to obtain a toluene solution of 2-bromo-2'-propionaphthone. A suspension consisting of 45.1 g (0.288 mol) of benzamidine hydrochloride, 119.4 g (0.864 mol) of potassium carbonate, and 240 mL of tetrahydrofuran was heated under reflux for one hour, and the foregoing toluene solution of 2-bromo-2'-propionaphthone was added dropwise over 40 minutes. After completion of addition, heating under reflux was continued for 2 hours. Next, the reaction mixture was concentrated in vacuo, the resulting concentrate was diluted with 200 mL of toluene, and the solution was poured into 600 mL of water. The mixture was stirred to precipitate a solid. This solid was collected by filtration, successively washed with toluene and water, and then dried to obtain a crude crystal as a desired material. This crude crystal was recrystallized from acetonitrile to obtain 55.0 g (yield: 67.2 %) of a white powder. The melting point, Rf value of thin layer chromatography, and NMR and mass spectral data of the resulting powder are as follows. . m.p.: 215 to 218 °C No. TLC (silica gel, acetone), Rf = 0.69 No. NMR (CDCl3) : No. 2.56 (s, 3H), 7.34 to 8.03 (m, 12H) No. MS m/z (%): 284 (M+, 100), 243 (1), 215 (2), 180 (14), 153 (12), 139 (9), 127 (4), 104 (7), 89 (5), 77 (7), 63 (5) From these spectral data, the resulting compound was identified as 2-phenyl-4-(2-naphthyl)-5-methylimidazole represented by the following formula.
With hydrogen bromide; bromine; acetic acid at 20℃; for 2h; 1.a Example 1: This example illustrates the preparation of 3-chloro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No.I.ae.198) a) Preparation of 2-bromo-1-naphthalen-2-yl-propan-1-one; Bromine (2.2 ml) is added to the mixture of 1-naphthalen-2-yl-propan-1-one (7.6 g), 0.1 ml of hydrobromic acid (48 % solution) and 100 ml of acetic acid at 0 °C under a nitrogen atmosphere. Subsequently, the mixture is stirred for 2.0 h at room temperature. The reaction mixture is evaporated under reduced pressure. After chromatography on silica gel, using a mixture of heptane / ethyl acetate 9 : 1 as eluent, 2-bromo-1-naphthalen-2-yl-propan-1-one is obtained as a yellow oil.
With phenyltrimethylammonium tribromide In chloroform at 20℃; Intermediate 52A 2-bromo-1-(2-naphthyl)propan-1-one To a solution of 1-(2-naphthyl)propan-1-one (Intermediate 51A, 10.30 g, 54.6 mmol) in chloro- form (200 ml) was added phenyltrimethylammonium tribromide (20.53 g, 54.6 mmol). After stir- ring overnight at room temperature, the reaction mixture was concentrated under reduced pres- sure. The residue was purified by flash-chromatography on silica gel (eluent: petroleum ether/ ethyl acetate 4:1) to give 12.50 g (82% of theory, 94% purity) of the title compound. LC/MS [Method 20]: Rt = 1.15 min; MS (ESIpos): m/z = 263/265 [M+H]+. 1H-NMR (300 MHz, DMSO-d6): d [ppm] = 8.79 (s, 1H), 7.97-8.20 (m, 4H), 7.62-7.76 (m, 2H), 6.01 (q, 1H), 1.85 (d, 3H).

  • 28
  • BrMg(1+)*C13H12N(1-) [ No CAS ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: BrMg(1+)*C13H12N(1-) With water; ammonium chloride In benzene Stage #2: With hydrogenchloride; water In benzene for 4h; Heating / reflux; 2 Reference Example 2 (Preparation of 2-propionaphthone) 50.8 g (0.33 mol) of 2-naphthonitrile was gradually added to a solution consisting of 164 g (0.5 mol) of a diethyl ether solution of magnesium ethyl bromide having a concentration of 3M and 120 ml of dry benzene, and after cease of heat generation, heating was started. About 100 mL of a distillate composed mainly of the diethyl ether was distilled off, 100 mL of benzene was added, and the mixture was heated under reflux for 3 hours. After completion of heating, the reaction mixture was cooled to room temperature; a solution consisting of 35 g (0.654 mol) of ammonium chloride and 140 mL of water was added; the aqueous layer was removed; 600 mL of 6N hydrochloric acid was added; and the mixture was heated under reflux for 4 hours. After cooling, the aqueous layer was removed; and the organic layer was washed with water, dried over sodium sulfate, and then evaporated to dryness in vacuo to obtain 57.3 g (yield: 94.2 %) of 2-propionaphthone as a dark yellow solid.
  • 29
  • [ 613-46-7 ]
  • [ 2386-64-3 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-naphthalenecarbonitrile; ethylmagnesium chloride In diethyl ether at 20℃; for 21h; Heating / reflux; Stage #2: With hydrogenchloride In diethyl ether; water 2 Preparation 2: l-Νaphthalen-2-ylpropan-l-one2-Naphthonitrile (3g, 19.6mmol) was dissolved in Et2O (2OmL) followed by addition of ethylmagnesium chloride (2.0M in Et2O, 9.8mL, 19.6mmol) and the reaction was heated to reflux for 5hr, then stirred at rt for 16hr. The reaction was quenched with 2N HCl (2OmL) and water (2OmL) then extracted into DCM (3 x 4OmL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with EtOAc:hexanes (1:9) to afford the title compound, δϖ (CDCl3): 1.30 (3H, t), 3.13 (2H, q), 7.57 (2H, m), 7.88 (2H, m), 7.96 (IH, d), 8.05 (IH, dd), 8.47 (IH, s).
  • 30
  • [ 925-90-6 ]
  • [ 113443-62-2 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether; ethyl acetate; Petroleum ether; ii) 58 ml (58 mmol) of a 1 M solution of ethylmagnesium bromide in tetrahydrofuran were added dropwise to a stirred solution of 12.5 g (58 mmol) of <strong>[113443-62-2]N,O-dimethyl 2-naphthalenecarbohydroxamate</strong> in 50 ml of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred overnight and then the reaction was quenched by the addition of water and diethyl ether. The ethereal layer was separated, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel using 33% ethyl acetate in petroleum ether for the elution to give 2.1 g of 1-(2-naphthyl)-1-propanone, NMR: (250 MHz, CDCl3) delta: 1.2-1.3 (t,3H), 3.1-3.2 (q,2H), 7.5-7.6 (m,2H), 7.8-8.1 (m,4H), 8.45 (s,1H).
  • 31
  • [ 6315-96-4 ]
  • 1-[2]naphthyl-propan-1-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride In pyridine 22.iii EXAMPLE 22 iii) A mixture of 2.1 g (11.41 mmol) of 1-(2-naphthyl)-1-propanone and 2.1 g (30.22 mmol) of hydroxylamine hydrochloride was heated under reflux in 30 ml of pyridine for 1 hour. The solution was evaporated to dryness and the residue was partitioned between water and diethyl ether. The organic layer was washed twice with 2M hydrochloric acid, dried over magnesium sulphate, filtered and evaporated to dryness to give 2.04 g of 1-(2-naphthyl)-1-propanone oxime as a pink solid, 1H NMR (400 MHz, CDCL3) δ: 1.2-1.3 (t,3H), 2.9-3.0 (q,2H), 7.45-7.55 (m,2H), 7.8-7.9 (m,4H), 8.02 (s,1H).
  • 32
  • [ 76635-88-6 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
99% With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; potassium carbonate In acetonitrile for 1h; Inert atmosphere; Reflux;
98% With Fe(II)(bis(2-(diisopropylphosphino)ethyl)amine)(CO)(H)(Cl); potassium-t-butoxide In toluene at 80℃; for 1h; Inert atmosphere;
87% With C13H21Cl2N3PRu(1+)*Cl(1-); potassium carbonate In tetrahydrofuran at 75℃; for 22h; Inert atmosphere; Sealed tube; General procedure for the catalytic isomerization of allylic alcohols using complex [RuCl2(η6-C6H6)(PTA-Me)] (3a) General procedure: In a sealed tube, under nitrogen atmosphere, the ruthenium complex [RuCl2( 6-C6H6)(PTA-Me)] (3a) (0.02-0.1 mmol; 0.5-2.5 mol% of Ru) and K2CO3 (0.05-0.25 mmol; 1.25-6.25 mol%) were added to a solution of the corresponding allylic alcohol 4a-o (4 mmol) in tetrahydrofuran (4 mL), and the resulting mixture stirred at 75 °C for the indicated time (see Table 4 and Scheme 3). The course of the reaction was monitored by taking regularly samples of ca. 10 L which after dilution with dichloromethane (3 mL) were analyzed by GC. After the reaction was finished, the mixture was cooled to room temperature leading to the partial precipitation of 3a. The solid was separated by filtration and the reaction product isolated by solvent removal and chromatographic workup of the residue on silica-gel using a mixture of EtOAc-hexane (1:10) as eluent. The identity of the resulting carbonyl compounds 5a-o was assessed by comparison of their retention times with those of commercially available pure samples (Sigma-Aldrich or Acros Organics), by their fragmentation in GC/MS, and/or NMR spectroscopy.
83% With potassium-t-butoxide In dimethyl sulfoxide at 70℃; for 1h; Inert atmosphere; Sealed tube;
80% With 1,10-Phenanthroline; sodium tertiary butoxide In toluene at 80℃; for 2h; Inert atmosphere;

  • 33
  • C15H16O [ No CAS ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water In ethylene glycol for 0.5h;
  • 34
  • [ 2033-24-1 ]
  • [ 6315-96-4 ]
  • [ 1186309-76-1 ]
YieldReaction ConditionsOperation in experiment
14% Stage #1: cycl-isopropylidene malonate; 1-(2-naphthyl)-1-propanone With titanium(IV) chloride tetrahydrofuran In tetrahydrofuran; dichloromethane at 0℃; Inert atmosphere; Stage #2: With pyridine In tetrahydrofuran; dichloromethane at 0 - 20℃; Inert atmosphere;
  • 35
  • [ 6315-96-4 ]
  • [ 154667-96-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(2-naphthyl)-1-propanone With ammonium acetate; sodium cyanoborohydride In methanol at 23℃; for 24h; Stage #2: With hydrogenchloride In methanol; water Stage #3: With potassium hydroxide In water
With methanol; ammonium acetate; sodium cyanoborohydride at 23℃; for 24h; 2-Methyl-N-[1-(2-naphthyl)propyl]benzamide (14). To a solution of ketone 12 (2.1 g, 11.4 mmol) in MeOH (50 mL) was added ammonium acetate (8.8 g, 0.11 mol) and NaBH3CN (528 mg, 8.0 mmol) at 23° C. and was stirred for 24 h. Conc. HCl was added until pH<2, and the solvent was removed under reduced pressure. The residue was taken up in water (15 mL) and extracted once with Et2O. The aqueous layer was brought to pH>12 with solid KOH and extracted with CH2Cl2. The organic layers were dried over Na2SO4 and concentrated under reduced pressure to give amine 13 as crude compound, MS (EI): m/z 185.20 [M]+. HRMS (EI), calcd for C13H15N 185.1204, found [M]+ 185.1206. The general coupling procedure was carried out with amine 13 (50 mg, mmol) and o-toluic acid (37.5 mg, mmol) to give inhibitor 14 (21 mg, 2 steps 26%) as a white solid, Rf=0.25 (hexane:EtOAc=3:1). 1HNMR (300 MHz,CDCl3): δ 7.84-7.78(m, 4H), 7.49-7.44 (m, 3H), 7.35-7.26 (m, 2H), 7.20-7.14 (m, 2H), 6.12 (d,1H, J=8.4 Hz), 5.28-5.20 (m, 1H), 2.39 (s, 3H), 2.04-1.95 (m, 2H), 0.99 (t, 3H, J=7.2 Hz). 13C NMR (75 MHz, CDCl3): δ 169.4, 139.4, 136.6, 136.0, 133.3, 132.7, 130.9, 129.8, 128.5, 127.8, 127.6, 126.5, 126.2, 125.8, 125.7, 125.3, 124.7, 55.2, 29.1, 19.7, 10.9. MS (EI): m/z 303.25 [M]+. HRMS (EI), calcd for C21H21NO 303.1623, found [M]+ 303.1624.
  • 36
  • [ 6315-96-4 ]
  • 1-naphthalen-2-yl-propan-1-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;
  • 37
  • [ 132154-59-7 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
98% With Dess-Martin periodane In dichloromethane at 20℃; Intermediate 51A 1-(2-naphthyl)propan-1-one To a solution of 1-(2-naphthyl)propan-1-ol (Intermediate 50A, 10.50 g, 55.3 mmol) in dichloro- methane (200 ml) was added Dess-Martin periodinane (46.86 g, 110.5 mmol). After stirring over- night at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash-chromatography on silica gel (eluent: petroleum ether/ethyl acetate 7:3) to give 10.30 g (98% of theory) of the title compound. LC/MS [Method 20]: Rt = 1.08 min; MS (ESIpos): m/z = 185 [M+H]+. 1H-NMR (300 MHz, DMSO-d6): d [ppm] = 8.68 (s, 1H), 8.13 (d, 1H), 7.97-8.04 (m, 3H), 7.59-7.70 (m, 2H), 3.20 (q, 2H), 1.15 (t, 3H).
90% With pyridinium chlorochromate In dichloromethane for 3h; Inert atmosphere;
With sodium dichromate; sulfuric acid In dimethyl sulfoxide
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate Reflux;

  • 38
  • C15H16O [ No CAS ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water In ethylene glycol Inert atmosphere;
  • 39
  • [ 6315-96-4 ]
  • [ 69739-34-0 ]
  • [ 1231952-07-0 ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;
  • 40
  • [ 6315-96-4 ]
  • [ 64-19-7 ]
  • [ 1269487-00-4 ]
YieldReaction ConditionsOperation in experiment
63% With tetrabutylammomium bromide In water at 110℃; for 24h; Inert atmosphere;
  • 41
  • [ 132154-59-7 ]
  • [ 90-13-1 ]
  • [ 91-20-3 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
1: > 99 %Spectr. 2: 0.47 mmol With morpholine; bis(1,5-cyclooctadiene)nickel(0); potassium phosphate; trimethylphosphane In tetrahydrofuran; 1,4-dioxane at 100℃; for 2h; Inert atmosphere;
  • 42
  • [ 6315-96-4 ]
  • [ 104-15-4 ]
  • (R)-1-(naphthalen-2-yl)-1-oxopropan-2-yl 4-methylbenzenesulfonate [ No CAS ]
  • (S)-1-(naphthalen-2-yl)-1-oxopropan-2-yl 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C17H15I; 3-chloro-benzenecarboperoxoic acid In ethyl acetate at 20℃; for 24h; enantioselective reaction;
61 % ee With (R)-2-(tert-butylsulfonyl)-6-chloro-2′-iodo-1,1′-biphenyl; 3-chloro-benzenecarboperoxoic acid In ethyl acetate at 20℃; for 72h; Inert atmosphere; Overall yield = 69%; Overall yield = 24.5mg; enantioselective reaction;
78 % ee With methyl N-(2-iodo-4,6-dimethylphenyl)-N-tosylalaninate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; ethyl acetate at 20℃; for 72h; Overall yield = 48 percent; Overall yield = 46 mg; stereoselective reaction;
67 % ee With methyl N-(2-iodo-4,6-dimethylphenyl)-N-tosylalaninate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; for 72h; Overall yield = 60 percent; Overall yield = 58 mg; stereoselective reaction;

  • 43
  • [ 552-16-9 ]
  • [ 6315-96-4 ]
  • [ 57221-66-6 ]
YieldReaction ConditionsOperation in experiment
70% With 3-methyl-2-nitrophenol; palladium diacetate; Tetrabutylammonium hydrogen diacetate; silver carbonate; tricyclohexylphosphine In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;
  • 44
  • [ 580-13-2 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux
Multi-step reaction with 2 steps 1: magnesium; iodine / tetrahydrofuran 2: palladium diacetate; tert.-butylhydroperoxide; toluene-4-sulfonic acid / water; acetonitrile / 6 h / 20 °C
  • 45
  • [ 100-97-0 ]
  • [ 6315-96-4 ]
  • [ 92253-90-2 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride at 80℃; for 5h; Inert atmosphere;
  • 46
  • [ 6315-96-4 ]
  • (R)-2-methyl-1-(naphthalen-2-yl)prop-2-en-1-ol [ No CAS ]
  • (1R)-2-methyl-1-(naphthalen-2-yl)allyl propionate [ No CAS ]
  • (1S)-2-methyl-1-(naphthalen-2-yl)allyl propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetic anhydride / 5 h / 80 °C / Inert atmosphere 2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 °C / Inert atmosphere 3.1: Fc-PIP; N-ethyl-N,N-diisopropylamine / toluene / 0.08 h / 0 °C 3.2: 0 °C
  • 47
  • [ 6315-96-4 ]
  • (1R)-2-methyl-1-(naphthalen-2-yl)allyl propionate [ No CAS ]
  • (1S)-2-methyl-1-(naphthalen-2-yl)allyl propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic anhydride / 5 h / 80 °C / Inert atmosphere 2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 °C / Inert atmosphere 3: dmap / dichloromethane / 20 °C 4: Daicel CHIRALCEL OD-H / methanol; hexane; isopropyl alcohol / 20 °C / Resolution of racemate
  • 48
  • [ 6315-96-4 ]
  • 2-methyl-1-(naphthalen-2-yl)allyl propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic anhydride / 5 h / 80 °C / Inert atmosphere 2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 °C / Inert atmosphere 3: dmap / dichloromethane / 20 °C
  • 49
  • [ 6315-96-4 ]
  • 2-methyl-1-(naphthalen-2-yl)prop-2-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / 5 h / 80 °C / Inert atmosphere 2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 °C / Inert atmosphere
  • 50
  • [ 6315-96-4 ]
  • [ 557-20-0 ]
  • (R)-1-(2-naphthyl)propanol [ No CAS ]
  • (S)-1-(2-naphthyl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(2-naphthyl)-1-propanone With titanium(IV) isopropylate; (S)-3,3'-bis(4-phenyl-1H-1,2,3-triazol-1-yl)-[1,1'-binaphthalene]-2,2'-diol In toluene at 20 - 25℃; for 0.5h; Inert atmosphere; Stage #2: diethylzinc In toluene at 20 - 25℃; for 19h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 51
  • [ 554-14-3 ]
  • [ 6315-96-4 ]
  • [ 1440663-71-7 ]
YieldReaction ConditionsOperation in experiment
86% With silver (II) carbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium acetate; palladium diacetate; tricyclohexylphosphine In 1,2-dimethoxyethane at 100℃; for 24h; Schlenk technique; Inert atmosphere; (E)-3-(5-methylthiophen-2-yl)-1-(naphthalen-2-yl)prop-2-en-1-one General procedure: In a glove box, a 25 mL of Schlenk tube equipped with a stir bar was charged with Pd(OAc)2 (0.03 mmol, 0.1 equiv), PCy3 (0.03 or 0.06 mmol, 0.1 or 0.2 equiv), LiOAc (0.45 mmol, 1.5 equiv) (or NaOAc), TEMPO (0.12 mmol, 0.4 equiv), Ag2CO3 (0.9 mmol, 3 equiv). The tube was fitted with a rubber septum and removed out of the glove box. DME (2 mL), propiophenone (0.9 mmol, 3.0 equiv) and thiophene (0.3 mmol, 1.0 equiv) were added in turn to the Schlenk tube through the rubber septum using syringes, and then the septum was replaced with a Teflon screwcap under nitrogen flow (if the thiophene or the substituted propiophenone was solid, it was added to the tube in the glove box). The reaction mixture was stirred at 100 oC or 120 oC for 24 h. After cooling down, the reaction mixture was diluted with 10 mL of ethyl ether, filtered through a pad of silica gel, followed by washing the pad of the silica gel with the same solvent (20 mL), concentrated under reduced pressure. The residue was then purified by flash chromatography on silica gel with 2-15 % ethyl ether in petroleum ether as eluent to provide the corresponding product.
  • 52
  • [ 6315-96-4 ]
  • [ 98-95-3 ]
  • [ 873411-80-4 ]
YieldReaction ConditionsOperation in experiment
64% With sodium t-butanolate In dimethyl sulfoxide at 25℃; for 0.5h; Inert atmosphere; regiospecific reaction;
  • 53
  • [ 33513-42-7 ]
  • [ 93-08-3 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
61% With ammonium peroxydisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 110℃; for 3h; Inert atmosphere; Sealed tube;
  • 54
  • [ 6315-96-4 ]
  • [ 104-94-9 ]
  • C20H19NO [ No CAS ]
  • C20H19NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
82 % de In benzene at 20 - 80℃; for 120h; Molecular sieve; Inert atmosphere; Overall yield = 41 %;
  • 55
  • [ 64-17-5 ]
  • [ 76635-88-6 ]
  • [ 7270-98-6 ]
  • [ 6315-96-4 ]
  • (R)-1-(2-naphthyl)propanol [ No CAS ]
  • (S)-1-(2-naphthyl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
83 % ee With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium <i>tert</i>-butylate; lithium chloride; Boc-L-alanine(2S)-hydroxypropylamide In tetrahydrofuran at 40℃; for 18h; Inert atmosphere; enantioselective reaction;
  • 56
  • [ 66-99-9 ]
  • [ 7270-98-6 ]
  • [ 6315-96-4 ]
  • (R)-1-(2-naphthyl)propanol [ No CAS ]
  • (S)-1-(2-naphthyl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; Boc-L-alanine(2S)-hydroxypropylamide; lithium chloride; potassium <i>tert</i>-butylate / tetrahydrofuran / 18 h / 40 °C / Inert atmosphere
  • 57
  • [ 67-56-1 ]
  • [ 6315-96-4 ]
  • [ 107574-57-2 ]
YieldReaction ConditionsOperation in experiment
80% With C34H27IrN2P(1+)*C32H12BF24(1-); caesium carbonate at 65℃; for 24h; Inert atmosphere;
74% With C34H27MnNO3P2(1+)*Br(1-); caesium carbonate at 85℃; for 24h; Schlenk technique; Inert atmosphere;
  • 58
  • [ 2489-87-4 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
89% With tert.-butylhydroperoxide; palladium diacetate; toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 6h; chemoselective reaction;
  • 59
  • Zn(2+)*Li(1+)*2C3H7(1-)*C5H11(1-) [ No CAS ]
  • [ 93-09-4 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: naphthalene-2-carboxylate With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: Zn(2+)*Li(1+)*2C3H7(1-)*C5H11(1-) In 1,4-dioxane at 50℃; for 18h; Schlenk technique; Inert atmosphere; chemoselective reaction;
  • 60
  • Zn(2+)*Li(1+)*2C3H7(1-)*C5H11(1-) [ No CAS ]
  • [ 93-09-4 ]
  • [ 33489-63-3 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
1: 71 %Spectr. 2: 11 %Spectr. Stage #1: naphthalene-2-carboxylate With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: Zn(2+)*Li(1+)*2C3H7(1-)*C5H11(1-) In 1,4-dioxane at 50℃; for 18h; Schlenk technique; Inert atmosphere; chemoselective reaction;
  • 61
  • [ 66-99-9 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1.25 h / 5 - 20 °C 2: sodium tertiary butoxide; 1,10-Phenanthroline / toluene / 2 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 2 h / -78 - 20 °C 2: Dess-Martin periodane / dichloromethane / 20 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran / Inert atmosphere; Cooling with ice 2: pyridinium chlorochromate / dichloromethane / 3 h / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2: potassium-t-butoxide / dimethyl sulfoxide / 1 h / 70 °C / Inert atmosphere; Sealed tube

  • 62
  • [ 6315-96-4 ]
  • [ 100-58-3 ]
  • (R)-1-(2-naphthalenyl)-1-phenylpropanol [ No CAS ]
  • (+)-(S)-1-(naphthalen-2-yl)-1-phenylpropan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 % ee With (R)-3,3'-bis(3,3-dimethylbutyl)-2,2'-dihydroxy-1,1'-binaphthyl In tetrahydrofuran; diethyl ether at -45℃; Inert atmosphere; Overall yield = 97 %; enantioselective reaction;
  • 63
  • [ 6315-96-4 ]
  • C11H15OZn [ No CAS ]
  • C21H20O [ No CAS ]
  • C21H20O [ No CAS ]
YieldReaction ConditionsOperation in experiment
89 % ee Stage #1: C11H15OZn With titanium(IV) isopropylate; dimethyl zinc(II); (1S,2R,4R,1'R,2'R,1''S,2''R,4''R)-N-{trans-2'-[2''-hydroxy-7'',7''-dimethylbicyclo[2.2.1]hept-1''-ylmethylsulfonamino]cyclohexyl}-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethanesulfonamide In toluene at -78 - 20℃; Inert atmosphere; Stage #2: 1-(2-naphthyl)-1-propanone at 0 - 20℃; for 16h; Inert atmosphere; enantioselective reaction;
  • 64
  • [ 6315-96-4 ]
  • [ 1670-14-0 ]
  • 4-(naphthalen-2-yl)-2-phenylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With [2,2]bipyridinyl; TEMPOL; copper diacetate; sodium acetate In 1,2-dichloro-benzene at 140℃; for 24h; Sealed tube;
  • 65
  • [ 6315-96-4 ]
  • [ 149-73-5 ]
  • [ 57421-64-4 ]
YieldReaction ConditionsOperation in experiment
83% With trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene at 20℃; for 5h;
  • 66
  • [ 6315-96-4 ]
  • [ 149-73-5 ]
  • [ 119393-06-5 ]
  • [ 222722-14-7 ]
YieldReaction ConditionsOperation in experiment
24 % ee With trifluorormethanesulfonic acid; (2,6-bis(((R)-1-(mesitylamino)-1-oxopropan-2-yl)oxy)-phenyl)-λ3-iodanediyl diacetate at -20℃; for 48h; Overall yield = 52 %; Overall yield = 30 mg; stereoselective reaction;
  • 67
  • [ 271-58-9 ]
  • [ 6315-96-4 ]
  • naphthalen-2-yl(quinolin-3-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In 1,2-dichloro-benzene at 110℃; for 12h; Molecular sieve; Inert atmosphere;
  • 68
  • [ 85-47-2 ]
  • [ 6315-96-4 ]
  • 1-(naphthalen-2-yl)-1-oxopropan-2-yl-naphthalene-1-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With (R)-2-(tert-butylsulfonyl)-6-chloro-2′-iodo-1,1′-biphenyl; 3-chloro-benzenecarboperoxoic acid In ethyl acetate at 20℃; for 72h; Inert atmosphere; enantioselective reaction;
  • 69
  • [ 838-85-7 ]
  • [ 6315-96-4 ]
  • (R)-1-(naphthalen-2-yl)-1-oxopropan-2-yl diphenyl phosphate [ No CAS ]
  • (S)-1-(naphthalen-2-yl)-1-oxopropan-2-yl diphenyl phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57 % ee With (R)-2-(tert-butylsulfonyl)-6-chloro-2′-iodo-1,1′-biphenyl; 3-chloro-benzenecarboperoxoic acid In ethyl acetate at 20℃; for 72h; Inert atmosphere; Overall yield = 55%; Overall yield = 23.6 mg; enantioselective reaction;
  • 70
  • [ 97-94-9 ]
  • [ 82408-29-5 ]
  • [ 6315-96-4 ]
YieldReaction ConditionsOperation in experiment
89% With bis(1,5-cyclooctadiene)nickel (0); caesium carbonate; tricyclohexylphosphine In hexane; toluene at 40℃; for 16h; Sealed tube; Glovebox; chemoselective reaction;
  • 71
  • [ 811-98-3 ]
  • [ 6315-96-4 ]
  • 2-methyl-1-(naphthalen-2-yl)propan-1-one-2,3,3,3-d<SUB>4</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With C34H27MnNO3P2(1+)*Br(1-); caesium carbonate at 105℃; for 24h; Schlenk technique; Inert atmosphere;
  • 72
  • [ 6315-96-4 ]
  • 3-(naphthalen-2-yl)pent-1-yn-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 1.2: 2.17 h / -78 - 20 °C / Inert atmosphere 2.1: potassium carbonate; water / methanol / 0.5 h / 0 - 20 °C
  • 73
  • [ 6315-96-4 ]
  • 3-(naphthalen-2-yl)hexa-4,5-dien-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 1.2: 2.17 h / -78 - 20 °C / Inert atmosphere 2.1: potassium carbonate; water / methanol / 0.5 h / 0 - 20 °C 3.1: diisopropylamine; copper(l) iodide / 1,4-dioxane / 20 h / 110 °C / Inert atmosphere
  • 74
  • [ 6315-96-4 ]
  • (S)-3-(naphthalen-2-yl)hexa-4,5-dien [ No CAS ]
  • 3-(naphthalen-2-yl)hexa-4,5-dien [ No CAS ]
  • C16H16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 1.2: 2.17 h / -78 - 20 °C / Inert atmosphere 2.1: potassium carbonate; water / methanol / 0.5 h / 0 - 20 °C 3.1: diisopropylamine; copper(l) iodide / 1,4-dioxane / 20 h / 110 °C / Inert atmosphere 4.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine / 0.17 h / 20 °C / Inert atmosphere; Sealed tube 4.2: 100 h / 20 °C / Inert atmosphere; Sealed tube
  • 75
  • [ 6315-96-4 ]
  • [ 1066-54-2 ]
  • C18H22OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: 1-(2-naphthyl)-1-propanone In tetrahydrofuran; hexane at -78 - 20℃; for 2.16667h; Inert atmosphere;
  • 76
  • [ 6315-96-4 ]
  • [ 100-58-3 ]
  • (E)-2-(1-phenylprop-1-en-1-yl)naphthalene [ No CAS ]
  • 2-(1-phenylprop-1-en-1-yl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.667 % de Stage #1: 1-(2-naphthyl)-1-propanone With lithium diisopropyl amide In tetrahydrofuran for 1h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique; Stage #2: phenylmagnesium bromide With bis(1,5-cyclooctadiene)nickel (0); magnesium bromide; tricyclohexylphosphine In diethyl ether; toluene at 70℃; for 24h; Inert atmosphere; Sealed tube; Schlenk technique; Overall yield = 75 %; Overall yield = 36.7 mg; diastereoselective reaction;
  • 77
  • [ 111-26-2 ]
  • [ 6315-96-4 ]
  • [ 107-21-1 ]
  • C21H25N [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With C34H27MnNO3P2(1+)*Br(1-); potassium <i>tert</i>-butylate In tert-Amyl alcohol at 135℃; for 24h;
  • 78
  • [ 5344-90-1 ]
  • [ 6315-96-4 ]
  • 3-methyl-2-(naphthalene-2′-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With potassium <i>tert</i>-butylate In 1,4-dioxane at 90℃; Inert atmosphere;
  • 79
  • [ 5344-90-1 ]
  • [ 6315-96-4 ]
  • (2S,3R)-3-methyl-2-(naphthalen-2-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / 1,4-dioxane / 90 °C / Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C43H45NO2P2; hydrogen / 1,4-dioxane / 24 h / 25 °C / 7500.75 Torr / Schlenk technique; Autoclave
  • 80
  • [ 6315-96-4 ]
  • diethyl 4-methyl-1-[1-(2-naphthyl)-1-oxopropan-2-yl]-1H-pyrazole-3,5-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phenyltrimethylammonium tribromide / chloroform / 20 °C 2: potassium carbonate / acetone / 20 °C
  • 81
  • [ 6315-96-4 ]
  • ethyl 3,7-dimethyl-6-(2-naphthyl)-4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: phenyltrimethylammonium tribromide / chloroform / 20 °C 2: potassium carbonate / acetone / 20 °C 3: acetic acid; ammonium acetate / 18 h / 110 °C
Same Skeleton Products
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