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Chemical Structure| 627906-96-1
Chemical Structure| 627906-96-1
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Product Details of [ 627906-96-1 ]

CAS No. :627906-96-1 MDL No. :MFCD28122664
Formula : C15H17BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PYUGEXFBFIGNIR-UHFFFAOYSA-N
M.W : 240.11 Pubchem ID :66552877
Synonyms :

Safety of [ 627906-96-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 627906-96-1 ]

* 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 [ 627906-96-1 ]

[ 627906-96-1 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 97802-08-9 ]
  • [ 627906-96-1 ]
  • [ 479417-38-4 ]
  • 3
  • 1-(3-chlorophenyl)-3-triethylsilyl-2-propyn-1-one [ No CAS ]
  • [ 627906-96-1 ]
  • C25H27OSiCl [ No CAS ]
  • 4
  • 1-phenyl-3-(triethylsilyl)prop-2-yn-1-one [ No CAS ]
  • [ 627906-96-1 ]
  • C25H28OSi [ No CAS ]
  • 5
  • [ 83813-73-4 ]
  • [ 627906-96-1 ]
  • [ 827-54-3 ]
  • 6
  • [ 185739-14-4 ]
  • [ 627906-96-1 ]
  • [ 131581-40-3 ]
  • 7
  • [ 455-67-4 ]
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  • 9
  • [ 668987-38-0 ]
  • [ 7385-85-5 ]
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  • 10
  • [ 1253579-22-4 ]
  • [ 627906-96-1 ]
  • C37H26FNO2 [ No CAS ]
  • C37H26FNO2 [ No CAS ]
  • 11
  • [ 93-44-7 ]
  • [ 201733-56-4 ]
  • [ 135-19-3 ]
  • [ 627906-96-1 ]
  • 12
  • [ 15300-41-1 ]
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  • [ 3839-35-8 ]
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  • [ 2876-46-2 ]
  • 15
  • [ 32316-92-0 ]
  • [ 126-30-7 ]
  • [ 627906-96-1 ]
YieldReaction ConditionsOperation in experiment
With magnesium sulfate; In tetrahydrofuran; at 20℃;Inert atmosphere; The dry THF (1 mL) solution of organoboronic acid (10 mmol), 2,2-dimethylpropan-1,3-diol (11 mmol, 1.2g), and MgSO4 (14 mmol, 1.7 g) mixture was stirred overnight at room temperature under Ar. The crude mixture was concentrated under a reduced pressure and neopentyl borate ester derivative (2) was purified on a silica gel column with yields varying in the range of 76-97% (hexane/ethyl acetate as the eluent).
In diethyl ether; at 20℃;Inert atmosphere; Molecular sieve; General procedure: To a Et2O solution of anorganoboronic acid (1.00 equiv) and 2,2-dimethylpropane-1,3-diol (neopentyl glycol)(1.02 equiv), 4A molecular sieves was added and the reaction mixture was stirred atroom temperature. After the reaction finished, the reaction mixture was filtered andconcentrated in vacuo. The residue was subjected to flash column chromatography(eluent: petroleum ether/ethyl acetate) or recrystallization to obtain the desired product
  • 16
  • [ 273-53-0 ]
  • [ 627906-96-1 ]
  • [ 14625-56-0 ]
  • 17
  • diethyl 3-phenylprop-2-enyl phosphate [ No CAS ]
  • [ 627906-96-1 ]
  • [ 949568-49-4 ]
  • 18
  • [ 627906-96-1 ]
  • [ 768392-27-4 ]
  • [ 1334512-10-5 ]
  • 20
  • [ 92197-18-7 ]
  • [ 627906-96-1 ]
  • [ 92596-72-0 ]
  • 21
  • [ 583-55-1 ]
  • [ 627906-96-1 ]
  • [ 22082-97-9 ]
YieldReaction ConditionsOperation in experiment
87% General procedure: To a solution of Pd(OAc)2 (101 mg, 0.45 mmol ), PPh3 (354 mg, 1.35 mmol), K2CO3 (2.76 g, 20.0 mmol) in DME (30 mL) and H2O (10 mL) at room temperature under argon was added 9c (3.0 g, 11 mol). The resulting solution was stirred for 10 min, then 8 (2.83 g, 10.0 mmol) was added, and the solution was heated at reflux for 23 h and monitored by TLC. The resulting solution was cooled to room temperature, EtOAc (100 mL) was added, and the solution was washed with a saturated brine solution and water, and dried over anhydrous Na2SO4. Following evaporation of the solvent under reduced pressure, the residue was purified by chromatography on a silica gel column eluted with hexane/EtOAc (150:1) to yield 10c (2.84 g, 91%).
  • 22
  • [ 4897-68-1 ]
  • [ 627906-96-1 ]
  • [ 1393793-79-7 ]
YieldReaction ConditionsOperation in experiment
78% General procedure: To a solution of Pd(OAc)2 (101 mg, 0.45 mmol ), PPh3 (354 mg, 1.35 mmol), K2CO3 (2.76 g, 20.0 mmol) in DME (30 mL) and H2O (10 mL) at room temperature under argon was added 9c (3.0 g, 11 mol). The resulting solution was stirred for 10 min, then 8 (2.83 g, 10.0 mmol) was added, and the solution was heated at reflux for 23 h and monitored by TLC. The resulting solution was cooled to room temperature, EtOAc (100 mL) was added, and the solution was washed with a saturated brine solution and water, and dried over anhydrous Na2SO4. Following evaporation of the solvent under reduced pressure, the residue was purified by chromatography on a silica gel column eluted with hexane/EtOAc (150:1) to yield 10c (2.84 g, 91%).
  • 23
  • [ 627906-96-1 ]
  • [ 50-32-8 ]
  • 24
  • [ 116-14-3 ]
  • [ 627906-96-1 ]
  • 2-(1,2,2-trifluoroethenyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
67%Spectr. With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In tetrahydrofuran; tetrahydrofuran-d8; at 100℃; for 20h;Inert atmosphere; Example 29 [0314] In a glove box, a THF (0.4 mL)-THF-D8 (0.1 mL) solution of Pd2(dba)3 (5 mg, 0.005 mmol), PCy3 (5.6 mg, 0.02 mmol), and <strong>[627906-96-1]2-(2-naphthyl)-5,5-dimethyl-1,3,2-dioxaborinane</strong> (24.0 mg, 0.1 mmol) was prepared in a pressure tube (capacity: 2 mL) under an inert atmosphere. α,α,α-Trifluorotoluene (12 μL, 0.097 mmol: internal standard for the 19F-NMR measurement) was added thereto. TFE (0.313 mmol: calculated from the container capacity described above and the applied pressure of 0.35 MPa) was further added thereto. This reaction solution was allowed to stand at 100 C. for 20 hours. The reaction was monitored by 19F-NMR. Based on the internal standard, it was confirmed that 2-(1,2,2-trifluoroethenyl)naphthalene was obtained at a yield of 67%.
70%Spectr. General procedure: The reactions were conducted with a pressure-tight NMR tube (Wilmad-LabGlass, 524-PV-7). To a solution of CuOtBu (2.7 mg, 0.02 mmol) and ligand in THF/THF-d8 (v/v’ = 4/1) (0.5 mL) was added arylboronic acids (0.022 mmol, 1.1 eq) and α,α,α-trifluorotoluene (2.4 L, 0.02 mmol; as an internal standard for 19F NMR). The resultant solution was transferred into the tube, and then TFE (3.5 atm, excess) was pressurized. After the reaction mixture was heated at 40 C for 24 h, Lewis acid (0.04 mmol, 2.0 eq) was added. Monitoring the reaction was performed by means of 19F NMR spectroscopy. The yields were determined by 19F NMR spectroscopy using α,α,α-trifluorotoluene as an internal standard.
  • 25
  • [ 1025506-03-9 ]
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  • [ 1439838-42-2 ]
  • 27
  • [ 627906-96-1 ]
  • [ 768392-43-4 ]
  • [ 1334512-29-6 ]
  • 29
  • [ 100712-92-3 ]
  • [ 201733-56-4 ]
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  • 30
  • [ 73540-76-8 ]
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  • [ 1415045-47-4 ]
  • 31
  • [ 88132-08-5 ]
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  • [ 1415045-60-1 ]
  • 32
  • [ 51674-10-3 ]
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  • [ 1415045-60-1 ]
  • 34
  • [ 2984-50-1 ]
  • [ 627906-96-1 ]
  • 1-(naphthalen-2-yl)octan-2-ol [ No CAS ]
  • 35
  • [ 96-09-3 ]
  • [ 627906-96-1 ]
  • 2-(naphthalen-2-yl)-1-phenylethanol [ No CAS ]
  • 36
  • [ 1503-86-2 ]
  • [ 201733-56-4 ]
  • [ 627906-96-1 ]
YieldReaction ConditionsOperation in experiment
75% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; P(p-CH3OC6H4)3; In toluene; at 130℃; for 15h;Inert atmosphere;Catalytic behavior; General procedure: [RhCl(cod)]2 (12 mg, 0.025 mmol), P(4-MeOC6H4)3 (53 mg, 0.15 mmol), B2(nep)2 (113 mg, 0.50mmol), 1a (110 mg, 0.50 mmol) and toluene (0.50 mL) were added to a 10 mL two-necked flask under a stream of nitrogen. The mixture was stirred at 130 C for 3 h, and then cooled to room temperature. Additional [RhCl(cod)]2 (12 mg, 0.025 mmol), P(4-MeOC6H4)3 (53 mg, 0.15 mmol)and B2(nep)2 (113 mg, 0.50 mmol) were added under a stream of nitrogen, and the mixture was heated at 130 C for 12 h. The mixture was cooled to room temperature and passed through NH silica to remove remaining 1a and phosphine ligand (eluent: hexane/EtOAc = 1/0 to 50/1, then EtOAc/MeOH = 10/1). The obtained crude product was further purified by flash column chromatography over SiO2 (eluent: hexane/EtOAc = 20/1 to 10/1) to give 5,5-dimethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborinane (2) [CAS: 22871-77-8] as a white solid (90mg, 75%).
  • 38
  • [ 93-18-5 ]
  • [ 201733-56-4 ]
  • [ 91-20-3 ]
  • [ 627906-96-1 ]
YieldReaction ConditionsOperation in experiment
1: 69 %Chromat. 2: 32 %Chromat. With bis(1,5-cyclooctadiene)nickel (0); sodium formate; tricyclohexylphosphine In toluene at 95℃; for 15h; Inert atmosphere;
  • 39
  • [ 613-62-7 ]
  • [ 201733-56-4 ]
  • [ 91-20-3 ]
  • [ 627906-96-1 ]
YieldReaction ConditionsOperation in experiment
1: 19 %Chromat. 2: 9 %Chromat. With bis(1,5-cyclooctadiene)nickel (0); sodium formate; tricyclohexylphosphine In toluene at 95℃; for 15h; Inert atmosphere;
  • 40
  • [ 15052-09-2 ]
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  • 42
  • [ 116-14-3 ]
  • [ 627906-96-1 ]
  • (E)-2,2'-(perfluorobut-1-ene-1,4-diyl)dinaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70%Spectr. General procedure: The reactions were conducted with a pressure-tight NMR tube (Wilmad-LabGlass, 524-PV-7). To a solution of CuOtBu (2.7 mg, 0.02 mmol) and ligand in THF/THF-d8 (v/v’ = 4/1) (0.5 mL) was added arylboronic acids (0.022 mmol, 1.1 eq) and α,α,α-trifluorotoluene (2.4 L, 0.02 mmol; as an internal standard for 19F NMR). The resultant solution was transferred into the tube, and then TFE (3.5 atm, excess) was pressurized. After the reaction mixture was heated at 40 C for 24 h, Lewis acid (0.04 mmol, 2.0 eq) was added. Monitoring the reaction was performed by means of 19F NMR spectroscopy. The yields were determined by 19F NMR spectroscopy using α,α,α-trifluorotoluene as an internal standard.
  • 43
  • [ 116-14-3 ]
  • [ 627906-96-1 ]
  • (E)-2,2'-(perfluorobut-1-ene-1,4-diyl)dinaphthalene [ No CAS ]
  • 2-(1,2,2-trifluoroethenyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
5%Spectr.; 46%Spectr. General procedure: The reactions were conducted with a pressure-tight NMR tube (Wilmad-LabGlass, 524-PV-7). To a solution of CuOtBu (2.7 mg, 0.02 mmol) and ligand in THF/THF-d8 (v/v’ = 4/1) (0.5 mL) was added arylboronic acids (0.022 mmol, 1.1 eq) and α,α,α-trifluorotoluene (2.4 L, 0.02 mmol; as an internal standard for 19F NMR). The resultant solution was transferred into the tube, and then TFE (3.5 atm, excess) was pressurized. After the reaction mixture was heated at 40 C for 24 h, Lewis acid (0.04 mmol, 2.0 eq) was added. Monitoring the reaction was performed by means of 19F NMR spectroscopy. The yields were determined by 19F NMR spectroscopy using α,α,α-trifluorotoluene as an internal standard.
  • 44
  • N,N-dimethyl-2-methoxy-1-naphthamide [ No CAS ]
  • [ 627906-96-1 ]
  • [ 1415046-04-6 ]
  • 45
  • [ 404574-87-4 ]
  • [ 627906-96-1 ]
  • [ 1228658-04-5 ]
  • 46
  • [ 870-50-8 ]
  • [ 627906-96-1 ]
  • [ 868394-40-5 ]
YieldReaction ConditionsOperation in experiment
84% With water; copper diacetate; lithium tert-butoxide; In 1,2-dimethoxyethane; at 20℃;Inert atmosphere; General procedure: To a 10-mL, two-necked flask (flask A) were added Cu(OAc)2 (4.5 mg, 0.025 mmol) and LiOt-Bu (60.0 mg, 0.75 mmol), and the atmosphere inside the flask was replaced with N2 by flushing (3 ×). To the flask, DME (0.5 mL) and H2O (4.5 muL, 0.025 mmol) were added and the mixture was stirred for over 15 min. To another 10-mL two-necked flask (flask B), arylboronic ester 1 (0.25 mmol) and di-tert-butyl azodicarboxylate (2, 115.1 mg, 0.5 mmol) were added, and after flushing the atmosphere in the flask with N2 (3 ×), DME (0.5 mL) was added. The solution in flask B was added to flask A via syringe within 1 min. Flask B was rinsed with DME (0.2 mL) and the solution was added to the flask A. After stirring for 13.5-16 h at r.t., the reaction was diluted with EtOAc (4 mL) and H2O (2-3 mL) and quenched with 1 M citric acid to neutralize the system. The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel) to provide the hydrazine. Di-tert-butyl 1-(Naphthalen-2-yl)hydrazine-1,2-dicarboxylate (3j) [5,14]. White solid; yield: 75.4 mg (84%); Rf = 0.31 (hexane-EtOAc, 5:1). 1H NMR (400 MHz, CDCl3): delta = 1.50, 1.52 (overlapped s, 18 H), [6.74, 6.94 (br s, 1 H)], 7.40-7.44 (m, 2 H), 7.57 (d, J = 8.4 Hz, 1 H), 7.76-7.78 (m, 3 H), 7.86 (s, 1 H). 13C NMR (100 MHz, CDCl3): delta = 28.3, 81.8, 82.5, 121.5, 123.1, 125.7, 126.3, 127.6, 128.0, 128.2, 131.5, 133.4, 139.7, 153.8, 155.6.
  • 47
  • [ 93-04-9 ]
  • [ 201733-56-4 ]
  • [ 612-78-2 ]
  • [ 627906-96-1 ]
  • 48
  • [ 17763-67-6 ]
  • [ 917-57-7 ]
  • [ 627906-96-1 ]
  • (R)-1-(naphthalen-2-yl)-2-phenylethan-1-ol [ No CAS ]
  • 49
  • tert-butyl (2-naphthoyl)(methyl)carbamate [ No CAS ]
  • [ 201733-56-4 ]
  • [ 627906-96-1 ]
  • 50
  • [ 53040-92-9 ]
  • [ 627906-96-1 ]
  • 2-(4'-methyl-[1,1'-biphenyl]-4-yl)naphthalene [ No CAS ]
  • 51
  • [ 34143-82-3 ]
  • [ 627906-96-1 ]
  • C24H19N [ No CAS ]
  • 52
  • [ 201230-82-2 ]
  • [ 2643-22-3 ]
  • [ 627906-96-1 ]
  • N,N-diethyl-2,2-difluoro-3-(naphthalen-2-yl)-3-oxopropanamide [ No CAS ]
  • 53
  • [ 82408-29-5 ]
  • [ 201733-56-4 ]
  • [ 627906-96-1 ]
  • 54
  • [ 2040-04-2 ]
  • [ 627906-96-1 ]
  • 1-(2-methoxy-6-(naphthalen-2-yl)phenyl)ethan-1-one [ No CAS ]
  • 55
  • [ 447-60-9 ]
  • [ 627906-96-1 ]
  • 6-(2-naphthyl)-2-(trifluoromethyl)benzonitrile [ No CAS ]
  • 56
  • [ 5145-65-3 ]
  • [ 627906-96-1 ]
  • [ 644-13-3 ]
  • 57
  • [ 898766-24-0 ]
  • [ 627906-96-1 ]
  • 3,5-dimethyl-2-(2-naphthyl)pivalophenone [ No CAS ]
  • 58
  • [ 412284-19-6 ]
  • [ 201733-56-4 ]
  • [ 627906-96-1 ]
  • 59
  • [ 6364-05-2 ]
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  • 60
  • [ 7508-21-6 ]
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  • [ 57537-02-7 ]
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  • 63
  • [ 627906-96-1 ]
  • [ 142-30-3 ]
  • 2,5-dimethyl-3-(naphthalen-2-yl)hexa-3,4-dien-2-ol [ No CAS ]
  • 64
  • C13H20O2 [ No CAS ]
  • [ 627906-96-1 ]
  • (2S,6S,E)-1-methoxy-5-methyl-7-(naphthalen-2-yl)undeca-3,5,6-trien-2-ol [ No CAS ]
  • (2R,6S,E)-1-methoxy-5-methyl-7-(naphthalen-2-yl)undeca-3,5,6-trien-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-ethyl-N,N-diisopropylamine; bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; water; at 25℃; for 2h;Inert atmosphere; Schlenk technique; General procedure: A palladium complex, ligand, and the dry THF (half of the volume necessary for the reaction) were added successively into a Schlenk apparatus that is attached to an Ar line and stirred 15 minat 25 C. Then, the dry THF (remaining half volume) solution of organoboron, enyne oxirane (1), and degassed water were added successively. The mixture was stirred magnetically in a preheated water or an oil bath. When the reaction was complete, as judged by TLC analysis, the solvent was evaporated under reduced atmosphere and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate), affording the product 3 as colourless oil unless otherwise mentioned. In the case of optimization studies, the reaction mixture was filtered through a short silica gel column, washed with Et2O, dried with MgSO4 and evaporated under reduced atmosphere. The residue was analysed by 1H NMR using p-anisaldehyde as the internal standard. Aldehyde and methoxy hydrogen signals were used in the quantitative analyses.
  • 65
  • C20H30N2O2Si [ No CAS ]
  • [ 627906-96-1 ]
  • (E)-4-(((5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(naphthalen-2-yl)furan-2-yl)methylene)amino)-N,N-dimethylaniline [ No CAS ]
  • 66
  • [ 13546-87-7 ]
  • [ 627906-96-1 ]
  • (E)-N,N-dimethyl-4-(((3-(naphthalen-2-yl)furan-2-yl)methylene)amino)aniline [ No CAS ]
  • 67
  • (E)-4-((5-methylfuran-2-ylmethylene)amino)-N,N-dimethylaniline [ No CAS ]
  • [ 627906-96-1 ]
  • (E)-N,N-dimethyl-4-(((5-methyl-3-(naphthalen-2-yl)furan-2-yl)methylene)amino)aniline [ No CAS ]
  • 68
  • [ 5765-65-1 ]
  • [ 1440956-86-4 ]
  • [ 627906-96-1 ]
  • 4-((1S*,2R*,3S*)-2-(4-bromophenyl)-2-methyl-3-(naphthalen-2-yl)cyclopropyl)morpholine [ No CAS ]
  • 4-(2-(4-bromophenyl)-2-methyl-3-(naphthalen-2-yl)cyclopropyl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Add tetrahydrofuran as a solvent (2 ml) in a 25 ml reaction tube.Adding cuprous chloride (0.010 mmol) in turn,Dppbz L1 (5.4 mg, 0.06 mmol),Stir at room temperature for 2 min; add m-CPBA (2 mg, 0.01 mmol),Sodium tert-butoxide (28.8 mg, 0.3 mmol) was stirred for 2 min;Then the substrate molar mass of 1.2 times the amount of 2-naphthalene borate neopentyl glycol ester (57.6 mg, 0.24 mmol), stirred for about 2 min;Add 3-methyl-3-(4-bromophenyl)cyclopropene (0.2 mmol),The reaction system of benzoyloxymorpholine (50 mg, 0.24 mmol) was stirred at room temperature.TLC point plate monitoring, after the reaction is complete,Separation and purification by column chromatography gave an oily liquid which was subjected to 1H NMR (as shown in Fig. 9) and 13C NMR (as shown in Fig. 10).The structure was determined to be Formula 5, the weighing weight was 62 mg, the calculated yield was 73%, and dr = 89:11;
  • 69
  • [ 65051-83-4 ]
  • o-benzoyl-N-benzyl-N-(pent-4-en-1-yl)hydroxylamine [ No CAS ]
  • [ 627906-96-1 ]
  • C31H31N [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Add tetrahydrofuran as a solvent (2 ml) in a 25 ml reaction tube.Adding cuprous chloride (0.010 mol),Dppbz L1 (5.4 mg, 0.06 mmol),Stir at room temperature for 2 min; add m-CPBA (2 mg, 0.01 mmol),Sodium tert-butoxide (28.8 mg, 0.3 mmol) was stirred for 2 min;Then the substrate molar mass of 1.2 times the amount of 2-naphthylboronic acid neopentyl glycol ester (57.3 mg, 0.24 mmol), stirred for about 2 min;3-methyl-3-phenylcyclopropene (0.2 mmol) was added,The reaction system of O-benzoyl-N-benzyl-N-(pent-4-en-1-yl)hydroxylamine (74 mg, 0.24 mmol) was stirred at room temperature.TLC point plate monitoring, after the reaction is completed, it is separated and purified by column chromatography.Obtaining an oily liquid which was subjected to 1H NMR (as shown in Figure 17),13C NMR (as shown in Figure 18), the structure is determined to be Equation 9,The weighing weight was 53.2 mg, and the calculated yield was 66%.Dr>98:2;
  • 70
  • [ 5765-65-1 ]
  • [ 65051-83-4 ]
  • [ 627906-96-1 ]
  • 4-((1S*,2R*,3S*)-2-methyl-3-(naphthalen-2-yl)-2-phenylcyclopropyl)morpholine [ No CAS ]
  • 4-(2-methyl-3-(naphthalen-2-yl)-2-phenylcyclopropyl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Add tetrahydrofuran as a solvent (2 ml) in a 25 ml reaction tube, and sequentially add cuprous chloride (0.010 mmol),Dppbz L1 (5.4 mg, 0.06 mmol),Stir at room temperature for 2 min; add m-CPBA (2 mg, 0.01 mmol),Sodium tert-butoxide (28.8 mg, 0.3 mmol) was stirred for 2 min;Then the substrate molar mass of 1.2 times the amount of 2-naphthalene borate neopentyl glycol ester (57.6 mg, 0.24 mmol), stirred for about 2 min;3-methyl-3-phenylcyclopropene (0.2 mmol) was added,The reaction system of benzoyloxymorpholine (50 mg, 0.24 mmol) was stirred at room temperature.TLC point plate monitoring, after the reaction is completed, it is separated and purified by column chromatography.Obtaining an oily liquid which was subjected to 1H NMR (Fig. 1),13C NMR (shown in Figure 2), the structure is determined to be Equation 1,Weighing weight is 68 mg, calculated yield is 99%,dr93:7
  • 71
  • [ 5765-65-1 ]
  • 1-chloro-3-(1-methylcycloprop-2-en-1-yl)benzene [ No CAS ]
  • [ 627906-96-1 ]
  • 4-((1S*,2R*,3S*)-2-(3-chlorophenyl)-2-methyl-3-(naphthalen-2-yl)cyclopropyl)morpholine [ No CAS ]
  • 4-(2-(3-chlorophenyl)-2-methyl-3-(naphthalen-2-yl)cyclopropyl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Tetrahydrofuran was added as a solvent (2 ml) to a 25 ml reaction tube, followed by the addition of cuprous chloride (0.010 mmol), dppbz L1 (5.4 mg, 0.06 mmol).Stir at room temperature for 2 min; add m-CPBA (2 mg, 0.01 mmol),Sodium tert-butoxide (28.8 mg, 0.3 mmol) was stirred for 2 min;Then the substrate molar mass of 1.2 times the amount of 2-naphthalene borate neopentyl glycol ester (57.6 mg, 0.24 mmol), stirred for about 2 min;3-methyl-3-(3-bromophenyl)cyclopropene (0.2 mmol) was added,The reaction system of benzoyloxymorpholine (50 mg, 0.24 mmol) was stirred at room temperature.TLC point plate monitoring, after the reaction is complete,Separated and purified by column chromatography to give a yellow solid.The solid was subjected to 1H NMR (as shown in Figure 11),13C NMR (as shown in Figure 12),The structure was determined to be Equation 6, the weighing weight was 43.1 mg, and the calculated yield was 57%.Dr=83:17;
  • 72
  • [ 5765-65-1 ]
  • 1-methoxy-3-(1-methylcycloprop-2-en-1-yl)benzene [ No CAS ]
  • [ 627906-96-1 ]
  • 4-((1S*,2R*,3S*)-2-(3-methoxyphenyl)-2-methyl-3-(naphthalen-2-yl)cyclopropyl)morpholine [ No CAS ]
  • 4-(2-(3-methoxyphenyl)-2-methyl-3-(naphthalen-2-yl)cyclopropyl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Add tetrahydrofuran as a solvent (2 ml) in a 25 ml reaction tube.Adding cuprous chloride (0.010 mmol), dppbz L1 (5.4 mg, 0.06 mmol), and stirring at room temperature for 2 min;Add m-CPBA (2 mg, 0.01 mmol),Sodium tert-butoxide (28.8 mg, 0.3 mmol) was stirred for 2 min;Then the substrate molar mass of 1.2 times the amount of 2-naphthalene borate neopentyl glycol ester (57.6 mg, 0.24 mmol), stirred for about 2 min;3-methyl-3-(3-methoxyphenyl)cyclopropene (0.2 mmol) was added,The reaction system of benzoyloxymorpholine (50 mg, 0.24 mmol) was stirred at room temperature.TLC point plate monitoring, after the reaction is completed, it is separated and purified by column chromatography.Obtained as a white solid which was subjected to 1H NMR (as shown in Figure 13).13C NMR (shown in Figure 14), the structure is determined to be Equation 7,Weighing weight is 40.3 mg, calculated yield is 54%, dr = 91:9;
  • 73
  • [ 930-22-3 ]
  • [ 627906-96-1 ]
  • (E)-4-(naphthalen-2-yl)but-3-en-1-ol [ No CAS ]
  • 74
  • [ 930-22-3 ]
  • [ 141-78-6 ]
  • [ 627906-96-1 ]
  • C16H16O2 [ No CAS ]
  • 75
  • [ 10075-72-6 ]
  • [ 627906-96-1 ]
  • 8-(methylsulfanyl)-1,2'-binaphthalene [ No CAS ]
  • 76
  • [ 591-50-4 ]
  • N-(2,4-dimethoxybenzyl)but-3-enamide [ No CAS ]
  • [ 627906-96-1 ]
  • N-(2,4-dimethoxybenzyl)-3-(naphthalen-2-yl)-4-phenylbutanamide [ No CAS ]
  • 77
  • [ 75456-63-2 ]
  • [ 627906-96-1 ]
  • (E)-2-(undec-1-enyl)naphthalene [ No CAS ]
  • 78
  • [ 35466-83-2 ]
  • [ 2700-22-3 ]
  • [ 627906-96-1 ]
  • 2-allyl-2-(naphthyl(phenyl)methyl)malononitrile [ No CAS ]
  • 79
  • C16H18N2 [ No CAS ]
  • [ 627906-96-1 ]
  • [ 1183936-56-2 ]
  • 80
  • C16H18N2 [ No CAS ]
  • [ 627906-96-1 ]
  • C24H19N [ No CAS ]
  • 81
  • [ 5765-65-1 ]
  • [ 1064001-49-5 ]
  • [ 627906-96-1 ]
  • 4-(2-methyl-3-(naphthalen-2-yl)-2-(4-(trifluoromethyl)phenyl)cyclopro-pyl)morpholine [ No CAS ]
  • 4-((1S*,2R*,3S*)-2-methyl-3-(naphthalen-2-yl)-2-(4-(trifluoromethyl)phenyl)cyclopropyl)morpholine [ No CAS ]
  • 82
  • [ 5765-65-1 ]
  • [ 1256842-24-6 ]
  • [ 627906-96-1 ]
  • 4-((1R*,2S*,3S*)-2-(naphthalen-2-yl)-3',4'-dihydro-2'H-spiro[cyclopropane-1,1'-naphthalen]-3-yl)morpholine [ No CAS ]
  • 83
  • [ 5765-65-1 ]
  • [ 22825-21-4 ]
  • [ 627906-96-1 ]
  • 4-((1S*,3S*)-3-(naphthalen-2-yl)-2,2-diphenylcyclopropyl)morpholine [ No CAS ]
  • 84
  • [ 5765-65-1 ]
  • (2-(1-methylcycloprop-2-en-1-yl)ethyl)benzene [ No CAS ]
  • [ 627906-96-1 ]
  • 4-(2-benzyl-2-methyl-3-(naphthalen-2-yl)cyclopropyl)morpholine [ No CAS ]
  • 85
  • [ 92197-18-7 ]
  • [ 65051-83-4 ]
  • [ 627906-96-1 ]
  • (1S*,2R*,3S*)-N,N-diisopropyl-2-methyl-3-(naphthalen-2-yl)-2-phenylcyclopropan-1-amine [ No CAS ]
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