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Structure of 119-64-2 * Storage: {[proInfo.prStorage]}
* 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.
Reference：
[1] Bulletin de la Societe Chimique de France, 1970, p. 2001 - 2004
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 2597,2600
14
[ 119-64-2 ]
[ 27969-97-7 ]
[ 13577-40-7 ]
Reference：
[1] Journal of Organometallic Chemistry, 1988, vol. 342, p. 315 - 338
15
[ 119-64-2 ]
[ 108-24-7 ]
[ 774-55-0 ]
[ 13577-40-7 ]
Reference：
[1] Patent: US2588123, 1946, ,
16
[ 119-64-2 ]
[ 19353-86-7 ]
[ 29809-14-1 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1922, vol. 426, p. 132
[2] Journal of the Chemical Society, 1931, p. 3176,3178
[3] Justus Liebigs Annalen der Chemie, 1922, vol. 426, p. 132
[4] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 322 - 331
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 387 - 391
[6] Patent: US2012/178748, 2012, A1, . Location in patent: Page/Page column 51
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 317
[8] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 317
17
[ 74-83-9 ]
[ 119-64-2 ]
[ 1680-51-9 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1930, vol. <4> 47, p. 1314,1318
18
[ 119-64-2 ]
[ 1680-51-9 ]
Reference：
[1] Sci. Tokyo, 1947, vol. 17, p. 370[2] Chem.Abstr., 1951, p. 1989
With acetic acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water
EXAMPLE II-18 (Synthesis of Ex. Comp. No. (II-15)) In a 5 liter-three necked flask, 169.5 g (1.28 M) of 1,2,3,4-tetrahydronaphthalene and 3 liters of acetic acid were placed and stirred at room temperature. Under stirring, to the mixture, 650 g (1.67 M) of benzyltrimethylammonium bromide and 244.8 g (1.80 M) of zinc chloride were successively added, followed by stirring for 5.5 hours at 70° C. After the reaction, the reaction mixture was cooled to room temperature and poured into 3 liters of ice water, followed by extraction with methyl t-butyl ether. The organic layer was successively washed with 5percent-NaHSO3 aqueous solution, 5percent-NaOH aqueous solution and distilled water, followed by distilling-off of the solvent under reduced pressure to obtain 243.2 g of a dark brown liquid. The liquid was subjected to vacuum distillation (distillation under reduced pressure) (boiling point=108-110° C. at 667 Pa) to obtain 130.2 g of 6-bromo-1,2,3,4-tetrahydronaphthalene (Yield: 48.1percent).
Reference：
[1] Patent: US2002/64681, 2002, A1,
21
[ 119-64-2 ]
[ 6134-56-1 ]
Yield
Reaction Conditions
Operation in experiment
42%
for 0.166667 h;
Step 1 : 2-Bromo-5,6,7,8-tetrahydronaphthaleneTo aluminum oxide (neutral Brockman grade 1) (8 g) was added 1,2,3,4- tetrahydronaphthalene (1.06g, 8mmol). The mixture was stirred to give a homogeneous mixture. To this mixture was added over 5 minutes a mixture of bromine (1.44g, 9mmol) on alumina (8g). After stirring for another 5 minutes the mixture was added to a plug of silica gel was washed with methylene chloride (200ml). The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using 100percent heptane to give the title compound containing some starting material (0.65g, 42percent).
Reference：
[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
[2] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 42
22
[ 119-64-2 ]
[ 6134-55-0 ]
[ 6134-56-1 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1983, vol. 2, # 3-4, p. 96 - 104
[2] Patent: WO2004/792, 2003, A1, . Location in patent: Page 21
23
[ 119-64-2 ]
[ 638-29-9 ]
[ 101498-55-9 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6749 - 6753
[2] Doklady Chemistry, 1960, vol. 131, p. 251 - 253[3] Doklady Akademii Nauk SSSR, 1960, vol. 131, # 2, p. 335 - 337
[4] Brennstoff-Chemie, 1949, vol. 30, p. 73,75
[5] Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 792,798[6] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1958, vol. <B> 61, p. 103,105
With aluminum (III) chloride; In dichloromethane; at 20℃;Inert atmosphere;
General procedure: AlCl3 (1.0 g, 7.5 mmol)was added portion-wise to a solution of succinic anhydride (0.5 g, 5 mmol) and anaromatic compound (6 mmol) in CH2Cl2 (5 mL) at room temperature. The mixture wasstirred at room temperature for overnight, and the mixture was poured into 1N HClsolution (10 mL), extracted with ethyl acetate (15 mL x 3). The organic layer was driedover MgSO4. The solvent was removed under reduced pressure, and the crude productwas purified by recrystallized from ethyl acetate and hexane.
68%
With aluminum tri-bromide; In benzene;Inert atmosphere; Reflux;
Tetraline (5 g, 37.8 mmol) was dissolved in dry benzene (30 mL) and succinanhydride (2.5 g, 25 mmol) was added. Under dry and inert atmosphere (N2), AlBr3 (14 g, 52 mmol) was added portionwise. After the addition of entire quantity of AlBr3, the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to rt and poured over finely chrushed ice. The product was isolated by extraction with Et2O (3×30 mL). The combined organic extracts were dryed over anhydrous MgSO4, filtered and the solvent was removed on a rotary evaporator. The crude product was recrystallized from toluene to afford the pure product 12 (6 g, 68%) in the form of colorless solid.
With copper(II) nitrate trihydrate; acetic anhydride; In diethyl ether; at 20℃; for 16.0h;
a. 6-Nitro-1,2,3,4-tetrahydronaphthalene and 5-nitro-1,2,3,4-tetrahydronaphthaleneTo a solution of 1,2,3,4-tetrahydronaphthalene (26.4 g, 200 mmol) in Et2O (200 mL) was added acetic anhydride (67 mL, 760 mmol) and cupric nitrate trihydrate (48.4 g, 200 mmol). The resulting mixture was stirred at room temperature for 16 h. After filtration, the filtrate was concentrated, and the residue was purified by silica gel column (PE/EtOAc v/v 100:2) to give a yellow oil (5.5 g, yield 15.6%) as a mixture of 6-nitro-1,2,3,4-tetrahydro-naphthalene and 5-nitro-1,2,3,4-tetrahydronaphthalene, which was used in the next step. ESI MS: m/z 178 [M+H]+.
With N-Bromosuccinimide; In tetrachloromethane; at 100℃; for 12h;Inert atmosphere;
Under the protection of nitrogen, 4H-naphthalene 1n (0.5 mmol), NBS (2.0 mmol) and carbon tetrachloride (5 mL) were added to the reaction tube. Stir at 100 C for 12 hours. After stopping the reaction, cool to room temperature, evaporate the solvent and separate by column chromatography. The volume ratio (mL / mL) of the eluent used is ethyl acetate: petroleum ether = 0: 100 ~ 1: 200. Bromine-4H-naphthalene 3n, the yield is 60%, and the ratio of diastereomers is: trans: cis> 95: 5.
With chlorotriisopropylsilane; diphenyl(pentafluorophenyl)phosphonium tetrakis(perfluorophenyl)borate; In dichloromethane; at 50℃; for 18h;Inert atmosphere; Schlenk technique;
General procedure: A reaction tube with a Teflon cap was charged with equimolar(0.1 mmol) amounts of olefin and triisopropylsilane. Adichloromethane solution of 10 mol% catalyst was added to the tube and the mixture was heated at 50 C for 18 h. The reactionmixture was taken in volumetric flask and diluted with DCM. Thediluted solution was analysed by GC-MS.
a) Preparation of '5,6, 7, 8-tetrahydronaphthalene-2-carbaldehyde 1,2,3,4-tetrahydronaphthalene (14.5g; 110 mmol) was dissolved in dry of CH2CI2 (100 ml) and the solution cooled to 0 C on an ice bath. With vigorous stirring, SnCl4 (33.4 g; 164 mmol) was add all at once via syringe, followed by the dropwise introduction of dichloromethyl methyl ether (12.6 g; 110 mmol) over a 20 minutes period. After 20 more minutes the ice bath was removed, and the dark mixture was quenched by the addition of 100 ml of ice-water. The reaction was extracted with diethyl ether (2 x 250 ml). Each extract was washed with water (2 x 100 ml), 5 % aqueous HC1 (50 ml) and brine (2 x 100 ml). Combined extracts were dried over sodium sulfate. The product was purified by column chromatography on silica gel (heptane/ethyl acetate 98:2) followed by bulb-to-bulb distillation (85 C/0.002 mbar). The product was obtained as a liquid (40.5 mmol; yield: 44%) 13C-NMR (major isomer): 192.28 (d); 144.86 (s); 138.01 (s); 134.24 (s); 130.80 (d); 129.81 (d); 126.59 (d); 29.93 (t); 29.23 (t); 22.84 (t); 22.72 (t). ^-NMR: 9.91 (s, 1 H); 7.60-7.50 (m, 2 H); 7.19 (d, J = 7.5 Hz, 1 H); 2.82 (m, 4 H); 1.81 (m, 4 H).
Bromine (66.1 g, 0. [41] mol) ) was added over 3 hours, with stirring at [5 C] to 10 [C,] to the 1,2, 3,4-tetrahydronaphthalene (50 g, 0.374 mol) along with a small piece of iodine (0.25 g, 0.98 mmol). Stirring was continued at ambient temperature for 6 hours and the mixture was then poured slowly into a stirred saturated aqueous solution of sodium sulphite (200 ml) at [10 C.] Stirring was continued for 15 minutes, the resulting mixture was extracted with methylene chloride (3 x 50 [ML),] the combined organic extracts were washed with water (200 ml), dried [(MGS04)] and solvent removed by evaporation in vacuo to give 5- [BROMO-1,] 2,3, 4-tetrahydronaphthalene along with the [6-BROM-1,] 2,3, 4- tetrahydronaphthalenec isomer (86 g, 89.7% purity of combined mono-brominated isomers present in circa 3: 2 ratio, combined mono-bromo isomer yield 96%).
With dimethylsulfoxide-d6; potassium tert-butylate; at 80℃; for 1h;Inert atmosphere;
General procedure: To a solution of KOt-Bu (11.3 mg, 0.1 mmol) in DMSO-d6 (1.5 mL) was added N,N-dimethyl-1-phenylmethanamine (135.0 mg,1.0 mmol). The reaction mixture was then stirred at 80 C under argon atmosphere for 1.0 h. After being cooled to room temperature,the reaction mixture was poured into water (10 mL), and followed by the extraction with ethyl acetate (15 mL3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under vacuum. The residue was purified by flash column chromatography over silica gel to give 2a as a colorless oil (119.0 mg, 87% yield).
With tert.-butylhydroperoxide; 2.9-dimethyl-1,10-phenanthroline; copper(II) choride dihydrate; In water; at 20℃; for 1h;
General procedure: A stock solution of CuCl2·2H2O in water (0.0171 g/mL) was prepared (by dissolving 0.171 g in 10 mL H2O). To a Teflon screw cap glass tube, catalyst A (100 muL of a stock solution, 0.01 mmol of CuCl2, 2.1mg, 0.01 mmol of neocuproine) was added. Then 0.7 mL of H2O, 0.2 mmol of arylalkanes, and 70 % aq tert-butyl hydroperoxide (200 muL, 1.4 mmol) were added in each case. The mixture was stirred vigorously at room temperature till to its reaction time specified in the Tables 2 and 3. The reaction mixture was then diluted with ethyl acetate and the products dissolved in ethyl acetate layer were analyzed by GC using internal standard 1,4-di-tert-butylbenzene (19.4 mg, 0.1 mol). For product separation, the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined extracts were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated and product isolation was carried out by TLC. The pure products of benzophenone, 9-fluorenone (Table 2, entries 2 and 3) and 4-methoxyacetophenone (Table 3 entry 2) were obtained from drying their ethyl acetate extract without chromatographic workup. Filtration of the reaction mixture afforded pure 9-xanthenone (Table 2, entry 4).
With triethylsilane; indium(III) bromide; In chloroform; at 60℃; for 1h;Inert atmosphere;
General procedure: To a freshly distilled CHCl3 solution (0.6 mL) in a screw-capped vial under N2 atmosphere, InBr3 (10.6 mg, 0.0300 mmol), aromatic ketone 4 (0.6 mmol) and Et3SiH (383 muL, 2.40 mmol) was successively added. The resulting mixture was stirred at 60 C (bath temperature) or room temperature, and monitored by TLC or GC analysis until consumption of the starting ketone. The reaction was quenched with H2O. The aqueous layer was extracted with CH2Cl2 (5 mL × 3), the organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by a silica gel column chromatography (hexane/AcOEt = 19/1) to give the corresponding alkylbenzene 5. 1-Cyano-4-[1-(triethylsiloxy)ethyl]benzene (5k): 85% yield; colorless oil; 1H NMR (500 MHz, CDCl3) delta 0.54-0.62 (m, 6H), 0.90-0.93 (m, 9H), 1.41 (d, 3H, J = 6 Hz), 4.90 (q, 1H, J = 6 Hz), 7.45 (d, 2H, J = 8 Hz), 7.61 (d, 2H, J = 8 Hz); 13C NMR (125 MHz, CDCl3) delta 4.7, 6.7, 27.0, 69.9, 110.5, 119.0, 125.8, 132.0, 152.3; MS (ESI): m/z 284 (M++Na); HRMS (ESI): Calcd for C15H23NNaOSi: 284.1447, Found: 284.1407.
With aluminum (III) chloride; In dichloromethane; at -15 - 20℃;Inert atmosphere;
A suspension of aluminium chloride (5.58 g, 0.042 mol) in DCM (30 ml) under an argon atmosphere was cooled to -10C with vigorous stirring. To this was added dropwise a solution of 3-chloropropionyl chloride (3.6 ml, 0.038 mol) and <strong>[119-64-2]tetralin</strong> (5 g, 0.038 mol) in DCM (10 ml) over 0.5 h, the temperature was kept between -15C and -5C. The reaction was allowed to warm to rt and stirred overnight. The reaction mixture was added dropwise to cold (0C) 2 M HCI over 30 min with the temperature kept between 0C and 10C. The layers were separated and the aqueous phase washed with DCM (3 x 20 ml). The combined organic layers were washed sequentially with water, saturated sodium bicarbonate and brine. The organic phases were dried over Na2SO4, filtered and evaporated under reduced pressure to provide 3-chloro-l-(2,3-dihydro-lH-inden-5-yl)propan-l-one as a yellow solid.Y = 91%MS ES+: not ionised1H NMR (400 MHz, DMSO-d6) delta 7.84 (d, 1H), 7.69 - 7.66 (m, 2H), 7.20 (d, J = 8 Hz, 1H), 3.91 (t, J = 6 Hz, 2H), 3.49 (t, J = 6 Hz, 2H), 2.78 (d, J = 4 Hz, 4H), 1.77 - 1.72 (m, 4H).
Step 1 : 2-Bromo-5,6,7,8-tetrahydronaphthaleneTo aluminum oxide (neutral Brockman grade 1) (8 g) was added 1,2,3,4- tetrahydronaphthalene (1.06g, 8mmol). The mixture was stirred to give a homogeneous mixture. To this mixture was added over 5 minutes a mixture of bromine (1.44g, 9mmol) on alumina (8g). After stirring for another 5 minutes the mixture was added to a plug of silica gel was washed with methylene chloride (200ml). The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using 100% heptane to give the title compound containing some starting material (0.65g, 42%).
With acetic acid;Zinc chloride; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water;
EXAMPLE II-18 (Synthesis of Ex. Comp. No. (II-15)) In a 5 liter-three necked flask, 169.5 g (1.28 M) of 1,2,3,4-tetrahydronaphthalene and 3 liters of acetic acid were placed and stirred at room temperature. Under stirring, to the mixture, 650 g (1.67 M) of benzyltrimethylammonium bromide and 244.8 g (1.80 M) of zinc chloride were successively added, followed by stirring for 5.5 hours at 70° C. After the reaction, the reaction mixture was cooled to room temperature and poured into 3 liters of ice water, followed by extraction with methyl t-butyl ether. The organic layer was successively washed with 5percent-NaHSO3 aqueous solution, 5percent-NaOH aqueous solution and distilled water, followed by distilling-off of the solvent under reduced pressure to obtain 243.2 g of a dark brown liquid. The liquid was subjected to vacuum distillation (distillation under reduced pressure) (boiling point=108-110° C. at 667 Pa) to obtain 130.2 g of 6-bromo-1,2,3,4-tetrahydronaphthalene (Yield: 48.1percent).
With tert.-butylnitrite; N-hydroxyphthalimide; In acetonitrile; at 90℃; for 36h;Schlenk technique;
To the 25 mL Schlenk reaction tube was added NHPI 1.0 equiv., Vacuum dried for 15 min, oxygen balloon was added, followed by addition of acetonitrile lmL, t-butyl nitrite 2.0 equivalents, 1,2,3,4-tetrahydronaphthalene 0.5mmol, in the reaction tube with poly tetrafluoro plug after the oil into the pot, 90 C reaction 36h. After completion of the reaction, the solvent acetonitrile was concentrated under reduced pressure, and the eluent was petroleum ether / ethyl acetate (nu: 10: 1) to give 2,3-dihydro-1,4-naphthoquinone The The product yield was 72%, gray solid
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In decane; benzene; at 20 - 90℃; for 12h;Schlenk technique;
General procedure: An over-dried Schlenk tube was charged with tetrabutylammonium iodide (TBAI) (0.1 mmol),phenylglyoxylic acid (1a) (0.5 mmol) and cyclohexene (2a) (1.5 mmol) in benzene (2 mL) wasadded, Then tert-butyl hydroperoxide (1.25 mmol, 5~6 M in decane) was added dropwise into themixture at room temperature. The resulting mixture was stirred at 90 C for 12 h. Then, the cooledreaction mixture was dissolved in water (5 mL) and extracted with CH2Cl2 (3×5 mL). Thecombined organic layer was dried with anhydrous MgSO4, and the product was further purified bysilica gel column chromatography and eluted with ethyl acetate and petroleum ether mixture toafford the product.
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