Structure of 31729-66-5
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CAS No. : | 31729-66-5 |
Formula : | C10H12O |
M.W : | 148.20 |
SMILES Code : | OCC1(C2=CC=CC=C2)CC1 |
MDL No. : | MFCD00001310 |
InChI Key : | APALRPYIDIBHQN-UHFFFAOYSA-N |
Pubchem ID : | 520536 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[673] Example 173 - 3-ri-Methyl-5-(4-methyl-cyclohexyl)-l,2,3,6-tetrahydro-pyridin-4-yl1-5-(l-; [674] To a solution of 1 -phenyl- 1-cyclopropanecarboxylic acid (1.18 g, 5.0 mmol) in anhydrous ether (10 mL) at 0 C was added slowly lithium aluminum hydride solution in THF (1.0 M, 6.0 mL)). The reaction was then stirred at RT for 2 hr. To the reaction mixture was then added water (0.24 mL), 15% aqueous NaOH (0.24 mL), and water (0.72 mL) while stirring. The mixture was stirred for 20 min at RT, filtered and concentrated to give the crude 173A, which was used for the next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Dess-Martin periodane; In dichloromethane; for 24h; | EXAMPLE 7C A solution of EXAMPLE 7B (1.14 g) and Dess-Martin reagent (3.4 g) in dichloromethane (25 mL) was stirred for 24 hours, filtered and concentrated. The concentrate was flash chromatographed on silica gel with 10% ethyl acetete/hexanes. | |
With pyridinium chlorochromate; In dichloromethane; at 20℃; for 12h;Molecular sieve; | [675] To a suspension of 173A and molecular sieves (powdered, activated, 4A) in DCM was added PCC (10 mmol). After stirring for 12 hr at RT, the reaction was filtered through silica gel, and concentrated to give crude aldehyde 173B, which was used for the next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine; In ice-water; dichloromethane; | 1.1 Preparation of 1-[benzo-1,2,3-thiadiazole-7-carbonyloxymethyl]-1-phenylcyclopropane STR20 A solution of 6.7 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 33 ml of dichloromethane is added dropwise at a maximum of 15 C., with cooling, to a solution of 5.0 g of <strong>[31729-66-5]1-phenylcyclopropanemethanol</strong>, 6.1 ml of triethylamine and 200 mg of 4-dimethylaminopyridine in 50 ml of dichloromethane. The mixture is stirred overnight at room temperature until the reaction is complete, dichloromethane and ice-water are added, the aqueous phase is extracted with dichloromethane, and the organic phase is washed with water and NaCl solution, dried over Na2 SO4 and concentrated by evaporation. The residue is purified on silica gel (hexane-ethyl acetate 1:1) and the product obtained is recrystallized from diethyl ether/hexane. 7.5 g of crystals having a melting point of 55-57 C. are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.3% | (1) Synthesis of 4-methoxy-3-[(1-phenylcyclo-propyl)methoxy]nitrobenzene According to the same procedure as in Example 9(1), using 1-phenylcyclopropylmethanol instead of 2-indanol, 4-methoxy-3-[(1-phenylcyclopropyl)methoxy]nitrobenzene (yield 69.3%) was obtained as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ 1.03-1.06 (4H, m), 3.92 (3H, s), 4.14 (2H, s), 6.86 (1H, d, J=8.79 Hz), 7.20-7.24 (1H, m), 7.29-7.32 (2H, m), 7.43-7.45 (2H, m), 7-63 (1H, d, J=2.44 Hz), 7.87 (1H, dd, J38.79, 2.44 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.8% | (1) Synthesis of 4-methoxy-3-[(1-phenylcyclopropyl)methyloxy]benzaldehyde According to the same procedure as in Example 4(1), using 1-phenylcyclopropylmethanol instead of cyclopropylcarbinol, 4-methoxy-3-[(1-phenylcyclopropyl)methyloxy]benzaldehyde (yield 74.8%) was obtained as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ1.00-1.02 (2H, m), 1.04-1.07 (2H, m), 3.90 (3H, s), 4.13 (2H, s), 6.93 (1H, d, J=7.81 Hz), 7.19-7.23 (1H, m), 7.28-7.31 (3H, m), 7.41-7.45 (3H, m), 9.79 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | EXAMPLE 70 1-[[1-[[(1-Phenyl-1-cyclopropyl)methoxy]carbonyl]-4-piperidyl]methyl]-1H-2-methylimidazo[4,5-c]pyridine Following the procedure described in example 36, but using phenyl (1-phenyl-1-cyclopropyl)methyl carbonate (prepared from <strong>[31729-66-5]1-phenyl-1-cyclopropanemethanol</strong> and phenyl chloroformate) instead of N-phenoxycarbonyl-L-Leucine ethyl ester, the title compound was obtained as a white solid (23%). mp: 138-140 C. (C24 H28 N4 O2.1/2H2 O); 1 H NMR (80 MHz, CDCl3) δ (TMS): 8.97 (s, 1H), 8.37 (d, J=5.5 Hz, 1H), 7.27 (m, 5H), 7.19 (d, J=5.5 Hz, 1H), 4.16 (s, 2H), 4.15 (broad d, J=13.6 Hz, 2H), 3.94 (d, J=7.21 Hz, 2H), 2.60 (s, 3H), 2.60 (m, 2H), 2.3-0.8 (m, 5H), 0.92 (s, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 7B A solution of EXAMPLE 7A (2.97 g) in THF (55 mL) at 0 C. was treated with 1M DIBAL in THF (39 mL) over 2 hours, quenched with water, mixed with ethyl acetate (300 mL) and water (50 mL) and filtered through silica gel. The filtrate was washed with brine and concentrated. The concentrate was flash chromatographed on silica gel with 20% ethyl acetete/hexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In dichloromethane; at 0 - 20℃; for 2.66667h; | To a chilled (0C) solution of 1-phenyl-l-cyclopropanemethanol (1.6 g, 10.8 mmol) and triethylamine (1.8 mL, 13 mmol) in dichloromethane (20 mL) was added dropwise neat CH3SO2C1 (1 mL, 13 mmol). The reaction mixture was stirred at 0C for 40 min and then was allowed to warm to r. t. and further stirred for another 2 h. The reaction mixture was further diluted with dichloromethane (40 mL) and washed with water (30 mL). The aqueous layer was separated and extracted thrice more with dichloromethane (3 x 20 mL). The organic extracts were combined, dried over anhydr. MgS04 and concentrated in vacuo to yield quantitatively the corresponding activated alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; at 0 - 20℃; | Reference Example 624'-({2-methyl-5-oxo-4-[(1-phenylcyclopropyl)methyl]-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrileTo a solution of 4'-[(2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (1.5 g), <strong>[31729-66-5](1-phenylcyclopropyl)methanol</strong> (0.87 g) and tributylphosphine (2 mL) in THF (100 mL) was added 1,1'-(azodicarbonyl)dipiperidine (2 g) at 0 C., and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogensulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.43 g, 21%).1H NMR (300 MHz, CHLOROFORM-d) δ 0.94 (d, J=1.5 Hz, 4H), 1.02 (t, J=7.3 Hz, 3H), 1.66-1.77 (m, 2H), 2.53 (s, 3H), 3.06-3.15 (m, 2H), 4.02 (s, 2H), 4.54 (s, 2H), 7.11-7.32 (m, 7H), 7.37-7.49 (m, 4H), 7.59-7.68 (m, 1H), 7.72-7.80 (m, 1H) |
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