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[ CAS No. 590-67-0 ] {[proInfo.proName]}

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Product Details of [ 590-67-0 ]

CAS No. :590-67-0 MDL No. :MFCD00003857
Formula : C7H14O Boiling Point : -
Linear Structure Formula :- InChI Key :VTBOTOBFGSVRMA-UHFFFAOYSA-N
M.W : 114.19 Pubchem ID :11550
Synonyms :

Safety of [ 590-67-0 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P210-P261-P280-P305+P351+P338 UN#:1325
Hazard Statements:H228-H302+H312+H332-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 590-67-0 ]

* 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 [ 590-67-0 ]

[ 590-67-0 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 590-67-0 ]
  • [ 931-77-1 ]
YieldReaction ConditionsOperation in experiment
67% With hydrogen bromide; lithium bromide; In water; at 0 - 23℃; Procedure descripted by Dudnik et al.3 A solution of the alcohol (5.19 g, 45.4mmol, 1.0 equiv) in 48 wt% aqueous HBr (17.0 ml) was cooled to 0 C, followed by the addition of LiBr (7.89 g, 90.8mmol, 2.0 equiv) at 0 C. The reaction mixture was allowed to warm to 23 C and stirred at this temperature untilcompletion of reaction. The reaction mixture was diluted with ether, washed with water, saturated sodium bicarbonateand brine. The organic layer was dried over sodium sulfate, concentrated in vacuo. The residue was purified bydistillation at 68 C at 50 mmHg to afford the title compound as a clear liquid (5.40 g, 30.5 mmol, 67%).
  • 2
  • [ 590-67-0 ]
  • [ 108-24-7 ]
  • [ 16737-30-7 ]
YieldReaction ConditionsOperation in experiment
38% With iron(III) p-toluenesulfonate hexahydrate; In acetonitrile; at 0 - 20℃; for 21h; General procedure: A suspension of p-nitrobenzyl alcohol (0.486 g, 3.18 mmol) and acetic anhydride (0.421 g, 0.390 mL, 4.13 mmol) in CH3CN (5 mL) was stirred at room temperature as Fe(OTs)3·6H2O (43.1 mg, 0.0636 mmol, 2.0 mol %) was added. The progress of the reaction was followed by gas chromatography. After 45 min, CH3CN was removed on a rotary evaporator, and then aqueous 10% Na2CO3 (5 mL) was added to the residue and stirred for 10 min. The reaction mixture was extracted with ethyl acetate (2 × 20 mL). The combined organic layers were washed with saturated NaCl (15 mL), dried (Na2SO4) and concentrated on a rotary evaporator to yield 0.61 g (98%) of a yellow solid that was identified as p-nitrobenzyl acetate and was determined to be 97% pure by GC, 1H NMR, and 13C spectroscopy.
Reference: [1]Journal of Organic Chemistry,1998,vol. 63,p. 2342 - 2347
[2]Synlett,2003,p. 1805 - 1808
[3]Tetrahedron Letters,2003,vol. 44,p. 6749 - 6753
[4]Synlett,2004,p. 627 - 630
[5]Tetrahedron,1990,vol. 46,p. 1839 - 1848
[6]Journal of Organic Chemistry,2003,vol. 68,p. 4951 - 4954
[7]Chemical Communications,2003,p. 1896 - 1897
[8]Journal of Organic Chemistry,1996,vol. 61,p. 4560 - 4567
[9]Synlett,2001,p. 519 - 520
[10]Synthetic Communications,2009,vol. 39,p. 4384 - 4395
[11]Monatshefte fur Chemie,2013,vol. 144,p. 369 - 374
[12]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2005,vol. 44,p. 201 - 203
[13]Tetrahedron Letters,2006,vol. 47,p. 7263 - 7265
[14]Journal of the Chemical Society. Chemical communications,1987,p. 114 - 115
[15]Monatshefte fur Chemie,2004,vol. 135,p. 279 - 282
[16]Synthetic Communications,2000,vol. 30,p. 1319 - 1329
[17]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 1999 - 2002
[18]Synthesis,2004,p. 111 - 115
[19]Tetrahedron Letters,2003,vol. 44,p. 3521 - 3525
[20]Tetrahedron Letters,2012,vol. 53,p. 6946 - 6949
[21]Journal of the American Chemical Society,1959,vol. 81,p. 651,654
[22]Tetrahedron,1978,vol. 34,p. 2069 - 2076
[23]Journal of Organic Chemistry,1985,vol. 50,p. 3928 - 3930
[24]Tetrahedron Letters,1998,vol. 39,p. 8919 - 8922
[25]Journal of Organic Chemistry,1999,vol. 64,p. 9430 - 9443
[26]Organic and biomolecular chemistry,2003,vol. 1,p. 4254 - 4261
[27]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 3460 - 3468
[28]Organic Letters,2002,vol. 4,p. 737 - 740
[29]Macromolecules,2005,vol. 38,p. 5411 - 5415
[30]Organic Letters,2007,vol. 9,p. 401 - 404
[31]Chemistry - A European Journal,2010,vol. 16,p. 2350 - 2354
  • 6
  • [ 29800-89-3 ]
  • [ 590-67-0 ]
  • [ 130275-92-2 ]
  • 7
  • [ 4952-03-8 ]
  • [ 624-29-3 ]
  • [ 110-43-0 ]
  • [ 590-67-0 ]
  • [ 16980-60-2 ]
  • [ 16980-61-3 ]
YieldReaction ConditionsOperation in experiment
With boric acid tributyl ester at 125 - 150℃; other reagent: CoSt2;
  • 8
  • [ 4952-03-8 ]
  • [ 473-55-2 ]
  • [ 61585-35-1 ]
  • [ 110-43-0 ]
  • [ 590-67-0 ]
  • [ 98-55-5 ]
  • [ 473-54-1 ]
  • [ 473-54-1 ]
  • 9
  • [ 590-67-0 ]
  • [ 94124-39-7 ]
  • [ 94124-62-6 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine In N,N-dimethyl-formamide for 12h; Ambient temperature;
  • 10
  • [ 590-67-0 ]
  • [ 50775-02-5 ]
YieldReaction ConditionsOperation in experiment
95% With bromine; potassium carbonate In chloroform at 0℃; for 5h;
86% With [bis(acetoxy)iodo]benzene; sodium bromide In acetonitrile at 20℃; for 10h; Inert atmosphere; Irradiation;
70% With magnesium bromide hexahydrate; tetramethyl ammoniumhydroxide In acetic acid methyl ester; water at 0℃; for 1.6h; Inert atmosphere; Electrolysis; Irradiation;
62% With pyridine; lead(IV) acetate; sodium bromide In benzene at 80℃; for 3h;
60% With N-Bromosuccinimide; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; [bis(acetoxy)iodo]benzene In tetrachloromethane; water at 20℃; for 61h; Irradiation;
47 % Turnov. With pyridine; lead(IV) acetate; lithium bromide In benzene at 80℃; for 3h; other MBr;
With bromine; potassium carbonate In chloroform at 0℃; for 5h;

  • 12
  • [ 82166-21-0 ]
  • [ 589-91-3 ]
  • [ 583-59-5 ]
  • [ 590-67-0 ]
  • [ 591-23-1 ]
YieldReaction ConditionsOperation in experiment
1: 24% 2: 20% 3: 3% 4: 18% With iodosylbenzene In benzene for 2h; Ambient temperature; pAr = 1 atm; Further byproducts given. Title compound not separated from byproducts;
1: 24% 2: 18% 3: 3% 4: 20% With iodosylbenzene In benzene for 2h; Ambient temperature; pAr= 1 atm; Further byproducts given. Title compound not separated from byproducts;
With peracetic acid In acetonitrile at 30℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 25℃; for 0.25h; Yield given. Further byproducts given. Yields of byproduct given;
With air; dihydrogen peroxide In acetonitrile at 75℃;
With perchloric acid; dihydrogen peroxide In water; acetonitrile; <i>tert</i>-butyl alcohol at 59.84℃; for 1h; regioselective reaction;
1: 47.7 μmol 2: 20.2 μmol 3: 21.8 μmol 4: 8.6 μmol With [(chlorido)tris{(4,4-dimethyloxazolin-2-yl)methyl}aminenickel(II)] tetraphenylborate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; Inert atmosphere; Schlenk technique;

  • 13
  • [ 590-67-0 ]
  • [ 591-49-1 ]
  • [ 16737-30-7 ]
YieldReaction ConditionsOperation in experiment
1: 91% 2: 9% With acetic anhydride; scandium tris(trifluoromethanesulfonate) In acetonitrile at -20℃; for 5h;
  • 14
  • [ 106-41-2 ]
  • [ 590-67-0 ]
  • [ 111008-55-0 ]
YieldReaction ConditionsOperation in experiment
44% With methanesulfonic acid; In dichloromethane; for 24h;Reflux; 5.1: 4-bromo-2-(1-methylcyclohexyl)-phenol 2 ml (31 mmol) of methanesulfonic acid are added to a solution of 4.7 g (41 mmol) of <strong>[590-67-0]1-<strong>[590-67-0]methylcyclohexanol</strong></strong> and 7 g (40 mmol) of 4-bromophenol in 25 ml of dichloromethane and the mixture is heated under reflux for 24 hours. After cooling to room temperature, the reaction medium is washed with water and then with a saturated sodium bicarbonate solution. The organic phase is dried on magnesium sulfate then filtered and evaporated. The crude residue obtained is purified by silica gel chromatography eluted with a 97/3 heptane/ethyl acetate mixture. 4.7 g (44%) of 4-bromo-2-(1-methyl-cyclohexyl)-phenol are obtained.
With sulfuric acid; acetic anhydride; In n-heptane; at 20℃; for 16h; Example 6; [4-Bromo-2-(1-methylcyclohexyl)phenoxy]acetic acid; 6a) Acetic anhydride (1.1 mL, 11.7 mmol) is added slowly to a mixture of <strong>[590-67-0]1-<strong>[590-67-0]methylcyclohexanol</strong></strong> (1.14 g, 10 mmol) and concentrated H2S04 (0.297 mL) in heptane (5 mL), followed by 4-bromophenol (1.73 g, 10 mmol). The reaction is stirred at ambient temperature for 16 hours and the solvent is evaporated. Water is added to the residue, the pH is adjusted to 7 with saturated aqueous NaHC03 and the solution is extracted with ether. The organic phase is dried (MgS04), evaporated and purified by flash chromatography (5: 1 EtOAc-isohexane elution) to afford 4-bromo-2-(1-methylcyclohexyl)phenol, [M-H]- 268.
  • 15
  • [ 108-22-5 ]
  • [ 590-67-0 ]
  • [ 16737-30-7 ]
YieldReaction ConditionsOperation in experiment
81% With toluene-4-sulfonic acid; In dichloromethane; at 60℃; for 15h; General procedure: A mixture of the alcohol 1 (1 mmol), isopropenyl acetate (0.45 mL, 4 mmol) and p-TsOH (4 mg, 0.02 mmol) in dichloromethane or acetonitrile (4 mL) was stirred the indicated temperature (see Tables 1 and 2). Reaction times ranged from 16 to 36 h. After completion of the reaction (TLC monitoring) the mixture was poured into 10 mL of 10% aqueous sodium hydrogen carbonate solution. The aqueous phase was extracted with ethyl acetate (3 × 10 mL) and the combined organic phases were washed with 10 mL of brine, dried over sodium sulfate and then evaporated under vacuum. Purification by silica gel column chromatography afforded the pure acetyl ester 2. Physical and spectral data of known compounds were consistent with the ones reported in literature. Physical and spectral data of not previously described compounds are reported below.
  • 16
  • [ 590-67-0 ]
  • [ 3674-06-4 ]
  • (S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid 1-methyl-cyclohexyl ester [ No CAS ]
  • 17
  • [ 7782-77-6 ]
  • [ 3218-02-8 ]
  • [ 590-67-0 ]
  • [ 502-41-0 ]
  • [ 100-49-2 ]
  • 20
  • [ 524-38-9 ]
  • [ 590-67-0 ]
  • 2-((1-methylcyclohexyl)oxy)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroborane diethyl ether; In dichloromethane; (a) N-(1-Methylcyclohexyloxy)phthalimide .- The title compound was prepared in a manner similar to that described for Example 1(a). Reaction of N-hydroxyphthalimide (8.15g), <strong>[590-67-0]1-<strong>[590-67-0]methylcyclohexanol</strong></strong> (6.21ml) and boron trifluoride etherate (4.95ml) in dry dichloromethane in the presence of 4A molecular sieves gave the title compound (3.40g), m.p. 98-99C; numax(KBr) 1785, 1742, 1611, 1465, 879, 709cmmin1; deltaH(CDCl3) 1.1-2.3 (13H,m, incorporating singlet 1.33), 7.7-8.2 (4H,m); m / z CI (NH3 gas) MNH 4+, 277 and MH +, 260.
  • 21
  • [ 82166-21-0 ]
  • [ 583-59-5 ]
  • [ 590-67-0 ]
  • [ 591-23-1 ]
  • [ 100-49-2 ]
  • 22
  • [ 82166-21-0 ]
  • [ 590-67-0 ]
  • [ 100-49-2 ]
YieldReaction ConditionsOperation in experiment
General procedure: The alkane oxidations were typically carried out in air in thermostated (50 C) Pyrex cylindrical vessels or round bottom flasks with vigorous stirring and using MeCN as solvent (up to 5.0 mL totalvolume). Typically, the catalyst precursor 1 was introduced intothe reaction mixture in the form of a stock solution in acetonitrile(2.5×10-4 M). Then PCA (optional) was added as a solid or in theform of a stock solution in MeCN (0.44 M). The alkane substrate, typically cyclohexane (0.25 mL, 2.3 mmol) was then introduced, andthe reaction started when hydrogen peroxide (50% in H2O, 0.68 mL,11 mmol) was added in one portion. The final concentrations of the reactants in the reaction mixture were as follows: catalystprecursor 1 (5×10-6 -5×10-4 M), PCA (0-0.005 M), substrate(0.46 M) and H2O2 (2.2 M). The samples were analysed by GC using nitromethane (0.05 mL) as an internal standard. Attribution of peaks was made by comparison with chromatograms of authenticsamples. Chromatographic analyses were undertaken by usinga Fisons Instruments GC 8000 series gas chromatograph (He ascarrier gas) with a BP20/SGE (30 m×0.22 mm×0.25 m) capillarycolumn (FID detector) and the Jasco-Borwin v.1.50 software. Since the oxygenation of alkanes often gives rise to the formationof the corresponding alkyl hydroperoxides as the main primaryproducts, the quantification was performed by a method developedby Shul?pin [12-14]. For precise determination of oxygenate concentrations only data obtained after reductions of the reactionsample with PPh3 were usually used, taking into account that theoriginal reaction mixture typically contained the three products:alkyl hydroperoxide (as the primary product), ketone and alcohol.The oxidations of gaseous alkanes were carried out in a 13 mLstainless steel autoclave, equipped with a Teflon-coated magneticstirring bar. In a typical experiment, after additions of all liquid (inthe form of stock solutions in acetonitrile) and solid reagents, theautoclave was closed and pressurized with 0.7-20.0 atm of gaseous alkane (typically 20.0, 6.0, or 0.7 atm of CH4 and C2H6, C3H8, or n-C4H10, respectively). The reaction mixture was stirred for 4 h at 50 C using a magnetic stirrer and an oil bath, whereupon it wascooled in an ice bath, degassed, opened and transferred to a flaskfor GC analysis. In the oxidations of gaseous alkanes, traces of acetic acid were also detected due to partial oxidation of the MeCN solvent
  • 23
  • [ 590-67-0 ]
  • [ 185331-69-5 ]
  • 2-(1-methylcyclohexyloxy)-1-bromo-4-nitrobenzene [ No CAS ]
  • 24
  • [ 937184-70-8 ]
  • [ 590-67-0 ]
  • [ 2584-47-6 ]
  • [ 1020186-18-8 ]
YieldReaction ConditionsOperation in experiment
94% With camphor-10-sulfonic acid In dichloromethane at 20℃; for 67h;
  • 25
  • [ 167688-16-6 ]
  • [ 590-67-0 ]
  • [ 1314045-30-1 ]
YieldReaction ConditionsOperation in experiment
56% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0℃; for 1h; General procedure: To a 5 mL round-bottom flask with a mixture of 1,3-diarylpropynes (0.25 mmol) and alcohol (0.3 mmol) in CH2Cl2 (1 mL), DDQ (0.27 mmol) was added at 0 C. The resulting mixture was stirred for 1 h. Purification was done by column chromatography on silica gel (petroleum ether/ethyl acetate=20/1), and the fraction with an Rf=0.6 was collected to give the desired product.
  • 26
  • [ 1020186-18-8 ]
  • [ 590-67-0 ]
YieldReaction ConditionsOperation in experiment
93% With 4,4'-bipyridine; (phthalocyaninato)iron(II); oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 80℃; under 3000.3 Torr; for 20h;Autoclave; In 300 ml polytetrafluoroethylene liner in pressure, by adding 1mmol the protection of the benzyl methyl cyclohexanol (formula (5)), 20 ml toluene, 0.15mmol of DDQ, 0.15mmol the FeIIPc, 0.15mmol the 4, the 4 [...] -bpy, closed pressure, oxygen charging to the pressure is 0.4 MPa, the pressure put into the pre-heating to 80 C in oil bath, reaction 20h. After the temperature and to pressure relief, organic gas phase chromatography (GC) analysis, the conversion is 100%, the product selectivity is 98%. A silica gel column, to volume ratio of 1:3 a mixture of petroleum ether and ethyl acetate as eluant, methyl cyclohexanol separation yield is 93%.
  • 27
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  • [ 7731-29-5 ]
  • [ 7731-28-4 ]
  • [ 7443-55-2 ]
  • [ 5454-79-5 ]
  • [ 589-92-4 ]
  • [ 583-60-8 ]
  • [ 625-96-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl cyclohexane With tert.-butylhydroperoxide; (OC2H4)(OHC2H4)NC2H4N(C2H4OH)Cu(thiocyanate) In water; acetonitrile at 70℃; for 2h; Stage #2: With triphenylphosphine In water; acetonitrile regioselective reaction;
  • 28
  • [ 82166-21-0 ]
  • [ 590-67-0 ]
  • [ 7731-29-5 ]
  • [ 7731-28-4 ]
  • [ 5454-79-5 ]
  • [ 589-92-4 ]
  • [ 583-60-8 ]
  • [ 625-96-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl cyclohexane With tert.-butylhydroperoxide; (OC2H4)(OHC2H4)NC2H4N(C2H4OH)Cu(thiocyanate) In water; acetonitrile at 70℃; for 7h; Stage #2: With triphenylphosphine In water; acetonitrile regioselective reaction;
  • 29
  • [ 82166-21-0 ]
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  • [ 7731-29-5 ]
  • [ 7731-28-4 ]
  • [ 7443-52-9 ]
  • [ 7443-70-1 ]
  • [ 7443-55-2 ]
  • [ 5454-79-5 ]
  • [ 589-92-4 ]
  • [ 583-60-8 ]
  • [ 100-49-2 ]
  • [ 2043-61-0 ]
  • [ 591-24-2 ]
  • 30
  • [ 82166-21-0 ]
  • [ 589-91-3 ]
  • [ 583-59-5 ]
  • [ 590-67-0 ]
  • [ 591-23-1 ]
  • [ 589-92-4 ]
  • [ 100-49-2 ]
  • [ 591-24-2 ]
  • 31
  • [ 82166-21-0 ]
  • [ 603-35-0 ]
  • [ 590-67-0 ]
  • [ 100-49-2 ]
  • 32
  • [ 590-67-0 ]
  • [ 7693-46-1 ]
  • [ 40044-37-9 ]
YieldReaction ConditionsOperation in experiment
42% In a round bottomed flask equipped with a magnetic stirrer and a dropping funnel, CH2C12 (20 mL) was loaded followed by l-<strong>[590-67-0]methylcyclohexanol</strong> (2 mL, 16.1 mmol) and pyridine (2.5 mL, 32.3 mmol). The clear solution was chilled at 0C on an ice bath, and after lOmin a solution / iitrophenylchloroformate (3.25 g, 16.1 mmol) in CH2C12 (10 mL) was added dropwise in a period of lOmin. A white precipitate appeared almost immediately, which changed to yellow upon leaving the mixture under stirring at rt overnight. Water (20 mL) was then added and the mixture was stirred for lOmin. The two phases were separated and the organic phase was washed again with water (20 mL) then dried over Na2S04. Solvents were removed under vacuum to give an oil which was purified by typical chromatography eluting with petroleum ether/AcOEt (from 70:30 to 1 :1). The title compound was obtained (1.9 g, 42%), as light yellow oil, which was used in the next step without further purification. NMR (CDCI3): delta 1.25-1.65 (m, 8H), 1.57 (s, 3H), 2.20 (m, 2H), 7.36 (d, J= 9.1 Hz, 2H), 8.26 (d, J= 9.1 Hz, 2H).
42% Step 1. Preparation of (1-methylcyclohexyl)-(4-nitrophenyl)-carbonate In a round bottomed flask equipped with a magnetic stirrer and a dropping funnel, CH2Cl2 (20 mL) was loaded followed by <strong>[590-67-0]1-<strong>[590-67-0]methylcyclohexanol</strong></strong> (2 mL, 16.1 mmol) and pyridine (2.5 mL, 32.3 mmol). The clear solution was chilled at 0 C. on an ice bath, and after 10 min a solution p-nitrophenylchloroformate (3.25 g, 16.1 mmol) in CH2Cl2 (10 mL) was added dropwise in a period of 10 min. A white precipitate appeared almost immediately, which changed to yellow upon leaving the mixture under stirring at rt overnight. Water (20 mL) was then added and the mixture was stirred for 10 min. The two phases were separated and the organic phase was washed again with water (20 mL) then dried over Na2SO4. Solvents were removed under vacuum to give an oil which was purified by typical chromatography eluting with petroleum ether/AcOEt (from 70:30 to 1:1). The title compound was obtained (1.9 g, 42%), as light yellow oil, which was used in the next step without further purification. 1H NMR (CDCl3): delta 1.25-1.65 (m, 8H), 1.57 (s, 3H), 2.20 (m, 2H), 7.36 (d, J=9.1 Hz, 2H), 8.26 (d, J=9.1 Hz, 2H).
  • 33
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  • [ 590-67-0 ]
  • [ 19043-03-9 ]
  • [ 583-59-5 ]
  • [ 24965-94-4 ]
  • [ 7731-29-5 ]
  • [ 7731-28-4 ]
  • [ 24965-91-1 ]
  • [ 589-92-4 ]
  • [ 583-60-8 ]
  • [ 100-49-2 ]
  • [ 2043-61-0 ]
  • [ 591-24-2 ]
  • 34
  • [ 82166-21-0 ]
  • cis-3-methylcyclohexanol [ No CAS ]
  • trans-3-methylcyclohexanol [ No CAS ]
  • cis-4-methylcyclohexanol [ No CAS ]
  • trans-4-methylcyclohexanol [ No CAS ]
  • [ 590-67-0 ]
  • [ 100-49-2 ]
  • (Z)-2-methylcyclohexanol [ No CAS ]
  • trans-2-methylcyclohexanol [ No CAS ]
  • 35
  • [ 590-67-0 ]
  • [ 17429-02-6 ]
  • [ 68165-43-5 ]
  • 36
  • [ 1189-71-5 ]
  • [ 590-67-0 ]
  • CH4O3S*C16H24N2O2 [ No CAS ]
  • 1-methylcyclohexyl (3aR,5S,7aS)-3-benzyl-5-(dimethylcarbamoyl)-2,2-dioxooctahydro-1H-2,1,3-benzothiazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Example 10 Preparation of 1-methylcyclohexyl (3aR,5S,7aS)-3-benzyl-5-(dimethylcarbamoyl)-2,2-dioxooctahydro-1H-2,1,3-benzothiazole-1-carboxylate (Formula (4-A) Wherein R1=CR1aR1bR1c; R1a,R1b=H; and R1c is phenyl, R2=1-methylcyclohexyl or Formula (4-A4)) To a solution of <strong>[590-67-0]1-<strong>[590-67-0]methylcyclohexanol</strong></strong> (96%, 10.13 g, 85.2 mmol) in acetonitrile (30 mL) maintained at about -8 C. was added a solution of chlorosulfonylisocyanate (98%, 12.29 g, 85.1 mmol) in acetonitrile (30 mL). To the resulting clear, colorless solution was added a solution of triethylamine (99.5%, 24.93 g, 245.1 mmol) in acetonitrile (30 mL) at about -10 C. The solution changed to a white suspension after half of the addition, gradually becoming thick at the end of the addition. To the resulting suspension was added triethylamine (5.22 g, 51.33 mmol) and a solution of (1S,3R,4R)-3-(phenylmethyl)amino-4-hydroxy-N,N-dimethylcyclohexanecarboxamide mesylate (95%, 13.36 g, 34.1 mmol) in acetonitrile (50 mL). The resulting thinner suspension was stirred at about -2 C. for about 30 minutes, before the temperature was allowed to increase to room temperature. Following refluxing for 4 hours, the mixture was concentrated to about 40 mL under reduced pressure followed by slow addition of water (100 mL) under stirring. The resulting suspension was cooled to about 0 C. and stirred for about 1 hour. The product was collected by filtration, washed with cold water (2*20 mL), and dried in vacuo at about 45 C. to afford 1-methyl-cyclohexyl(3aR,5S,7aS)-3-benzyl-5-(dimethylcarbamoyl)-2,2-dioxooctahydro-1H-2,1,3-benzothiazole-1-carboxylate (9.24 g, 57% yield).
  • 37
  • [ 82166-21-0 ]
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  • [ 590-67-0 ]
YieldReaction ConditionsOperation in experiment
1: 18% 2: 6% With [Fe4III(μ-O)2(μ-acetate)6(2,2'-bipyridine)2(H2O)2](NO3-)(OH-); dihydrogen peroxide; acetic acid In water; acetonitrile at 32℃; for 3h; Overall yield = 31 %Spectr.; 2.4. C-H activation analysis by the oxido-acetato-bridged tetraironcomplex (1) General procedure: Conversion of cyclooctane: Cyclooctane (228 mg, 268 ml,2 mmol) was added to a solution of 1 (0.04 mmol) in MeCN:aceticacid (1.5:0.5 ml) in over all catalyst 1: substrate: oxidant0.04:200:500). After the addition of H2O2 (33% in H2O; 454 mL,5.0 mmol), the reaction mixture was heated at 32 °C for 3 h. Themixturewas then allowed to cool to room temperature. The organicphase was extracted with Et2O (3 x 1 ml), washed with brine anddried (MgSO4). After filtration, the solvents of the filtrate wereevaporated (rotary evaporator). The remaining mixture was separatedby column chromatography (silica gel; diethyl ether:pentane 1:20 as eluent) and the product was analyzed by GC-MSusing 1,2-dichlorobenzene as an internal standard.
  • 38
  • [ 82166-21-0 ]
  • [ 589-91-3 ]
  • [ 583-59-5 ]
  • [ 590-67-0 ]
  • [ 591-23-1 ]
  • [ 100-49-2 ]
  • 39
  • [ 67-56-1 ]
  • [ 590-67-0 ]
  • [ 103884-34-0 ]
YieldReaction ConditionsOperation in experiment
44% With [bis({2?[bis(propan?2?yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); methacrylic acid methyl ester; In toluene; at 140℃; under 13689.1 Torr; for 8h;Autoclave; Inert atmosphere; A 100-mL stainless steel Parr reactor equipped with a stir bar (200 rpm) was charged with 1A (81 mg, 0.2 mmol, 1 mol%), anhydrous methanol (0.8 mL, 20 mmol), <strong>[590-67-0]1-<strong>[590-67-0]methylcyclohexanol</strong></strong> (10.3 mL, 80 mmol), methyl methacrylate (8.6 mL, 80 mmol), and 10 mL of anhydrous toluene. The resulting mixture was purged three times with N2 (~150 psig) to remove air and then heated to 140C under 250 psig of N2 pressure for 8 hours. After that, the reactor was allowed to cool to room temperature and N2 gas was slowly vented inside the hood. The sample was analyzed by GC to obtain percent yield and selectivity of the corresponding formate ester. The results are reported in Table 4.
  • 40
  • [ 590-67-0 ]
  • [ 920-46-7 ]
  • 1-methylcyclohexyl methylacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.6% With dmap; 10H-phenothiazine; triethylamine; In dichloromethane; at 5 - 15℃; for 3h;Inert atmosphere; The second step: To a 2 L four-necked flask was added dichloromethane (994 g), <strong>[590-67-0]1-<strong>[590-67-0]methylcyclohexanol</strong></strong> (150 g), triethylamine (332.3 g), phenothiazine (1.5 g), DMAP under nitrogen at 25 C. (4-dimethylaminopyridine) (1.5 g).The temperature was lowered to 5 C, the temperature was controlled at 5 ± 5 C, and methacryloyl chloride (206 g) was added dropwise to the reaction flask. When the mixture was added dropwise, a large amount of white mist appeared in the reaction flask, and the reaction liquid gradually changed from light green to yellow. A large amount of solid was precipitated and the addition was completed in about 1 hour.The temperature was raised to 15 ± 5 C, and the reaction was kept for 2 hours, (central control 1, raw material content GC After completion of the reaction, the mixture was quenched by dropwise addition of 350 g of water at a temperature of 20 C or lower, stirred for 15 min, and layered.The upper aqueous layer was treated as waste liquid, and the lower organic layer was added with 6% hydrochloric acid solution (85 g 36% hydrochloric acid, 415 g water), adjusted to pH=6-7, stirred for 15 min, layered, and the upper aqueous layer was treated with waste acid.The lower organic layer was stirred with 350 g of water for 15 min and layered.The lower organic layer is added with 2% sodium hydroxide solution (7g NaOH 343g water), the control temperature is below 20 C, sodium hydroxide solution is added to adjust the pH>10, layering, the lower organic layer is sampled GC (central control 2, retention time 5.5min) If the impurity content is The lower organic phase was dried by adding 30 g of anhydrous sodium sulfate, and the water was taken for measurement (central control 3, moisture The organic phase was transferred to a 2 L single-mouth bottle and 0.1 g of phenothiazine was added thereto. The temperature of the water bath was controlled at 25 to 30 C, and concentrated to obtain 239.3.g of a pale yellow liquid (central control 4, dissolved GC The crude product was transferred to a 500 mL single-mouth bottle and supplemented with 0.1 g of phenothiazine, and subjected to vacuum distillation using a 20 cm glass spring packed column.When the oil bath is at 90 C, the top temperature is at 64-68 C, and the former fraction is taken.After the temperature was stabilized at about 68 C for 5 minutes, the main fraction was taken to obtain 190 g of 1-methylcyclohexyl methacrylate, a colorless transparent liquid, and the molar yield was 85.6% (central control 5, product GC purity >99%).
  • 41
  • [ 492-37-5 ]
  • [ 590-67-0 ]
  • C15H22O [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With 2,4,6-trimethyl-pyridine; silver(I) hexafluorophosphate; tert-butylammonium hexafluorophosphate(V); In dichloromethane; at 20℃; for 3h;Electrolysis; Molecular sieve; General procedure: With no precautions to exclude air or moisture, the ElectraSyn vial (5 ml) with a stir bar was charged with carboxylic acid (0.2 mmol, 1.0 equiv.), alcohol (0.6 mmol, 3.0 equiv.), 2,4,6-collidine (0.6 mmol, 3.0 equiv.), nBu4NPF6 (0.3 mmol, 1.5 equiv.), 3 A molecular sieves (150 mg), AgPF6 (0.3 mmol, 1.5 equiv.) and CH2Cl2 (3.0 ml). The ElectraSyn vial cap equipped with anode (graphite) and cathode (graphite) were inserted into the mixture. After pre-stirring for 15 min, the reaction mixture was electrolysed at a constant current of 10 mA for 3 h. The ElectraSyn vial cap was removed, and electrodes were rinsed with Et2O (2 ml), which was combined with the crude mixture. Then, the crude mixture was further diluted with Et2O (30 ml). The resulting mixture was washed with 2 M HCl (20 ml) and NaHCO3 (aq.) (20 ml), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by preparative thin-layer chromatography to furnish the desired product. Full experimental details and characterization of new compounds can be found in the Supplementary Information.
  • 42
  • [ 578-58-5 ]
  • [ 590-67-0 ]
  • C15H22O [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With ferric(III) bromide; hydrogen bromide In water monomer; 1,2-dichloro-ethane at 50℃;
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