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[ CAS No. 543-49-7 ] {[proInfo.proName]}

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Chemical Structure| 543-49-7
Chemical Structure| 543-49-7
Structure of 543-49-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 543-49-7 ]

CAS No. :543-49-7 MDL No. :MFCD00004587
Formula : C7H16O Boiling Point : -
Linear Structure Formula :- InChI Key :CETWDUZRCINIHU-UHFFFAOYSA-N
M.W : 116.20 Pubchem ID :10976
Synonyms :
s-Heptyl alcohol

Calculated chemistry of [ 543-49-7 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.92
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.29
Log Po/w (XLOGP3) : 2.31
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.75
Solubility : 2.06 mg/ml ; 0.0177 mol/l
Class : Very soluble
Log S (Ali) : -2.37
Solubility : 0.492 mg/ml ; 0.00424 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.69
Solubility : 2.36 mg/ml ; 0.0203 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 543-49-7 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P280-P305+P351+P338 UN#:1987
Hazard Statements:H225-H312-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 543-49-7 ]

* 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 [ 543-49-7 ]

[ 543-49-7 ] Synthesis Path-Downstream   1~37

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YieldReaction ConditionsOperation in experiment
1: 27% 2: 26% 3: 14% 4: 25% With [PPh4]2[MnV(N)(CN)4]; tetrabutylammonium periodite; acetic acid In 2,2,2-trifluoroethanol at 23℃; Inert atmosphere;
1: 12.5% 2: 4% 3: 1% 4: 15% With iodosylbenzene In benzene for 2h; Ambient temperature; anaerobic cond.; Further byproducts given;
With iodosylbenzene In benzene at 20℃; Yield given. Further byproducts given. Yields of byproduct given;
With iodosylbenzene; <silica-O-Si-(CH2)3NHC6F4>(C6F5)3PMnCl (P = porphyrin) In dichloromethane at 20℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With iodosylbenzene In dichloromethane; acetonitrile at 20℃; for 2h; Yield given. Further byproducts given. Yields of byproduct given;
With iodosylbenzene In benzene at 20℃; Yield given. Further byproducts given. Yields of byproduct given;
In benzene at 20℃; oxidation with cumylhydroperoxide or with iodosobenzene in the presence of various Fe(III)(porphyrin)(Cl) complexes as catalysts;
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide In acetic acid at 30℃;

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  • [ 111-70-6 ]
YieldReaction ConditionsOperation in experiment
1: 1.5% 2: 29.5% 3: 28% 4: 11% With iron (III) meso-tetrakis (2,6-dichlorophenylporphyrin-β-octabromo)chloride; iodosylbenzene In dichloromethane at 20℃; for 1h; other iron-porphyrins; other alkane;
With iodosylbenzene In benzene at 25℃; for 7h; other catalysts and regioselectivity investigated; various oxidants also investigated;
With iodosylbenzene at 25℃; other catalysts, oxidant;
With ammonium acetate; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); dihydrogen peroxide In dichloromethane; acetonitrile for 2h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given;
Stage #1: n-heptane With air; dihydrogen peroxide In water; acetonitrile at 23℃; for 51h; Stage #2: With triphenylphosphine In water; acetonitrile Further byproducts given;
With air; dihydrogen peroxide In acetonitrile at 60℃;
With pyridine; 2-pyrazylcarboxylic acid; dihydrogen peroxide In acetonitrile at 40℃; for 2.5h;
Stage #1: n-heptane With aluminum(III) nitrate nonahydrate; dihydrogen peroxide In water; acetonitrile at 70℃; Stage #2: With triphenylphosphine In water; acetonitrile
Stage #1: n-heptane With tert.-butylhydroperoxide; OCu4(N(CH2CH2O)3)4(BOH)4(2+)*2BF4(1-)=[OCu4(N(CH2CH2O)3)4(BOH)4][BF4]2 In water; acetonitrile at 50℃; for 0.5h; Stage #2: With triphenylphosphine regioselective reaction;
1: 55 %Chromat. 2: 10 %Chromat. 3: 7 %Chromat. 4: 27 %Chromat. With dihydrogen peroxide; sodium hydrogencarbonate In water; acetonitrile at 80℃; for 5h;
Stage #1: n-heptane With 2-pyrazylcarboxylic acid; [{VO(EtO)(EtOH)}2(1κ2O,κN:2κ2O,κN-bis(2-hydroxybenzylidene)oxalohydrazonic acid)]·2H2O; dihydrogen peroxide In water; acetonitrile at 50℃; Stage #2: With triphenylphosphine 2.5. Peroxidative oxidation of alkanes 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
With ferrocene; dihydrogen peroxide; trifluoroacetic acid In water; acetonitrile at 40℃; for 2h;
With (PhGeO<SUB>2</SUB>)<SUB>12</SUB>Cu<SUB>2</SUB>Fe<SUB>5</SUB>(O)OH(PhGe)<SUB>2</SUB>O<SUB>5</SUB>(2,2'-bipyridine)<SUB>2</SUB>; dihydrogen peroxide; nitric acid In acetonitrile at 50℃; for 0.0833333h;
1: 18 %Chromat. 2: 16.2 %Chromat. 3: 9.7 %Chromat. 4: 5.4 %Chromat. With iodosylbenzene; C51H13F19N4O2S(2-)*C2H3O2(1-)*Mn(3+) In acetonitrile for 1h; Darkness; 2.2. Catalytic oxidation reactions General procedure: The following procedure was adopted to assess the oxidation of different substrates catalyzed by the previously prepared metalloporphyrins: about 1.0mg of the metalloporphyrin was weighed in a 2mL thermostatic glass reactor tube equipped with a magnetic stirrer. The reactor tube was placed inside a dark recipient, and iodosylbenzene was added, to obtain a 1:10 catalyst/oxidant molar ratio. The reactor was degassed with argon for 15min, which was followed by addition of the solvent (acetonitrile, 400μL) and about 100μL of the substrate ((Z)-cyclooctene, cyclohexane or heptanes - 1:1000 catalyst/substrate molar ratio). The oxidation reactions were carried out under magnetic stirring for 1h or 24h. (Z)-cyclooctene had been previously purified by column chromatography on an alumina micro column. The reactions were quenched by addition of sodium sulfite saturated solution (approximately 0.1mol/L), to eliminate excess PhIO. The reaction mixture was transferred to a volumetric flask, and aliquots were analyzed by gas chromatography after addition of the internal standard (a solution of 99.9% octan-1-ol in acetonitrile 1.0×10-2mol/L). When the catalyst used in the reaction was insoluble (FeP6, MnP6, and CuP6), the solid catalyst was washed several times with methanol and acetonitrile after the reaction, to extract any reaction products that might have adsorbed onto the solid. The washing solutions were added to the previously separated reaction supernatant, and the contents of these combined solutions were analyzed by gas chromatography, also using octan-1-ol as internal standard. The product yields were based on the amount of PhIO added to the reactions. The molar ratio 1:10 catalyst/oxidant was estimated based on molecular mass of MP including the insoluble solids catalysts. Control experiments were also carried out in the absence of MPx using the methodology described above.
Stage #1: n-heptane With 2-pyrazylcarboxylic acid; [VOCl2(bis[N-(2,6-diisopropylphenyl)imino]acenaphthene)]; dihydrogen peroxide In water; acetonitrile Stage #2: With triphenylphosphine In water; acetonitrile regioselective reaction;
Stage #1: n-heptane With [VOCl2(bis[N-(2,6-diisopropylphenyl)imino]acenaphthene)]; dihydrogen peroxide In water; acetonitrile Stage #2: With triphenylphosphine In water; acetonitrile regioselective reaction;
With C12H8N2*C13H7NO4(2-)*Cu(2+)*H2O; dihydrogen peroxide In acetonitrile at 50℃; for 2h; regioselective reaction;
With potassium tetrachloroplatinate; Perfluorooctanoic acid; sulfuric acid; oxygen In water at 150℃; for 6h; Autoclave;

Reference: [1]Bartoli; Brigaud; Battioni; Mansuy [Journal of the Chemical Society. Chemical communications, 1991, # 6, p. 440 - 442]
[2]Cook, Bruce R.; Reinert, Thomas J.; Suslick, Kenneth S. [Journal of the American Chemical Society, 1986, vol. 108, # 23, p. 7281 - 7286]
[3]Suslick, Kenneth; Cook, Bruce; Fox, Mary [Journal of the Chemical Society. Chemical communications, 1985, # 9, p. 580 - 582]
[4]Thellend, Annie; Battioni, Pierrette; Mansuy, Daniel [Journal of the Chemical Society. Chemical communications, 1994, # 9, p. 1035 - 1036]
[5]Guerreiro; Schuchardt; Shul'pin [Russian Chemical Bulletin, 1997, vol. 46, # 4, p. 749 - 754]
[6]Shul'pin, Georgiy B.; Kudinov, Aleksandr R.; Shul'pina, Lidia S.; Petrovskaya, Elena A. [Journal of Organometallic Chemistry, 2006, vol. 691, # 5, p. 837 - 845]
[7]Jannini; Shul'pina; Schuchardt; Shul'pin [Petroleum Chemistry, 2005, vol. 45, # 6, p. 413 - 418]
[8]Location in patent: scheme or table Mandelli, Dalmo; Chiacchio, Karyna C.; Kozlov, Yuriy N.; Shul'pin, Georgiy B. [Tetrahedron Letters, 2008, vol. 49, # 47, p. 6693 - 6697]
[9]Location in patent: scheme or table Kirillova, Marina V.; Kirillov, Alexander M.; Mandelli, Dalmo; Carvalho, Wagner A.; Pombeiro, Armando J.L.; Shul'Pin, Georgiy B. [Journal of Catalysis, 2010, vol. 272, # 1, p. 9 - 17]
[10]Location in patent: experimental part Monfared, Hassan Hosseini; Abbasi, Vahideh; Rezaei, Adineh; Ghorbanloo, Massomeh; Aghaei, Alireza [Transition Metal Chemistry, 2012, vol. 37, # 1, p. 85 - 92]
[11]Gupta, Samik; Kirillova, Marina V.; Guedes Da Silva, M. Fátima; Pombeiro, Armando J.L. [Applied Catalysis A: General, 2013, vol. 460-461, p. 82 - 89]
[12]Shul'pina, Lidia S.; Kudinov, Aleksandr R.; Mandelli, Dalmo; Carvalho, Wagner A.; Kozlov, Yuriy N.; Vinogradov, Mikhail M.; Ikonnikov, Nikolay S.; Shul'pin, Georgiy B. [Journal of Organometallic Chemistry, 2015, vol. 793, p. 217 - 231]
[13]Bilyachenko, Alexey N.; Khrustalev, Victor N.; Zubavichus, Yan V.; Shul'Pina, Lidia S.; Kulakova, Alena N.; Bantreil, Xavier; Lamaty, Frédéric; Levitsky, Mikhail M.; Gutsul, Evgeniy I.; Shubina, Elena S.; Shul'Pin, Georgiy B. [Inorganic Chemistry, 2018, vol. 57, # 1, p. 528 - 534]
[14]de F. Castro, Kelly A.D.; Simões, Mário M.Q.; da Graça P.M.S. Neves, Maria; Cavaleiro, José A.S.; Ribeiro, Ronny R.; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2015, vol. 503, p. 9 - 19]
[15]Fomenko, Iakov S.; Gushchin, Artem L.; Shul'pina, Lidia S.; Ikonnikov, Nikolay S.; Abramov, Pavel A.; Romashev, Nikolay F.; Poryvaev, Artem S.; Sheveleva, Alena M.; Bogomyakov, Artem S.; Shmelev, Nikita Y.; Fedin, Matvey V.; Shul'pin, Georgiy B.; Sokolov, Maxim N. [New Journal of Chemistry, 2018, vol. 42, # 19, p. 16200 - 16210]
[16]Fomenko, Iakov S.; Gushchin, Artem L.; Shul'pina, Lidia S.; Ikonnikov, Nikolay S.; Abramov, Pavel A.; Romashev, Nikolay F.; Poryvaev, Artem S.; Sheveleva, Alena M.; Bogomyakov, Artem S.; Shmelev, Nikita Y.; Fedin, Matvey V.; Shul'pin, Georgiy B.; Sokolov, Maxim N. [New Journal of Chemistry, 2018, vol. 42, # 19, p. 16200 - 16210]
[17]Gu, Jinzhong; Wen, Min; Cai, Yan; Shi, Zifa; Arol, Aliaksandr S.; Kirillova, Marina V.; Kirillov, Alexander M. [Inorganic Chemistry, 2019, vol. 58, # 4, p. 2403 - 2412]
[18]De Vos, Dirk E.; Janssen, Michiel [Catalysis science and technology, 2020, vol. 10, # 5, p. 1264 - 1272]
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YieldReaction ConditionsOperation in experiment
1: 18% 2: 22% 3: 11% 4: 18% 5: 15% 6: 9% With iodosylbenzene In chloroform; acetonitrile at 0.26℃; for 1.5h; Darkness; regioselective reaction;
1: 15% 2: 14% 3: 7% 4: 21% 5: 15% 6: 9% With iodosylbenzene In chloroform; acetonitrile at 0.26℃; for 1.5h; Darkness; regioselective reaction;
1: 16% 2: 19% 3: 9% 4: 19% 5: 16% 6: 10% With iodosylbenzene In chloroform; acetonitrile at 0.26℃; for 1.5h; Darkness; regioselective reaction;
1: 9% 2: 10% 3: 5% 4: 18% 5: 14% 6: 9% With iodosylbenzene In chloroform; acetonitrile at 0.26℃; for 1.5h; Darkness; regioselective reaction;
With iodosylbenzene; <silica-O-Si-(CH2)3NHC6F4>(C6F5)3PFeCl (P = porphyrin) In dichloromethane at 20℃; for 1h; var. polyhalogenated metalloporphyrins covalently bound to polymeric supports; other hydrocarbons;
1: 8 % Chromat. 2: 6 % Chromat. 3: 1 % Chromat. 4: 41 % Chromat. 5: 28 % Chromat. 6: 16 % Chromat. With tert.-butylhydroperoxide In acetonitrile Ambient temperature;
With oxygen; dibenzoyl peroxide for 1h; Heating; var. time, var. conc. of benzoyl peroxide;
1: 22 %Chromat. 2: 23 %Chromat. 3: 11 %Chromat. 4: 11 %Chromat. 5: 11 %Chromat. 6: 5 %Chromat. With tert.-butylhydroperoxide; iron(III) chloride; {tetra-n-butylammonium}{osmiumnitrido(chloro)4} In dichloromethane; acetic acid at 23℃; for 0.0833333h;
1: 23 %Chromat. 2: 23 %Chromat. 3: 12 %Chromat. 4: 5 %Chromat. 5: 4 %Chromat. 6: 2 %Chromat. With [Os(VI)(N)(N,N'-bis(salicylidene)-o-cyclohexyldiamine(2-))(CH3OH)]PF6; dihydrogen peroxide In dichloromethane; acetic acid at 23℃; for 3h; Inert atmosphere; Overall yield = 69 %Chromat.;

Reference: [1]Pinto, Victor Hugo A.; Falcão, Nathália K. S. M.; Mariz-Silva, Bárbara; Fonseca, Maria Gardennia; Rebouças, Júlio S. [Dalton Transactions, 2020, vol. 49, # 45, p. 16404 - 16418]
[2]Pinto, Victor Hugo A.; Falcão, Nathália K. S. M.; Mariz-Silva, Bárbara; Fonseca, Maria Gardennia; Rebouças, Júlio S. [Dalton Transactions, 2020, vol. 49, # 45, p. 16404 - 16418]
[3]Pinto, Victor Hugo A.; Falcão, Nathália K. S. M.; Mariz-Silva, Bárbara; Fonseca, Maria Gardennia; Rebouças, Júlio S. [Dalton Transactions, 2020, vol. 49, # 45, p. 16404 - 16418]
[4]Pinto, Victor Hugo A.; Falcão, Nathália K. S. M.; Mariz-Silva, Bárbara; Fonseca, Maria Gardennia; Rebouças, Júlio S. [Dalton Transactions, 2020, vol. 49, # 45, p. 16404 - 16418]
[5]Battioni, P.; Bartoli, J. F.; Mansuy, D.; Byun, Y. S.; Traylor, T. G. [Journal of the Chemical Society. Chemical communications, 1992, # 15, p. 1051 - 1053]
[6]Menage, Stephane; Collomb-Dunand-Sauthier, Marie-Noe.; Lambeaux, Claude; Fontecave, Marc [Journal of the Chemical Society. Chemical communications, 1994, # 16, p. 1885 - 1886]
[7]Goosen, Andre; Kindermans, Sybrandus; McCleland, Cedric W.; Morgan, David H.; O'Connell, Johannes S.; Taljaard, Ben [South African Journal of Chemistry, 1997, vol. 50, # 1, p. 34 - 39]
[8]Location in patent: scheme or table Yiu, Shek-Man; Man, Wai-Lun; Lau, Tai-Chu [Journal of the American Chemical Society, 2008, vol. 130, # 32, p. 10821 - 10827]
[9]Chen, Man; Pan, Yi; Kwong, Hoi-Ki; Zeng, Raymond J.; Lau, Kai-Chung; Lau, Tai-Chu [Chemical Communications, 2015, vol. 51, # 71, p. 13686 - 13689]
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YieldReaction ConditionsOperation in experiment
With iodosylbenzene In dichloromethane; acetonitrile at 20℃; for 2h; Yield given. Further byproducts given. Yields of byproduct given;
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YieldReaction ConditionsOperation in experiment
1: 6% 2: 6% 3: 7% 4: 7% With meso-5,10,15,20-tetrakis(4-N-methylpyridiniumyl)porphyrinatomanganese(III) pentachloride; iodosylbenzene In chloroform; acetonitrile at 0.26℃; for 1.5h; Darkness; regioselective reaction;
With iodosylbenzene In dichloromethane; acetonitrile at 20℃; for 2h; Yield given. Further byproducts given. Yields of byproduct given;
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YieldReaction ConditionsOperation in experiment
With 1H-imidazole; iodosylbenzene In dichloromethane; acetonitrile for 2h; Ambient temperature; further reagent;
Stage #1: n-heptane With sodium metavanadate tetrahydrate; sulfuric acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 0.5h; Stage #2: With triphenylphosphine In water; acetonitrile
1: 15.2 %Chromat. 2: 14.4 %Chromat. 3: 8.7 %Chromat. 4: 7 %Chromat. With iodosylbenzene; C51H13ClF19FeN4O2S In acetonitrile for 24h; Darkness; 2.2. Catalytic oxidation reactions General procedure: The following procedure was adopted to assess the oxidation of different substrates catalyzed by the previously prepared metalloporphyrins: about 1.0mg of the metalloporphyrin was weighed in a 2mL thermostatic glass reactor tube equipped with a magnetic stirrer. The reactor tube was placed inside a dark recipient, and iodosylbenzene was added, to obtain a 1:10 catalyst/oxidant molar ratio. The reactor was degassed with argon for 15min, which was followed by addition of the solvent (acetonitrile, 400μL) and about 100μL of the substrate ((Z)-cyclooctene, cyclohexane or heptanes - 1:1000 catalyst/substrate molar ratio). The oxidation reactions were carried out under magnetic stirring for 1h or 24h. (Z)-cyclooctene had been previously purified by column chromatography on an alumina micro column. The reactions were quenched by addition of sodium sulfite saturated solution (approximately 0.1mol/L), to eliminate excess PhIO. The reaction mixture was transferred to a volumetric flask, and aliquots were analyzed by gas chromatography after addition of the internal standard (a solution of 99.9% octan-1-ol in acetonitrile 1.0×10-2mol/L). When the catalyst used in the reaction was insoluble (FeP6, MnP6, and CuP6), the solid catalyst was washed several times with methanol and acetonitrile after the reaction, to extract any reaction products that might have adsorbed onto the solid. The washing solutions were added to the previously separated reaction supernatant, and the contents of these combined solutions were analyzed by gas chromatography, also using octan-1-ol as internal standard. The product yields were based on the amount of PhIO added to the reactions. The molar ratio 1:10 catalyst/oxidant was estimated based on molecular mass of MP including the insoluble solids catalysts. Control experiments were also carried out in the absence of MPx using the methodology described above.
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YieldReaction ConditionsOperation in experiment
With iodosylbenzene In benzene at 20℃; Yield given. Further byproducts given. Yields of byproduct given;
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YieldReaction ConditionsOperation in experiment
With zinc borohydride; silica gel In N,N-dimethyl-formamide for 1.5h; Ambient temperature; Yield given. Yields of byproduct given;
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YieldReaction ConditionsOperation in experiment
With iodosylbenzene In dichloromethane; acetonitrile at 20℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With air; dihydrogen peroxide In acetonitrile at 75℃;
With 2-pyrazylcarboxylic acid; C16H10N4O4(4-)*2Cs(1+)*V2O4(2+)*4H2O; dihydrogen peroxide In acetonitrile at 50℃;
With tert.-butylhydroperoxide; cis-(Br,Br)-[Re(p-NC6H4CH3)Br2(4-MeO-quin-2-COO)(PPh3)]*MeOH; nitric acid In water at 60℃; for 2h; General procedure: The reactions of alcohols and hydrocarbons were usually carried out in air in thermostated Pyrex cylindrical vessels with vigorous stirring and using MeCN as solvent. Typically, catalyst and the co-catalyst (acid) were introduced into the reaction mixture in the form of stock solutions in acetonitrile. The substrate (alcohol or hydrocarbon) was then added and the reaction started when TBHP was introduced in one portion. (CAUTION. The combination of air or molecular oxygen and peroxides with organic compounds a televated temperatures may be explosive). The reactions with 1-phenylethanol were analyzed by 1H NMR method (solutions in acetone-d6; ‘‘Bruker AMX-400” instrument, 400 MHz). Areas of methylgroup signals were measured to quantify oxygenates formed in oxidations of 1-phenylethanol. Previously in our works the samples obtained in the alkane oxidation were typically analyzed twice(before and after their treatment with PPh3) by GC (LKhM-80-6 instrument, columns 2 m with 5% Carbowax 1500 on 0.25-0.315 mm Inerton AW-HMDS; carrier gas argon). This method(an excess of solid triphenylphosphine is added to the samples 10-15 min before the GC analysis) was proposed by one of us earlier[20]. In order to precisely determine concentrations of isomericalkanols the samples of reaction solutions after addition of nitromethane were analyzed only after reduction with PPh3. Attribution of peaks was made by comparison with chromatograms of authentic samples.
1: 12.8 %Chromat. 2: 11.7 %Chromat. 3: 7.7 %Chromat. With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride; iodosylbenzene In acetonitrile for 1h; Darkness; 2.2. Catalytic oxidation reactions General procedure: The following procedure was adopted to assess the oxidation of different substrates catalyzed by the previously prepared metalloporphyrins: about 1.0mg of the metalloporphyrin was weighed in a 2mL thermostatic glass reactor tube equipped with a magnetic stirrer. The reactor tube was placed inside a dark recipient, and iodosylbenzene was added, to obtain a 1:10 catalyst/oxidant molar ratio. The reactor was degassed with argon for 15min, which was followed by addition of the solvent (acetonitrile, 400μL) and about 100μL of the substrate ((Z)-cyclooctene, cyclohexane or heptanes - 1:1000 catalyst/substrate molar ratio). The oxidation reactions were carried out under magnetic stirring for 1h or 24h. (Z)-cyclooctene had been previously purified by column chromatography on an alumina micro column. The reactions were quenched by addition of sodium sulfite saturated solution (approximately 0.1mol/L), to eliminate excess PhIO. The reaction mixture was transferred to a volumetric flask, and aliquots were analyzed by gas chromatography after addition of the internal standard (a solution of 99.9% octan-1-ol in acetonitrile 1.0×10-2mol/L). When the catalyst used in the reaction was insoluble (FeP6, MnP6, and CuP6), the solid catalyst was washed several times with methanol and acetonitrile after the reaction, to extract any reaction products that might have adsorbed onto the solid. The washing solutions were added to the previously separated reaction supernatant, and the contents of these combined solutions were analyzed by gas chromatography, also using octan-1-ol as internal standard. The product yields were based on the amount of PhIO added to the reactions. The molar ratio 1:10 catalyst/oxidant was estimated based on molecular mass of MP including the insoluble solids catalysts. Control experiments were also carried out in the absence of MPx using the methodology described above.
1: 10.8 %Chromat. 2: 10.2 %Chromat. 3: 6.5 %Chromat. With iodosylbenzene; C72H28ClF16FeN4O8S4 In acetonitrile for 1h; Darkness; 2.2. Catalytic oxidation reactions General procedure: The following procedure was adopted to assess the oxidation of different substrates catalyzed by the previously prepared metalloporphyrins: about 1.0mg of the metalloporphyrin was weighed in a 2mL thermostatic glass reactor tube equipped with a magnetic stirrer. The reactor tube was placed inside a dark recipient, and iodosylbenzene was added, to obtain a 1:10 catalyst/oxidant molar ratio. The reactor was degassed with argon for 15min, which was followed by addition of the solvent (acetonitrile, 400μL) and about 100μL of the substrate ((Z)-cyclooctene, cyclohexane or heptanes - 1:1000 catalyst/substrate molar ratio). The oxidation reactions were carried out under magnetic stirring for 1h or 24h. (Z)-cyclooctene had been previously purified by column chromatography on an alumina micro column. The reactions were quenched by addition of sodium sulfite saturated solution (approximately 0.1mol/L), to eliminate excess PhIO. The reaction mixture was transferred to a volumetric flask, and aliquots were analyzed by gas chromatography after addition of the internal standard (a solution of 99.9% octan-1-ol in acetonitrile 1.0×10-2mol/L). When the catalyst used in the reaction was insoluble (FeP6, MnP6, and CuP6), the solid catalyst was washed several times with methanol and acetonitrile after the reaction, to extract any reaction products that might have adsorbed onto the solid. The washing solutions were added to the previously separated reaction supernatant, and the contents of these combined solutions were analyzed by gas chromatography, also using octan-1-ol as internal standard. The product yields were based on the amount of PhIO added to the reactions. The molar ratio 1:10 catalyst/oxidant was estimated based on molecular mass of MP including the insoluble solids catalysts. Control experiments were also carried out in the absence of MPx using the methodology described above.
With [Cu(H1.5(N-methyldiethanolamine))2]2(H2-pyromellitato); dihydrogen peroxide; trifluoroacetic acid In water; acetonitrile at 50℃; for 2h; regioselective reaction;

  • 10
  • [ 543-49-7 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
YieldReaction ConditionsOperation in experiment
With vinyl acetate; subtilisin In di-isopropyl ether at 10 - 40℃;
With (R,R)-1,2-diphenylethylenediamine In ethanol Title compound not separated from byproducts;
  • 11
  • [ 543-49-7 ]
  • [ 6033-24-5 ]
YieldReaction ConditionsOperation in experiment
racemate resolution via acylation with vinyl acetate catalysed by lipase B from Candida antarctica;
  • 12
  • [ 592-76-7 ]
  • [ 589-82-2 ]
  • [ 543-49-7 ]
  • [ 589-55-9 ]
  • [ 111-70-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-Heptene With rhodium(III) chloride; boron trifluoride-tetrahydrofuran complex In tetrahydrofuran at 24℃; for 2h; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; water at 24℃; Further stages.;
  • 13
  • [ 543-49-7 ]
  • [ 62643-56-5 ]
  • 2-heptyl 7-aminoheptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-Aminoheptanoic acid hydrochloride With thionyl chloride at 30 - 35℃; for 0.5h; Stage #2: 2-Heptanol In chloroform for 3h; Heating;
  • 14
  • [ 543-49-7 ]
  • [ 110-43-0 ]
  • [ 6033-24-5 ]
YieldReaction ConditionsOperation in experiment
With lyophilized cells of Rhodococcus ruber DSM 44541; acetone In phosphate buffer at 24℃; for 24h; Title compound not separated from byproducts.;
With lyophilized cells of Rhodococcus ruber DSM 44541; acetone In phosphate buffer at 24℃; for 24h;
99.9 % ee With Fusarium proliferatum mycelia In aq. phosphate buffer Microbiological reaction; Resolution of racemate; enantioselective reaction;
With recombinant alcohol dehydrogenase from Pichia pastoris GS115, fused to N-terminus with hexahistidine; recombinant NAD(P)H oxidase from Lactobacillus sanfranciscensis; nicotinamide adenine dinucleotide phosphate In aq. buffer at 25℃; for 19h; Resolution of racemate; Enzymatic reaction; enantiospecific reaction;

  • 15
  • [ 6033-24-5 ]
  • [ 543-49-7 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate; (2-aminoethyl)diphenylphosphane In toluene at 30℃; for 3h;
With [ruthenium(II)(chloride)(2-aminomethyl-6-tolylpyridine)(1,4-bis(diphenylphosphino)butane)]; potassium <i>tert</i>-butylate; isopropyl alcohol at 50℃; for 2h; Inert atmosphere;
  • 16
  • [ 142-82-5 ]
  • [ 589-82-2 ]
  • [ 543-49-7 ]
  • [ 111-70-6 ]
YieldReaction ConditionsOperation in experiment
With cytochrome P450 BM3 from Bacillus megaterium 77-9H mutation; oxygen; NADPH In phosphate buffer; ethanol at 25℃; for 12h; Title compound not separated from byproducts;
  • 17
  • [ 142-82-5 ]
  • [ 123-19-3 ]
  • [ 110-43-0 ]
  • [ 589-82-2 ]
  • [ 543-49-7 ]
  • [ 589-55-9 ]
  • [ 111-70-6 ]
  • [ 106-35-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: n-heptane With sodium metavanadate tetrahydrate; sulfuric acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 2h; Stage #2: With triphenylphosphine In water; acetonitrile
Stage #1: n-heptane With sodium metavanadate tetrahydrate; sulfuric acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 3h; Stage #2: With triphenylphosphine In water; acetonitrile
Stage #1: n-heptane With sodium metavanadate tetrahydrate; sulfuric acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 5h; Stage #2: With triphenylphosphine In water; acetonitrile
Stage #1: n-heptane With tert.-butylhydroperoxide; OCu4(N(CH2CH2O)3)4(BOH)4(2+)*2BF4(1-)=[OCu4(N(CH2CH2O)3)4(BOH)4][BF4]2 In water; acetonitrile at 50℃; for 5h; Stage #2: With triphenylphosphine regioselective reaction;

  • 18
  • [ 543-49-7 ]
  • [ 1073561-04-2 ]
  • [ 1193642-87-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-(tetrahydropyran-2-yloxymethyl)isophthalic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 2-Heptanol With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 40℃; for 40h; Inert atmosphere; Stage #3: With dmap In N,N-dimethyl-formamide at 40℃; for 1h; Inert atmosphere;
  • 19
  • [ 142-82-5 ]
  • [ 589-82-2 ]
  • [ 543-49-7 ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 45% With iodosylbenzene In acetonitrile at 25℃; for 24h; Inert atmosphere; regioselective reaction;
1: 15.2% 2: 15% With iodosylbenzene; 5,10,15,20-tetrakis(pentafluorophenyl)-1H,23H-porphyrin iron(III) chloride In dichloromethane; acetonitrile for 1h; Inert atmosphere;
1: 11% 2: 10% With iodosylbenzene In acetonitrile at 20℃; for 1h; Inert atmosphere;
1: 10% 2: 9% With iodosylbenzene In dichloromethane; acetonitrile for 1h; Inert atmosphere; regioselective reaction;
1: 9.9% 2: 9.5% With dihydrogen peroxide In acetonitrile at 50℃; for 50h;
1: 9.9% 2: 9.5% With Fe(mqmp)(CH3OH)Cl2; dihydrogen peroxide In acetonitrile at 50℃; for 24h;
1: 5 %Chromat. 2: 10 %Chromat. With iodosylbenzene In dichloromethane; acetonitrile at 20℃; for 1h; Inert atmosphere; 2.4. Oxidation of cyclooctene, cyclohexane, and n-heptane by PhIO catalyzed by FeMn-Hallo General procedure: The oxidation reactions were carried out in a thermostatic glassvessel (2.0 mL) equipped with a magnetic stirrer bar [6,8]. FeMn-Hallo (3.0 mg) and PhIO (0.22 mol) were suspended in the solvent(0.200 mL of dichloromethane/acetonitrile 1:1, v/v); the substrate(cyclooctene, cyclohexane, or n-heptane) was added to the reaction mixture, to give a constant metalloporphyrin/oxidant/substrate molar ratio of 1:20:2000. The oxidation reaction was allowed toproceed for 1 h, under magnetic stirring. At the end of this period,sodium sulfite was added to the reaction mixture, to quench there action and to eliminate excess PhIO. The reaction products were separated from FeMn-Hallo by centrifugation and transferred to a volumetric flask. Next, FeMn-Hallo was washed several times with methanol and acetonitrile, to extract any reaction product that might have been retained in the solid catalyst. The solution containing the final reaction products and the solvents from theFeMn-Hallo washing process were combined and analyzed by gas chromatography. Product yields were quantified on the basis of PhIO; high-purity n-octanol (99.9%) was the internal standard.
With cytochrome P450 BM-3 enzyme mutant 9-10A-F87A Enzymatic reaction; 3 Regiospecific Activity General procedure: Table 11 shows product distributions for hydroxylation of alkanes catalyzed by cytochrome P450 BM-3 variants wt F87A and 9-10A F87A.
With cytochrome P450 BM-3 enzyme mutant wt F87A Enzymatic reaction; 3 Regiospecific Activity General procedure: Table 11 shows product distributions for hydroxylation of alkanes catalyzed by cytochrome P450 BM-3 variants wt F87A and 9-10A F87A.
1: 6.5 %Chromat. 2: 5.6 %Chromat. With iodosylbenzene; C72H28F16N4O8S4(2-)*C2H3O2(1-)*Mn(3+) In acetonitrile for 1h; Darkness; 2.2. Catalytic oxidation reactions General procedure: The following procedure was adopted to assess the oxidation of different substrates catalyzed by the previously prepared metalloporphyrins: about 1.0mg of the metalloporphyrin was weighed in a 2mL thermostatic glass reactor tube equipped with a magnetic stirrer. The reactor tube was placed inside a dark recipient, and iodosylbenzene was added, to obtain a 1:10 catalyst/oxidant molar ratio. The reactor was degassed with argon for 15min, which was followed by addition of the solvent (acetonitrile, 400μL) and about 100μL of the substrate ((Z)-cyclooctene, cyclohexane or heptanes - 1:1000 catalyst/substrate molar ratio). The oxidation reactions were carried out under magnetic stirring for 1h or 24h. (Z)-cyclooctene had been previously purified by column chromatography on an alumina micro column. The reactions were quenched by addition of sodium sulfite saturated solution (approximately 0.1mol/L), to eliminate excess PhIO. The reaction mixture was transferred to a volumetric flask, and aliquots were analyzed by gas chromatography after addition of the internal standard (a solution of 99.9% octan-1-ol in acetonitrile 1.0×10-2mol/L). When the catalyst used in the reaction was insoluble (FeP6, MnP6, and CuP6), the solid catalyst was washed several times with methanol and acetonitrile after the reaction, to extract any reaction products that might have adsorbed onto the solid. The washing solutions were added to the previously separated reaction supernatant, and the contents of these combined solutions were analyzed by gas chromatography, also using octan-1-ol as internal standard. The product yields were based on the amount of PhIO added to the reactions. The molar ratio 1:10 catalyst/oxidant was estimated based on molecular mass of MP including the insoluble solids catalysts. Control experiments were also carried out in the absence of MPx using the methodology described above.

Reference: [1]Castro, Kelly A. D. F.; Westrup, Kátia C. M.; Silva, Sandrina; Pereira, Patrícia M. R.; Simões, Mário M. Q.; Neves, Maria da Graça P. M. S.; Cavaleiro, José A. S.; Tomé, João P. C.; Nakagaki, Shirley [European Journal of Inorganic Chemistry, 2021, vol. 2021, # 28, p. 2857 - 2869]
[2]Location in patent: experimental part Castro, Kelly Aparecida Dias De Freitas; Bail, Alesandro; Groszewicz, Pedro Braga; MacHado, Guilherme Sippel; Schreiner, Wido Herwig; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2010, vol. 386, # 1-2, p. 51 - 59]
[3]Location in patent: experimental part MacHado, Guilherme Sippel; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2012, vol. 413-414, p. 94 - 102]
[4]Location in patent: experimental part Castro, Kelly Aparecida Dias De Freitas; Bail, Alesandro; Groszewicz, Pedro Braga; MacHado, Guilherme Sippel; Schreiner, Wido Herwig; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2010, vol. 386, # 1-2, p. 51 - 59]
[5]Location in patent: experimental part Nayak, Sanjit; Gamez, Patrick; Kozlevčar, Bojan; Pevec, Andrej; Roubeau, Olivier; Dehnen, Stefanie; Reedijk, Jan [Polyhedron, 2010, vol. 29, # 10, p. 2291 - 2296]
[6]Location in patent: scheme or table Nayak, Sanjit; Gamez, Patrick; Kozlevčar, Bojan; Pevec, Andrej; Roubeau, Olivier; Dehnen, Stefanie; Reedijk, Jan [Polyhedron, 2010, vol. 29, # 10, p. 2291 - 2296]
[7]Machado, Guilherme Sippel; Ucoski, Geani Maria; Lima, Omar José De; Ciuffi, Kátia Jorge; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2013, vol. 460-461, p. 124 - 131]
[8]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - US2016/24482, 2016, A1 Location in patent: Paragraph 0341
[9]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - US2016/24482, 2016, A1 Location in patent: Paragraph 0341
[10]de F. Castro, Kelly A.D.; Simões, Mário M.Q.; da Graça P.M.S. Neves, Maria; Cavaleiro, José A.S.; Ribeiro, Ronny R.; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2015, vol. 503, p. 9 - 19]
  • 20
  • [ 543-49-7 ]
  • [ 124-07-2 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
  • [ 117636-67-6 ]
YieldReaction ConditionsOperation in experiment
1.57 g With Candida antarctica lipase B immobilized on acrylic resin catalyst In pentane at 20 - 25℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
  • 21
  • [ 543-49-7 ]
  • [ 64-19-7 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
  • R-2-heptanol acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.04 g With Candida antarctica lipase B immobilized on acrylic resin catalyst In pentane at 20 - 25℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
  • 22
  • [ 543-49-7 ]
  • [ 142-62-1 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
  • [ 117636-56-3 ]
YieldReaction ConditionsOperation in experiment
1.47 g With Candida antarctica lipase B immobilized on acrylic resin catalyst In pentane at 20 - 25℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
  • 23
  • [ 543-49-7 ]
  • [ 107-92-6 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
  • [ 117636-41-6 ]
  • [ 117636-45-0 ]
YieldReaction ConditionsOperation in experiment
With Candida cylindracea lipase catalyst In n-heptane at 20 - 25℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
With Penicillium roqueforti lipase catalyst In n-heptane at 20 - 25℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
  • 24
  • [ 543-49-7 ]
  • [ 107-92-6 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
  • [ 117636-45-0 ]
YieldReaction ConditionsOperation in experiment
1.27 g With Candida antarctica lipase B immobilized on acrylic resin catalyst In pentane at 20 - 25℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
  • 25
  • [ 543-49-7 ]
  • [ 110-43-0 ]
  • [ 589-82-2 ]
YieldReaction ConditionsOperation in experiment
With 1H-imidazole; dihydrogen peroxide In water; acetonitrile at 80℃; for 4h; chemoselective reaction;
  • 26
  • [ 64-17-5 ]
  • [ 67-64-1 ]
  • [ 71-36-3 ]
  • [ 23708-56-7 ]
  • [ 6032-29-7 ]
  • [ 543-49-7 ]
  • [ 5932-79-6 ]
YieldReaction ConditionsOperation in experiment
1: 10.3 %Chromat. 2: 42.9 %Chromat. 3: 6.5 %Chromat. 4: 10.7 %Chromat. Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate In toluene at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen In toluene at 110℃; 10 Example 10One-pot alkylation and hydrogenation using ABE-mix with various amounts of base, temperature, H2 gas to produce corresponding alcoholsD'F'[0254] 5% palladium on carbon (0.01 mmol), K3PO4 (mol varied according to the amounts in Table 9), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To each vessel, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to each vessel. Each vessel was sealed, and kept at 145°C in a pre-heated metal block. Each reaction mixture was stirred at 145°C over 20 hours.[0255] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (pressure as shown in Table 9). Each reaction mixture was stirred at one of the temperatures listed in Table 9 below for 14 hours, and then cooled to room temperature. Note that reactions 4, 8, and 12 were performed neat. GC analysis of each final reaction mixture yielded the ratio of ketones and A'-F' products in Table 9. FIG. 9 also depicts effect of varying the concentration of base used on the yield of ketones and alcohols.
1: 5.3 %Chromat. 2: 15.5 %Chromat. 3: 18.9 %Chromat. 4: 40.3 %Chromat. Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate In toluene at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen In toluene at 110℃; 10 Example 10One-pot alkylation and hydrogenation using ABE-mix with various amounts of base, temperature, H2 gas to produce corresponding alcoholsD'F'[0254] 5% palladium on carbon (0.01 mmol), K3PO4 (mol varied according to the amounts in Table 9), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To each vessel, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to each vessel. Each vessel was sealed, and kept at 145°C in a pre-heated metal block. Each reaction mixture was stirred at 145°C over 20 hours.[0255] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (pressure as shown in Table 9). Each reaction mixture was stirred at one of the temperatures listed in Table 9 below for 14 hours, and then cooled to room temperature. Note that reactions 4, 8, and 12 were performed neat. GC analysis of each final reaction mixture yielded the ratio of ketones and A'-F' products in Table 9. FIG. 9 also depicts effect of varying the concentration of base used on the yield of ketones and alcohols.
1: 5.6 %Chromat. 2: 20.1 %Chromat. 3: 10 %Chromat. 4: 21.5 %Chromat. Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate In toluene at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen In toluene at 110℃; 10 Example 10One-pot alkylation and hydrogenation using ABE-mix with various amounts of base, temperature, H2 gas to produce corresponding alcoholsD'F'[0254] 5% palladium on carbon (0.01 mmol), K3PO4 (mol varied according to the amounts in Table 9), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To each vessel, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to each vessel. Each vessel was sealed, and kept at 145°C in a pre-heated metal block. Each reaction mixture was stirred at 145°C over 20 hours.[0255] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (pressure as shown in Table 9). Each reaction mixture was stirred at one of the temperatures listed in Table 9 below for 14 hours, and then cooled to room temperature. Note that reactions 4, 8, and 12 were performed neat. GC analysis of each final reaction mixture yielded the ratio of ketones and A'-F' products in Table 9. FIG. 9 also depicts effect of varying the concentration of base used on the yield of ketones and alcohols.
  • 27
  • [ 64-17-5 ]
  • [ 67-64-1 ]
  • [ 71-36-3 ]
  • [ 23708-56-7 ]
  • [ 6032-29-7 ]
  • [ 543-49-7 ]
YieldReaction ConditionsOperation in experiment
1: 6.1 %Chromat. 2: 20.9 %Chromat. 3: 5.8% Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate In toluene at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen In toluene at 20℃; 10 Example 10One-pot alkylation and hydrogenation using ABE-mix with various amounts of base, temperature, H2 gas to produce corresponding alcoholsD'F'[0254] 5% palladium on carbon (0.01 mmol), K3PO4 (mol varied according to the amounts in Table 9), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To each vessel, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to each vessel. Each vessel was sealed, and kept at 145°C in a pre-heated metal block. Each reaction mixture was stirred at 145°C over 20 hours.[0255] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (pressure as shown in Table 9). Each reaction mixture was stirred at one of the temperatures listed in Table 9 below for 14 hours, and then cooled to room temperature. Note that reactions 4, 8, and 12 were performed neat. GC analysis of each final reaction mixture yielded the ratio of ketones and A'-F' products in Table 9. FIG. 9 also depicts effect of varying the concentration of base used on the yield of ketones and alcohols.
1: 6.1 %Chromat. 2: 26 %Chromat. 3: 6.3 %Chromat. Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate In toluene at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen In toluene at 110℃; 10 Example 10One-pot alkylation and hydrogenation using ABE-mix with various amounts of base, temperature, H2 gas to produce corresponding alcoholsD'F'[0254] 5% palladium on carbon (0.01 mmol), K3PO4 (mol varied according to the amounts in Table 9), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To each vessel, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to each vessel. Each vessel was sealed, and kept at 145°C in a pre-heated metal block. Each reaction mixture was stirred at 145°C over 20 hours.[0255] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (pressure as shown in Table 9). Each reaction mixture was stirred at one of the temperatures listed in Table 9 below for 14 hours, and then cooled to room temperature. Note that reactions 4, 8, and 12 were performed neat. GC analysis of each final reaction mixture yielded the ratio of ketones and A'-F' products in Table 9. FIG. 9 also depicts effect of varying the concentration of base used on the yield of ketones and alcohols.
  • 28
  • [ 64-17-5 ]
  • [ 67-64-1 ]
  • [ 71-36-3 ]
  • [ 23708-56-7 ]
  • [ 543-49-7 ]
  • [ 5932-79-6 ]
YieldReaction ConditionsOperation in experiment
1: 40 %Chromat. 2: 16 %Chromat. 3: 19 %Chromat. Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate In toluene at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen In toluene at 110℃; for 14h; 9 Example 9One-pot alkylation and hydrogenation using ABE-mixF'40% (<1 %)[0252] 5% palladium on carbon (0.01 mmol), K3PO4 (4.5 mmol), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To the tube, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to the tube. The tube was sealed, and kept at 145°C in a pre-heated metal block. The reaction mixture was stirred at 145°C over 20 hours. A sample of the reaction mixture was taken for GC analysis.[0253] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (150 psi). The reaction mixture was stirred at 110°C for 14 hours, and then cooled to room temperature. GC analysis of the reaction mixture yielded the ratio of A'-F' products as shown in the reaction scheme above. Yields were determined based on acetone. The yields in parentheses denote the corresponding yields of the ketones.
1: 17.3 %Chromat. 2: 12.8 %Chromat. 3: 10.8 %Chromat. Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate In toluene at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen In toluene at 20℃; 10 Example 10One-pot alkylation and hydrogenation using ABE-mix with various amounts of base, temperature, H2 gas to produce corresponding alcoholsD'F'[0254] 5% palladium on carbon (0.01 mmol), K3PO4 (mol varied according to the amounts in Table 9), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To each vessel, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to each vessel. Each vessel was sealed, and kept at 145°C in a pre-heated metal block. Each reaction mixture was stirred at 145°C over 20 hours.[0255] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (pressure as shown in Table 9). Each reaction mixture was stirred at one of the temperatures listed in Table 9 below for 14 hours, and then cooled to room temperature. Note that reactions 4, 8, and 12 were performed neat. GC analysis of each final reaction mixture yielded the ratio of ketones and A'-F' products in Table 9. FIG. 9 also depicts effect of varying the concentration of base used on the yield of ketones and alcohols.
1: 8.9 %Chromat. 2: 13.3 %Chromat. 3: 5.6 %Chromat. Stage #1: ethanol; acetone; butan-1-ol With potassium phosphate at 145℃; for 20h; Sealed tube; Stage #2: With hydrogen at 20℃; 10 Example 10One-pot alkylation and hydrogenation using ABE-mix with various amounts of base, temperature, H2 gas to produce corresponding alcoholsD'F'[0254] 5% palladium on carbon (0.01 mmol), K3PO4 (mol varied according to the amounts in Table 9), and a magnetic stir bar were added to a high-pressure reaction vessel (HEL parallel synthesizer). To each vessel, 1.5 mL of toluene was added. Then, acetone (2.3 mmol), ethanol (1 mmol), and butanol (3.7 mmol) were also added to each vessel. Each vessel was sealed, and kept at 145°C in a pre-heated metal block. Each reaction mixture was stirred at 145°C over 20 hours.[0255] To this reaction mixture, 5% platinum on carbon (0.02 mmol) was added, and the reaction vessel was pressurized with H2 gas (pressure as shown in Table 9). Each reaction mixture was stirred at one of the temperatures listed in Table 9 below for 14 hours, and then cooled to room temperature. Note that reactions 4, 8, and 12 were performed neat. GC analysis of each final reaction mixture yielded the ratio of ketones and A'-F' products in Table 9. FIG. 9 also depicts effect of varying the concentration of base used on the yield of ketones and alcohols.
  • 29
  • [ 520-45-6 ]
  • [ 123-19-3 ]
  • [ 52390-72-4 ]
  • [ 589-55-9 ]
YieldReaction ConditionsOperation in experiment
10.8%Chromat.; 5.7%Chromat.; 17.7%Chromat. With hydrogen; at 200 - 220℃; under 46544.6 - 56887.8 Torr; for 3.3h;Inert atmosphere; Sealed tube; In the stainless steel inset was put 3.20 g of 2% Ru-alumina catalyst (Afa-Aesar) and 0.51 g of DHAA and the inset was placed inside of the reactor. The reactor was sealed and purged with argon and hydrogen three times each and then hydrogen filled to a pressure of 1100 psi. Heating was started and temperature of the catalyst bed was maintained at 200-220 C for 3.3 hours. The pressure drop related to hydrogen consumption was observed and in the end of hydrogenation it was 900 psi. The reactor was cooled down, purged with argon, the inset was removed and the catalyst was washed with 5 mL of methyl acetate. The resulting wash was filtered and analyzed by GC/MS. GCMS qualitative analysis of products formed is shown in Table 15 and also presents a theoretical estimation of the calorific value of a mixture. 100% DHAA reacted. 41% was a mixture of higher alcohols and ketones of which 27.7% was higher alcohols and 23.4% of that was heptanols.
  • 30
  • [ 142-82-5 ]
  • [ 110-43-0 ]
  • [ 589-82-2 ]
  • [ 543-49-7 ]
  • [ 589-55-9 ]
  • [ 106-35-4 ]
YieldReaction ConditionsOperation in experiment
1: 22% 2: 25% 3: 13% 4: 15% 5: 17% With [PPh4]2[MnV(N)(CN)4]; dihydrogen peroxide; acetic acid In 2,2,2-trifluoroethanol at 23℃; for 5h; Inert atmosphere;
1: 11.5 %Chromat. 2: 10.3 %Chromat. 3: 6.2 %Chromat. With iodosylbenzene; C51H13ClF19FeN4O2S In acetonitrile for 1h; Darkness; 2.2. Catalytic oxidation reactions General procedure: The following procedure was adopted to assess the oxidation of different substrates catalyzed by the previously prepared metalloporphyrins: about 1.0mg of the metalloporphyrin was weighed in a 2mL thermostatic glass reactor tube equipped with a magnetic stirrer. The reactor tube was placed inside a dark recipient, and iodosylbenzene was added, to obtain a 1:10 catalyst/oxidant molar ratio. The reactor was degassed with argon for 15min, which was followed by addition of the solvent (acetonitrile, 400μL) and about 100μL of the substrate ((Z)-cyclooctene, cyclohexane or heptanes - 1:1000 catalyst/substrate molar ratio). The oxidation reactions were carried out under magnetic stirring for 1h or 24h. (Z)-cyclooctene had been previously purified by column chromatography on an alumina micro column. The reactions were quenched by addition of sodium sulfite saturated solution (approximately 0.1mol/L), to eliminate excess PhIO. The reaction mixture was transferred to a volumetric flask, and aliquots were analyzed by gas chromatography after addition of the internal standard (a solution of 99.9% octan-1-ol in acetonitrile 1.0×10-2mol/L). When the catalyst used in the reaction was insoluble (FeP6, MnP6, and CuP6), the solid catalyst was washed several times with methanol and acetonitrile after the reaction, to extract any reaction products that might have adsorbed onto the solid. The washing solutions were added to the previously separated reaction supernatant, and the contents of these combined solutions were analyzed by gas chromatography, also using octan-1-ol as internal standard. The product yields were based on the amount of PhIO added to the reactions. The molar ratio 1:10 catalyst/oxidant was estimated based on molecular mass of MP including the insoluble solids catalysts. Control experiments were also carried out in the absence of MPx using the methodology described above.
  • 31
  • [ 543-49-7 ]
  • [ 123-20-6 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
  • [ 117636-41-6 ]
  • [ 117636-45-0 ]
YieldReaction ConditionsOperation in experiment
84 % ee With Burkholderia cepacia lipase In hexane at 30℃; for 3h; Resolution of racemate; enantioselective reaction;
  • 32
  • [ 108-05-4 ]
  • [ 543-49-7 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
  • (S)-2-heptyl acetate [ No CAS ]
  • R-2-heptanol acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 47 % ee 2: 46 % ee With immobilized LipG9 In hexane at 35℃; for 24h; Resolution of racemate; Enzymatic reaction; 2.5 General procedure for enzymatic kinetic resolution by transesterification reactions General procedure: To a solution of appropriated alcohol 1a-6a (0.1mmol) in n-hexane (2mL), vinyl acetate (34mg, 0.4mmol) and 50mg (corresponding to 11U of activity) of immobilized enzyme (LipG9) were added and the was reaction carried out at controlled temperature and 150rpm. The progress of the reaction was monitored by GC chiral analysis.
  • 33
  • [ 543-49-7 ]
  • [ 110-43-0 ]
  • [ 6033-23-4 ]
  • [ 6033-24-5 ]
YieldReaction ConditionsOperation in experiment
With NADP In acetone at 50℃; for 22h; Resolution of racemate;
  • 34
  • [ 543-49-7 ]
  • [ 13338-63-1 ]
  • C18H25NO3 [ No CAS ]
  • 35
  • [ 142-82-5 ]
  • [ 110-43-0 ]
  • [ 96-04-8 ]
  • [ 543-49-7 ]
YieldReaction ConditionsOperation in experiment
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; manganese (II) acetate tetrahydrate; ozone at 95℃; for 4h; 13 Example 1 General procedure: A thermometer and cooling condenser were attached to a 50 mL glass four-necked flask. Tetradecane (manufactured by Tokyo Chemical Industry Co., Ltd., 15 g, 75.6 mmol), 2,2,6,6-tetramethylpiperidine-1-oxyl (hereinafter sometimes referred to as "TEMPO"Wako Pure Chemical Industries, Ltd.,0.30 g, 1.9 mmol, 2.5 mol% of the substrate), manganese acetate tetrahydrate (manufactured by Wako Pure Chemical Industries, 0.0050 g, 0.019 mmol, 0.025 mol% of the substrate) was charged After that, the container was immersed in a water bath and the temperature was raised until the liquid temperature reached 95 ° C. Cobalt naphthenate (manufactured by Wako Pure Chemical Industries, Ltd., cobalt content: 6.0% by weight, 0.37 g, 0.38 mmol, 0.5 mol% of the substrate) was added and an ozone generator (Wintec Industrial Co., (Oxygen content: 20.7% by volume, ozone gas content: 0.8% by volume) containing ozone gas generated by using a flow rate of 100 mL / min (1 with respect to 1 mol of the substrate) 32 L / min.) While intermittently feeding with bubbling.After 4 hours, the conversion (substrate conversion) of tetradecane was measured using gas chromatography (column: 007-FFAP, manufactured by Tokyo Chemical Industry Co., Ltd.) and found to be 11%.As reaction products (oxides), tetradecanol, tetradecanone, tetradecadione were obtained.
  • 36
  • [ 543-49-7 ]
  • [ 111-55-7 ]
  • R-2-heptanol acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Candida antarctica lipase B immobilized on a macroporous acrylic resin at 40℃; for 20h; Green chemistry; Enzymatic reaction; General experiment for the optimised acetylation of alcohols, according to Scheme 2: General procedure: Lipozyme 435 (2% wt) was added to a solution of an alcohol (1 equiv) in EGDA (2 equiv).The reaction mixture was incubated in an orbital shaker (40 °C, 150 rpm) and the reaction progress wasmonitored by GC-FID (see Table 1).
  • 37
  • [ 142-82-5 ]
  • [ 123-19-3 ]
  • [ 110-43-0 ]
  • [ 589-82-2 ]
  • [ 543-49-7 ]
  • [ 106-35-4 ]
YieldReaction ConditionsOperation in experiment
1: 7% 2: 8% 3: 14% 4: 11% 5: 6% With iodosylbenzene In chloroform; acetonitrile at 0.26℃; for 1.5h; Darkness; regioselective reaction;
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