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Organic Building Blocks
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Decan-2-one
Chemistry
Organic Building Blocks
Ketones
Aliphatic Chain Hydrocarbons

[ CAS No. 693-54-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
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Chemical Structure| 693-54-9
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Quality Control of [ 693-54-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 693-54-9 ]

Product Details of [ 693-54-9 ]

CAS No. :693-54-9 MDL No. :MFCD00009571
Formula : C10H20O Boiling Point : -
Linear Structure Formula :- InChI Key :ZAJNGDIORYACQU-UHFFFAOYSA-N
M.W : 156.27 Pubchem ID :12741
Synonyms :

Calculated chemistry of [ 693-54-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 7
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.38
TPSA : 17.07 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) : -4.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 3.73
Log Po/w (WLOGP) : 3.33
Log Po/w (MLOGP) : 2.7
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 3.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.314 mg/ml ; 0.00201 mol/l
Class : Soluble
Log S (Ali) : -3.78
Solubility : 0.0259 mg/ml ; 0.000166 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.0591 mg/ml ; 0.000378 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.62

Safety of [ 693-54-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 693-54-9 ]

* 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 [ 693-54-9 ]

[ 693-54-9 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 872-05-9 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
95% With chromium(VI) oxide; palladium dichloride; In water; acetonitrile; at 20 - 60℃; for 6.5h; General procedure: To a stirred solution of olefin (0.4mmol) in CH3CN (3.5mL) and H2O (0.5mL) were added PdCl2 (3.6mg, 0.02mmol, 5mol%) and CrO3 (20mg, 0.6mmol, 0.5equiv) at room temperature. The reaction mixture was warmed to 60C and stirred for specified time (see Tables 5-7) in a closed flask. The reaction mixture was then filtered through a small pad of silica gel and washed with EtOAc and the filtrate concentrated. The residue in some cases contained virtually pure compound and no further purification was necessary. In other cases the residue was purified by silica gel column chromatography using petroleum ether/EtOAc as an eluent to afford the methyl ketones.
86% With tert.-butylhydroperoxide;silver(I) hexafluorophosphate; [Pd(Quinox)Cl2]; In dichloromethane; water; at 0 - 20℃; for 0.333333h;Protection from light;Product distribution / selectivity; General TBHP Mediated Wacker Reaction:Table 1 reports individual examples while the following description provides a common reaction scheme used in each example with deviations noted. In the dark, AgSbF6 (51.5 mg, 0.15 mmol), Pd(quinox)Cl2 complex (22.5 mg, 0.06 mmol), and a magnetic stir bar were added to a 100 mL round bottomed flask. DCM (4.8 mL) was added to the flask and the mixture was stirred for 15 min. The mixture was then diluted with DCM (20 mL) and 70 wt % TBHP(aq) (5.2 mL, 36 mmol) was added. The resulting mixture was stirred for an additional 10 min, before being cooled in an ice bath. Once the solution had cooled, the substrate (3.0 mmol) was added with stirring. After 5 min, the ice bath was removed and the reaction mixture was allowed to slowly warm to room temperature. Once TLC indicated complete consumption of starting material, the reaction was quenched with a saturated aqueous solution of Na2SO3 (50 mL) to consume excess TBHP. The mixture was transferred to a separatory funnel and diluted with hexanes (50 mL). The aqueous layer was separated and back extracted with hexanes (25 mL). The combined organics were washed with water (4×25 mL) and brine (50 mL). The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel flash chromatography if necessary; the product containing fractions were combined and concentrated under reduced pressure. The general reaction scheme was as follows:; Several common protecting groups for allylic alcohols were shown to be compatible with these conditions, providing the methyl ketone products in high yields (Table 1, entries 1-4). No aldehyde product was detected in any of these cases by GC or 1H NMR analysis. Thus, the above approach can be substantially free or completely free of undesired aldehyde products. Additionally, silyl protected allylic alcohols proceed to product at a significantly faster rate, allowing for the use of lower catalyst loadings (entry 2). An acetal-protecting group, was stable to Lewis acidic, aqueous reaction conditions (entry 3). A homoallylic alcohol also was converted to the methyl ketone in excellent yield (entry 5).The corresponding ketones were each confirmed using NMR, IR and HRMS analyses. The 2-oxooctan-3-yl acetate, 3-(tert-butyldimethylsiloxy)octan-2-one, 3-(ethoxymethoxy)octan-2-one, 1-cyclohexyl-2-oxopropyl acetate, 4-(tert-butyldimethylsolxy)-4-phenylbutan-2-one, 2-decanone, methyl 10-oxoundecanoate, 6-(2,2-dimethyl-1,3-dioxolan-4-yl)hexan-2-one, 11-chloroundecan-2-one, 1-p-tolyethanone were recovered as colorless oils. The 11-hydroxyundecan-2-one, tert-butyl 4-acetylphenylcarbamate, and 1-(3-nitro)ethanone were recovered as a white solid having a melting point of 39-40 C., 113-114 C., and 68-70 C., respectively. Similarly, 11-hydroxyundecan-2-one was isolated as a white solid.The catalytic system was further evaluated to determine whether it was a general catalyst for the Wacker oxidation. Excitingly, the current system rapidly consumes decene leading to 2-decanone in good yield with no appreciable amounts of internal isomers (entry 6). Lowering the amount of TBHP led to conversion of decene without significant loss of yield or increase in isomerization (entry 7). Other functional groups were evaluated including an alkene with a free distal alcohol, which was used to demonstrate the scalability of the reaction using a reduced catalyst loading (entries 8 and 9). Additionally, alkenes containing common functional groups including a methyl ester, acetonide, and primary chloride are well tolerated (entries 10-12). A number of styrene derivatives, another challenging substrate class for the Tsuji-Wacker oxidation, were also evaluated. Substituted styrenes with various functional groups were efficiently oxidized, although a highly electron-deficient system led to a lower yield and a trace amount of m-nitro benzaldehyde (entries 13-15). It should be noted that these reactions are exothermic; therefore the oxidations were initiated at 0 C.
With copper(II) choride dihydrate; hydrogen; oxygen; In N,N-dimethyl acetamide; water; at 80℃; under 760.051 Torr; A DMA solution containing 1.0 mmol of 1 -decene is prepared, and 0.05 mmol of a Pd catalyst, (0.15 mm of) copper (II) chloride dihydrate, and a small amount of H2 are added thereto to make a suspension and to be stirred in an oxygen gas atmosphere at 1 atmospheric pressure for several hours. The catalyst is then removed from the suspension by filtration. Subsequently, the filtrate is concentrated for purification by column chromatography to obtain 2-decanone as an oxidation product.
Reference： [1]Tetrahedron,2014,vol. 70,p. 4760 - 4767
[2]Journal of Organic Chemistry,2014,vol. 79,p. 5787 - 5793
[3]Tetrahedron Letters,1988,vol. 29,p. 2885 - 2888
[4]Journal of the American Chemical Society,2009,vol. 131,p. 4 - 5
[5]Chemistry Letters,2003,vol. 32,p. 180 - 181
[6]Tetrahedron Letters,2006,vol. 47,p. 1425 - 1428
[7]Tetrahedron Letters,1998,vol. 39,p. 8765 - 8768
[8]Patent: US2011/54176,2011,A1 .Location in patent: Page/Page column 9-10
[9]Angewandte Chemie - International Edition,2006,vol. 45,p. 481 - 485
[10]Tetrahedron Letters,1998,vol. 39,p. 6667 - 6670
[11]Tetrahedron Letters,2002,vol. 43,p. 8887 - 8891
[12]Green Chemistry,2014,vol. 16,p. 69 - 72
[13]Journal of the American Chemical Society,2007,vol. 129,p. 2246 - 2247
[14]Green Chemistry,2009,vol. 11,p. 1317 - 1320
[15]Journal of Organic Chemistry,2016,vol. 81,p. 2113 - 2121
[16]Chemistry Letters,1986,p. 2083 - 2084
[17]Journal of the American Chemical Society,1990,vol. 112,p. 5160 - 5166
[18]Tetrahedron Letters,1988,vol. 29,p. 2885 - 2888
[19]Journal of the American Chemical Society,1990,vol. 112,p. 5160 - 5166
[20]Tetrahedron Letters,1988,vol. 29,p. 2885 - 2888
[21]Organic Syntheses,1984,vol. 62,p. 9 - 9
[22]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1987,vol. 36,p. 99 - 103
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1987,p. 114 - 118
[23]ChemSusChem,2017,vol. 10,p. 3482 - 3489
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[25]Tetrahedron Letters,1983,vol. 24,p. 5159 - 5162
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[27]Journal of the Chemical Society. Chemical communications,1991,p. 1559 - 1560
[28]Journal of Organic Chemistry,1987,vol. 52,p. 1758 - 1764
[29]Tetrahedron Letters,1987,vol. 28,p. 3683 - 3686
[30]Canadian Journal of Chemistry,1992,vol. 70,p. 2485 - 2490
[31]Journal of Organometallic Chemistry,1987,vol. 334,p. C5 - C8
[32]Tetrahedron Letters,1995,vol. 36,p. 5925 - 5928
[33]Angewandte Chemie,1959,vol. 71,p. 176,180,182
    Angewandte Chemie,1962,vol. 74,p. 93
[34]Tetrahedron Letters,1987,vol. 28,p. 3683 - 3686
[35]Journal of Organic Chemistry,1980,vol. 45,p. 5387 - 5390
[36]Canadian Journal of Chemistry,1992,vol. 70,p. 2485 - 2490
[37]Journal of the Chemical Society. Chemical communications,1986,p. 909 - 910
[38]Journal of Organometallic Chemistry,1987,vol. 334,p. C5 - C8
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[40]Journal of Organometallic Chemistry,1998,vol. 551,p. 387 - 389
[41]Petroleum Chemistry,2002,vol. 42,p. 184 - 186
[42]Petroleum Chemistry,2003,vol. 43,p. 273 - 277
[43]Organic Letters,2006,vol. 8,p. 4117 - 4120
[44]Angewandte Chemie - International Edition,2006,vol. 45,p. 481 - 485
[45]Advanced Synthesis and Catalysis,2004,vol. 346,p. 849 - 854
[46]Chemical Communications,2002,p. 876 - 877
[47]Journal of the American Chemical Society,2009,vol. 131,p. 4 - 5
[48]Russian Chemical Bulletin,2008,vol. 57,p. 780 - 792
[49]Journal of the American Chemical Society,2009,vol. 131,p. 6076 - 6077
[50]Journal of the American Chemical Society,2010,vol. 132,p. 11872 - 11874
[51]Journal of Materials Chemistry,2011,vol. 21,p. 4768 - 4770
[52]RSC Advances,2013,vol. 3,p. 16296 - 16299
[53]Green Chemistry,2015,vol. 17,p. 2750 - 2757
[54]Patent: US2017/283343,2017,A1 .Location in patent: Paragraph 0227
  • 2
  • [ 693-54-9 ]
  • [ 1120-06-5 ]
YieldReaction ConditionsOperation in experiment
98% With Cp2Ti(BH4) In 1,2-dimethoxyethane for 0.0833333h;
98% With C31H35Cl2IrN2O2; potassium <i>tert</i>-butylate; isopropyl alcohol at 82℃; for 24h; Inert atmosphere; Schlenk technique; General procedure for hydrogen transformation. General procedure: Ketone(1.0 mmol) or imine (1.0 mmol), tBuOK (0.1 mmol) and cata-lyst (0.01 mmol) were weighed into an oven-dried Schlenk flask.Dry iPrOH (3.0 mL) was added to the flask, and the mixture was refluxed for the time specified under nitrogen. The reaction wascooled, and an aliquot was filtered through a pad of Celite andthe crude product was purified by column chromatography using petroleum ether and ethyl acetate. The analytical data of all products are consistent with the data reported in literature [2,3].
92% With C28H31ClN3Ru(1+)*F6P(1-); potassium <i>tert</i>-butylate; isopropyl alcohol at 82℃; for 17h; Inert atmosphere; Green chemistry;
64% Stage #1: Decan-2-one With polymethylhydrosiloxane; P(MeNCH2CH2)3N In tetrahydrofuran at 20℃; for 12h; Stage #2: In tetrahydrofuran at 20℃; for 1h;
With lithium aluminium tetrahydride
With sodium amalgam; ethanol inactive form of decanol-(2);
With hydrogen at 150℃;
100 % Chromat. With zirconium(IV) oxide In isopropyl alcohol for 5h; Heating;
With lithium aluminium tetrahydride
With potassium phosphate buffer; pig testicular 20β-hydroxysteroid dehydrogenase; NADPH at 37℃;
With water; hydrogen at 160℃; for 72h;
With 5% activated charcoal-supported ruthenium catalyst; hydrogen In water at 50℃; for 3h;
With sodium hydroxide; isopropyl alcohol for 0.333333h; Heating / reflux; 5 Examole 5: catalytic reduction of linear and cyclic dialkvl ketones, alkylaryl ketonesand diaryl ketones in presence of complex 8; Complex 8 (3.0 mg, 0.005 mmol) is suspended in 3 ml of 2-propanol in a 10mltailed tubes (Schlenk) and 2 ml of a 0.1M solution of NaOH in 2-propanol added.The complex is completely solubilised in a few minutes by stirring.Separately, in a 50ml tailed tubes (Schlenk), the necessary amount ofacetophenone (240 ul, 2 mmol) is dissolved in 19 ml of 2-propanol, the system isrefluxed and 1 ml of the previously prepared catalyst solution added (the addition of the complex is considered to be the starting time of the reaction). The molarratios between acetophenone/catalyst/NaOH are 2000/1/40; the reaction ismonitored at 1, 2, 5 minutes by collecting 0.5 ml of the solution and adding 4.5 mlof diethyl ether. This solution is passed through a silica column in order toeliminate the catalyst and sodium hydroxide, and finally analysed by gaschromatography. The gas chromatograph analysis data are reported in table 2.
With trans-[OsCl2(dppf)(en)]; hydrogen; sodium ethanolate In ethanol at 60℃; for 1h;
With C42H38ClN2OsP2; potassium <i>tert</i>-butylate; hydrogen In methanol at 70℃; for 0.5h; chemoselective reaction;
With C59H71ClFeN2O2P2Ru; sodium isopropylate; isopropyl alcohol at 60℃; for 2h; Inert atmosphere;
With chlorobenzene In methanol for 6h; Sealed tube; Green chemistry; chemoselective reaction;
93.5 %Chromat. With porous zirconium-phytic acid hybrid In isopropyl alcohol at 150℃; for 10h;
With pentamethylcyclopentadienyl(iridium(N-(2-(pyridin-2-yl)ethyl)methanesulfonamide))chloride In isopropyl alcohol at 85℃; for 3h;
With sodium tetrahydroborate
With trans-[OsCl2(dppf)(ethylenediamine)]; hydrogen; sodium ethanolate In ethanol at 60℃; for 1h; Schlenk technique;
57 %Spectr. With formic acid; [(η(6)-p-cymene)RuCl2]2(μ-1,1'-bis(diphenylphosphino)ferrocene); tetrabutylammomium bromide; triethylamine at 60℃; for 16h; 4.1 General procedure for the catalytic TH of carbonyl compounds and imines General procedure: The selected substrate (0.2-1.0mmol, 1 eq), [RuCl2(p-cymene)}2-μ-dppf] (6) (0.002-0.01mmol, 0,01-0,05 eq, 2.3-58.3mg), NEt3 (1.4-8.6mmol, 0.2-1.2mL) and CPME (0.5-1.5mL) were transferred into a 4mL vial. The mixture was heated at the selected temperature (40-80°C) under stirring for ca. 15min and finally the DES-5 (0.45-1.7mL) was added. After the addition of the DES, the vial was put into the oil bath and the Teflon cap pierced with a needle to help the emission of the CO2 produced. The reaction was then leaved to react at the selected temperature from 2 to 24h, depending on the substrate. The reaction mixture was worked taken up with water (1.5mL) and extracted with diethyl ether (4×1.5mL), then the combined organic layers washed with brine (1.5mL). The organic phase was then separated, dried over Na2SO4 and filtered. The solvent was removed and the crude was analysed by 1H and, when pure products were afforded, by 13C NMR spectroscopy.

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[18]Song, Jinliang; Zhou, Baowen; Zhou, Huacong; Wu, Lingqiao; Meng, Qinglei; Liu, Zhimin; Han, Buxing [Angewandte Chemie - International Edition, 2015, vol. 54, # 32, p. 9399 - 9403][Angew. Chem., 2015, vol. 127, p. 9531 - 9535,5]
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[20]Olivo, Giorgio; Giosia, Simone; Barbieri, Alessia; Lanzalunga, Osvaldo; Di Stefano, Stefano [Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10630 - 10635]
[21]Barbato, Cinzia; Baldino, Salvatore; Ballico, Maurizio; Figliolia, Rosario; Magnolia, Santo; Siega, Katia; Herdtweck, Eberhardt; Strazzolini, Paolo; Chelucci, Giorgio; Baratta, Walter [Organometallics, 2018, vol. 37, # 1, p. 65 - 77]
[22]Cavallo, Marzia; Arnodo, Davide; Mannu, Alberto; Blangetti, Marco; Prandi, Cristina; Baratta, Walter; Baldino, Salvatore [Tetrahedron, 2021, vol. 83]
  • 3
  • [ 2404-44-6 ]
  • [ 1120-06-5 ]
  • [ 872-05-9 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
92 % Chromat. With samarium diiodide; <i>tert</i>-butyl alcohol In tetrahydrofuran for 48h; Ambient temperature; Title compound not separated from byproducts;
Reference： [1]Girard, P.; Namy, J. L.; Kagan, H. B. [Journal of the American Chemical Society, 1980, vol. 102, # 8, p. 2693 - 2698]
  • 4
  • [ 764-93-2 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
82% With water; at 59.84℃; for 24.0h;Ionic liquid; Hydration Reaction-In a typical procedure, a solution of phenyl acetylene (1.0 mmol) was mixed with water (3.0 mmol) and BAILs (1.0 mmol). The reaction mixture was stirred for 10 h at 333 K. The reaction mixture was then diluted with H2O and extracted with chloroform and dried over anhydrous Na2SO4. The reaction mixture was analyzed using gas chromatography (Yonglin 6100; BP-5; 30 m × 0.25 mm × 0.25 mum). The products were identified by GC-MS (Shimadzu QP-5000; 30 m long, 0.25 mm i.d., with a 0.25-mum-thick capillary column, DB-1) and authentic samples obtained from Aldrich.Aqueous portion of the reaction mixture was evaporated to remove the water. Residue was washed three-four times with diethyl ether to remove any organic impurity. Finally, ionic liquid portion was dried under vacuum at 353 K for 4 h. The recovered ionic liquid was used in the recycling experiments.
78% With water; In neat (no solvent); at 100℃; for 24.0h;Green chemistry; General procedure: Reactions were performed in a magnetically stirred round bot-tomed flask fitted with a condenser and placed in a temperature controlled oil bath. Zeolite (H) (100 mg) was added to the well stirred solution of alkyne (2 mmol) and H2O (8 mmol) and the reac-tion mixture was allowed to stir at 100 C. After disappearance of the alkyne (monitored by TLC) or after an appropriate time, the reaction mixture was cooled to room temperature, diluted with ethyl acetate. The catalyst was separated by filtration and the removal of solvent in vacuo yielded residue. and it was further puri-fied by column chromatography using silica gel (100-200 mesh) to afford pure products. All the products were identified on the basisof H1 and C13NMR spectral data.
78% With Perfluorooctanesulfonic acid; C8AgF17O3S*H2O; In water; at 100℃; for 8.0h;Darkness; General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 mol%) and perfluorooctane sulfonateacid (2 mol%) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample.
37%Chromat. With sulfuric acid; C18H15CoN2O10S2(2-)*2Na(1+); water; In methanol; at 80℃; for 20.0h;Schlenk technique; General procedure: The 10 mL schlenk tube was charged with phenylacetylene (0.5 mmol, 51 mg), methanol (0.625 mL), catalyst (10 mumol, 2.0%), and then H2SO4 (10 mumol, 2.0%) dissolved in H2O (2.2mmol, 0.04 mL). The mixture was heated to 80 C and at it for 20 h in a closed tube with a magnetic stirring bar. The progres sof the reaction was monitored using TLC and GC-MS. After the reaction, the mixture was cooled to room temperature, and CH2Cl2 (5 mL) and water (5 mL) were added to the mixture.The aqueous and organic layers were separated, and the aqueous phase was extracted with CH2Cl2 (5 mL 3). The combined organic extracts were washed with a saturated NaCl solution,dried over Na2SO4, and concentrated under reduced pressure. Then the product acetophenone was obtained.

Reference： [1]Green Chemistry,2015,vol. 17,p. 532 - 537
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[3]Journal of the American Chemical Society,2013,vol. 135,p. 50 - 53
[4]Journal of the American Chemical Society,2011,vol. 133,p. 11632 - 11640
[5]Journal of Molecular Catalysis A: Chemical,2011,vol. 336,p. 1 - 7
[6]Tetrahedron Letters,2010,vol. 51,p. 4281 - 4283
[7]Synlett,2005,p. 3091 - 3094
[8]Chemistry - A European Journal,2011,vol. 17,p. 1261 - 1267
[9]Chemical Communications,2012,vol. 48,p. 434 - 436
[10]Tetrahedron Letters,2012,vol. 53,p. 3245 - 3249
[11]European Journal of Organic Chemistry,2019,vol. 2019,p. 5540 - 5548
[12]Applied Catalysis A: General,2015,vol. 505,p. 213 - 216
[13]Journal of Organometallic Chemistry,2015,vol. 799-800,p. 122 - 127
[14]Catalysis science and technology,2016,vol. 6,p. 7029 - 7032
[15]Organic Letters,2016,vol. 18,p. 2184 - 2187
[16]ChemCatChem,2014,vol. 6,p. 1612 - 1616
[17]Journal of Organic Chemistry,1982,vol. 47,p. 3331 - 3333
[18]Angewandte Chemie - International Edition,2010,vol. 49,p. 6813 - 6816
[19]Green Chemistry,2012,vol. 14,p. 1507 - 1514
[20]Chemical Communications,2015,vol. 51,p. 11896 - 11898
[21]Chinese Journal of Catalysis,2014,vol. 35,p. 1695 - 1700
[22]Angewandte Chemie - International Edition,2016,vol. 55,p. 13739 - 13743
    Angew. Chem.,2016,vol. 128,p. 13943 - 13947,5
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  • [ 693-54-9 ]
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[2]Tetrahedron Letters,1981,vol. 22,p. 4889 - 4890
[3]Chemistry Letters,1993,p. 571 - 572
[4]Synthesis,1999,p. 939 - 942
[5]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2857 - 2859
[6]Tetrahedron,2016,vol. 72,p. 7633 - 7637
[7]Tetrahedron,2002,vol. 58,p. 9879 - 9887
[8]Organic Process Research and Development,1998,vol. 2,p. 261 - 269
[9]Chemical Communications,2002,p. 3034 - 3035
[10]Journal of Organic Chemistry,2005,vol. 70,p. 3343 - 3352
[11]Organic Letters,2010,vol. 12,p. 4540 - 4543
[12]ChemCatChem,2014,vol. 6,p. 2419 - 2424
[13]Advanced Synthesis and Catalysis,2015,vol. 357,p. 51 - 58
[14]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 1943 - 1946
[15]Angewandte Chemie - International Edition,2003,vol. 42,p. 3810 - 3813
[16]Tetrahedron,2004,vol. 60,p. 1065 - 1072
[17]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 1943 - 1946
[18]Tetrahedron Letters,2001,vol. 42,p. 13 - 16
[19]Canadian Journal of Chemistry,2005,vol. 83,p. 702 - 710
[20]Russian Chemical Bulletin,2008,vol. 57,p. 2328 - 2331
[21]Chemistry Letters,1983,p. 379 - 380
[22]Synthetic Communications,1999,vol. 29,p. 163 - 166
[23]European Journal of Organic Chemistry,2010,p. 1971 - 1976
[24]Tetrahedron,2002,vol. 58,p. 3985 - 3991
[25]Journal of Organic Chemistry,2002,vol. 67,p. 1657 - 1662
[26]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2004,vol. 43,p. 936 - 946
[27]Physical Chemistry Chemical Physics,2010,vol. 12,p. 1741 - 1749
[28]RSC Advances,2015,vol. 5,p. 2647 - 2654
[29]Heterocycles,2010,vol. 81,p. 2539 - 2553
[30]Green Chemistry,2010,vol. 12,p. 1180 - 1186
[31]Tetrahedron,2017,vol. 73,p. 6052 - 6056
[32]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 99 - 100
[33]Catalysis Communications,2010,vol. 11,p. 1181 - 1184
[34]ACS Catalysis,2018,vol. 8,p. 5425 - 5430
[35]Chemistry Letters,2007,vol. 36,p. 212 - 213
[36]Chemical Communications,2009,p. 5159 - 5161
[37]Synthetic Communications,1999,vol. 29,p. 2105 - 2114
[38]Green Chemistry,2010,vol. 12,p. 310 - 315
[39]Organic and Biomolecular Chemistry,2016,vol. 14,p. 10630 - 10635
[40]Chemical Communications,2013,vol. 49,p. 5889 - 5891
[41]Agricultural and Biological Chemistry,1989,vol. 53,p. 2673 - 2677
[42]Chemistry Letters,1989,p. 519 - 522
[43]Journal of the Chemical Society. Perkin transactions II,1988,p. 533 - 536
[44]Agricultural and Biological Chemistry,1986,vol. 50,p. 1533 - 1538
[45]Russian Chemical Bulletin,2002,vol. 51,p. 982 - 985
[46]Tetrahedron Letters,2003,vol. 44,p. 1507 - 1509
[47]Tetrahedron,2003,vol. 59,p. 4997 - 5002
[48]Journal of the American Chemical Society,2004,vol. 126,p. 9724 - 9734
[49]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2005,vol. 44,p. 144 - 147
[50]Journal of Catalysis,2005,vol. 231,p. 41 - 47
[51]Journal of Organic Chemistry,2007,vol. 72,p. 2143 - 2150
[52]Organic Letters,2008,vol. 10,p. 2155 - 2158
[53]Tetrahedron Letters,2009,vol. 50,p. 3432 - 3435
[54]Advanced Synthesis and Catalysis,2010,vol. 352,p. 293 - 298
[55]Patent: WO2012/144650,2012,A1 .Location in patent: Page/Page column 46-48
[56]ChemCatChem,2013,vol. 5,p. 307 - 312
[57]Chemistry - A European Journal,2012,vol. 18,p. 16947 - 16954
[58]Chemistry - A European Journal,2013,vol. 19,p. 9452 - 9456
[59]ChemCatChem,2013,vol. 5,p. 2991 - 2999
[60]Journal of Chemical Sciences,2013,vol. 125,p. 1375 - 1383
[61]Synlett,2015,vol. 26,p. 1179 - 1184
[62]Chemical Communications,2018,vol. 54,p. 10164 - 10167
[63]RSC Advances,2019,vol. 9,p. 24259 - 24266
[64]European Journal of Organic Chemistry,2020,vol. 2020,p. 1579 - 1585
  • 6
  • [ 872-05-9 ]
  • [ 124-18-5 ]
  • [ 1120-06-5 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
1: 13% 2: 2% 3: 81% With oxygen; isopropyl alcohol at 75℃; for 15h;
1: 81% 2: 13% 3: 2% With oxygen; isopropyl alcohol at 75℃; for 15h; comparison of yields for oxidation-reduction hydration, catalyzed by variuos Co(II)complexes;
1: 52% 2: 12% 3: 32% With oxygen; isopropyl alcohol at 75℃; for 2h;
1: 45 % Chromat. 2: 7 % Chromat. 3: 22 % Chromat. With oxygen In isopropyl alcohol at 75℃; for 1h;
1: 45 % Chromat. 2: 7 % Chromat. 3: 22 % Chromat. With oxygen In isopropyl alcohol at 75℃; for 1h;

Reference： [1]Inoki, Satoshi; Kato, Koji; Takai, Toshihiro; Isayama, Shigeru; Yamada, Tohru; Mukaiyama, Teruaki [Chemistry Letters, 1989, p. 515 - 518]
[2]Inoki, Satoshi; Kato, Koji; Takai, Toshihiro; Isayama, Shigeru; Yamada, Tohru; Mukaiyama, Teruaki [Chemistry Letters, 1989, p. 515 - 518]
[3]Inoki, Satoshi; Kato, Koji; Takai, Toshihiro; Isayama, Shigeru; Yamada, Tohru; Mukaiyama, Teruaki [Chemistry Letters, 1989, p. 515 - 518]
[4]Mukaiyama, Teruaki; Isayama, Shigeru; Inoki, Satoshi; Kato, Koji; Yamada, Tohru; Takai, Toshihiro [Chemistry Letters, 1989, p. 449 - 452]
[5]Kato; Yamada; Takai; Inoki; Isayama [Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 1, p. 179 - 186]
  • 7
  • [ 872-05-9 ]
  • [ 124-18-5 ]
  • [ 693-54-9 ]
  • [ 334-48-5 ]
  • [ 1654-86-0 ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 7% 3: 3% 4: 5% With sodium tetrahydroborate; sulfuric acid; dichromic acid; acetic acid; <i>tert</i>-butyl alcohol multistep reaction, other substrates;
Reference： [1]Periasamy, M.; Narayana, C.; Anitha, N. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 844 - 846]
  • 8
  • [ 872-05-9 ]
  • [ 1120-06-5 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
1: 25% 2: 59% With oxygen; isopropyl alcohol at 75℃; for 8h;
1: 10 % Chromat. 2: 73 % Chromat. With triethylsilane; oxygen In propan-1-ol at 75℃; for 4h;
With phenylsilane; oxygen; sodium thiosulfate 1.) THF, r.t., 20 h; 2.) water, r.t., 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;
Reference： [1]Inoki, Satoshi; Kato, Koji; Takai, Toshihiro; Isayama, Shigeru; Yamada, Tohru; Mukaiyama, Teruaki [Chemistry Letters, 1989, p. 515 - 518]
[2]Isayama, Shigeru; Mukaiyama, Teruaki [Chemistry Letters, 1989, p. 569 - 572]
[3]Isayama, Shigeru; Mukaiyama, Teruaki [Chemistry Letters, 1989, p. 1071 - 1074]
  • 9
  • [ 693-54-9 ]
  • [ 105-21-5 ]
  • [ 104-50-7 ]
  • [ 1117-74-4 ]
  • [ 3128-06-1 ]
Reference： [1]Journal of applied chemistry of the USSR,1981,vol. 54,p. 726 - 730
    Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1981,vol. 54,p. 885 - 890
  • 10
  • [ 693-54-9 ]
  • [ 105-21-5 ]
  • [ 104-50-7 ]
  • [ 3128-06-1 ]
  • [ 123-76-2 ]
Reference： [1]Journal of applied chemistry of the USSR,1981,vol. 54,p. 726 - 730
    Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1981,vol. 54,p. 885 - 890
  • 11
  • [ 693-54-9 ]
  • [ 105-21-5 ]
  • [ 104-50-7 ]
  • [ 64-18-6 ]
  • [ 3128-07-2 ]
  • [ 112-05-0 ]
  • [ 64-19-7 ]
Reference： [1]Journal of applied chemistry of the USSR,1981,vol. 54,p. 726 - 730
    Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1981,vol. 54,p. 885 - 890
  • 12
  • [ 693-54-9 ]
  • [ 105-21-5 ]
  • [ 104-50-7 ]
  • [ 3128-07-2 ]
  • [ 123-76-2 ]
Reference： [1]Journal of applied chemistry of the USSR,1981,vol. 54,p. 726 - 730
    Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1981,vol. 54,p. 885 - 890
  • 13
  • [ 693-54-9 ]
  • [ 105-21-5 ]
  • [ 104-50-7 ]
  • [ 1117-74-4 ]
  • [ 123-76-2 ]
Reference： [1]Journal of applied chemistry of the USSR,1981,vol. 54,p. 726 - 730
    Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1981,vol. 54,p. 885 - 890
  • 14
  • [ 124-18-5 ]
  • [ 1565-81-7 ]
  • [ 1120-06-5 ]
  • [ 5205-34-5 ]
  • [ 112-30-1 ]
  • [ 693-54-9 ]
  • [ 2051-31-2 ]
YieldReaction ConditionsOperation in experiment
With oxygen for 1h; Heating; var. reaction times; also with PPh3 reduction of products; alternatively in the presence of 3-decanone, 3-decanol, 3-decyl hydroperoxide and 4-decyl hydroperoxide; autoxidation reaction;
Reference： [1]Goosen, Andre; Kindermans, Sybrandus [South African Journal of Chemistry, 1997, vol. 50, # 1, p. 9 - 13]
  • 15
  • [ 1120-06-5 ]
  • [ 33758-16-6 ]
  • (R)-decan-2-ol [ No CAS ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
97% With Tris-HCl buffer; Rhodococcus erythropolis DSM 312; acetone at 30℃; for 16h;
71% With Tris-HCl buffer; Rhodococcus erythropolis FCC 173; acetone at 30℃; for 16h;
47% With Tris-HCl buffer; Rhodococcus sp. NCIMB 11216; acetone at 30℃; for 16h;
With [bis(acetoxy)iodo]benzene; potassium bromide In diethyl ether; water at 20℃; for 0.5h; Title compound not separated from byproducts.;

Reference： [1]Voss, Constance V.; Gruber, Christian C.; Kroutil, Wolfgang [Tetrahedron Asymmetry, 2007, vol. 18, # 2, p. 276 - 281]
[2]Voss, Constance V.; Gruber, Christian C.; Kroutil, Wolfgang [Tetrahedron Asymmetry, 2007, vol. 18, # 2, p. 276 - 281]
[3]Voss, Constance V.; Gruber, Christian C.; Kroutil, Wolfgang [Tetrahedron Asymmetry, 2007, vol. 18, # 2, p. 276 - 281]
[4]Sahoo, Suman; Kumar, Pradeep; Lefebvre; Halligudi [Tetrahedron Letters, 2008, vol. 49, # 33, p. 4865 - 4868]
  • 16
  • [ 693-54-9 ]
  • [ 19009-56-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) NaBH4, (ii) MeSO2Cl, (iii) /BRN= 3587243/ 2: Zn, aq. AcOH / Cob(I)alamin / Ambient temperature
Reference： [1]Fischli [Helvetica Chimica Acta, 1978, vol. 61, # 7, p. 2560 - 2578]
  • 17
  • [ 693-54-9 ]
  • [ 598-99-2 ]
  • methyl 2-chloro-3-methylundec-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With chromium dichloride; In tetrahydrofuran; at 20℃; for 2.0h; In accordance with the general procedure described in Example 3 above, commercial ketone was converted to methyl 2-chloro-3-methyl-undec-2-enoate and as a colorless liquid in the indicated yield for Entry 1 in Table 2. [0050] Rf: 0.77 (15% EtOAc in hexane). 1H NMR (CDCI3, 300 MHz):( Major isomer)(AK-I-208-18): delta0.88 (t, 3H, J=6.9 Hz), 1.24-1.34 (m, 10H), 1.43-1.51 (m, 2H), 2.10 (s, 3H, -CH3), 2.50-2.55(m, 2H), 3.80 (s, 3H, CO2CH3). 13C NMR (CDCI3, 75 MHz): delta14.30, 22.66, 22.86, 28.38, 29.42, 29.58, 29.77, 32.06, 36.19, 52.65, 118.22, 151.75, 164.07. MS: m/z 246 (M+), 248 (M++2). 1H NMR (CDCI3, 300 MHz):( Minor isomer)(AK-I-208-20): delta0.88 (t, 3H, J=6.9 Hz), 1.24-1.26 (m, 10H), 1.43-1.53 (m, 2H), 2.15 (s, 3H, -CH3), 2.34-2.39 (m, 2H), 3.80 (s, 3H, CO2CH3). 13C NMR (CDCI3, 75 MHz): delta14.29, 21.22, 22.85, 26.81, 29.38, 29.57, 29.75, 32.05, 38.10, 52.66, 117.74, 151.80, 164.07. MS: m/z 246 (M+), 248 (M++2).
Reference： [1]Patent: US2004/143125,2004,A1 .Location in patent: Page 8
  • 18
  • [ 693-54-9 ]
  • [ 68760-65-6 ]
  • 7-methylpentadecene-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dimethyl sulfoxide In tetrahydrofuran; water; mineral oil II Synthesis of 7-methylpentadecene-1-ol Synthesis of 7-methylpentadecene-1-ol Into a dried 5L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g).
With dimethyl sulfoxide In tetrahydrofuran; water; mineral oil II Synthesis of 7-methylpentadecene-1-ol Synthesis of 7-methylpentadecene-1-ol Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g).
Reference： [1]Current Patent Assignee: PROCTER & GAMBLE CO - US6008181, 1999, A
[2]Current Patent Assignee: PROCTER & GAMBLE CO - US6093856, 2000, A
  • 19
  • copper(II) chloride dihydrate [ No CAS ]
  • [ 872-05-9 ]
  • [ 112-00-5 ]
  • palladium dichloride [ No CAS ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
2% In water; ethyl acetate; benzene; EXAMPLE 1 A mixture of copper (II) chloride dihydrate [10 mmol] and palladium (II) chloride [1.0 mmol] in water [10 ml] was stirred for 10 minutes at room temperature. Then 1-decene [3.51 g, 25 mmol] was added followed by benzene [15 ml] and dodecyltrimethylammonium chloride [2.0 mmol]. Oxygen was bubbled through the solution at 80 C. for 48 hours. After cooling to room temperature, ethyl acetate (15 ml) was added and the solution was filtered. The filtrate was dried using anhydrous magnesium sulphate, and then distilled to provide pure 2-decanone in 75% yield and 2-decene in 2% yield.
Reference： [1]Patent: US4568770,1986,A
  • 20
  • copper (11) chloride dihydrate [ No CAS ]
  • tris (triphenylphosphine) ruthenium (11) chloride [ No CAS ]
  • [ 872-05-9 ]
  • [ 112-00-5 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
64% In water; ethyl acetate; benzene; EXAMPLE 6 A mixture of copper (11) chloride dihydrate [10 mmol] and tris (triphenylphosphine) ruthenium (11) chloride [1.0 mmol] in water [10 ml] was stirred for 10 minutes at room temperature. Then 1-decene [3.51 g, 25 mmol] was added followed by benzene [15 ml] and dodecyltrimethylammonium chloride [2.0 mmol]. Oxygen was bubbled through the solution at 80 C. for 48 hours. After cooling to room temperature, ethyl acetate (15 ml) was added and the solution was filtered. The filtrate was dried using anhydrous magnesium sulphate, and then distilled to provide pure 2-decanone in 64% yield.
Reference： [1]Patent: US4568770,1986,A
  • 21
  • [ 693-54-9 ]
  • [ 1469-70-1 ]
  • [ 821787-14-8 ]
Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 3985 - 3994
[2]Angewandte Chemie - International Edition,2008,vol. 47,p. 7515 - 7519
[3]Chemistry - A European Journal,2011,vol. 17,p. 3985 - 3994
[4]European Journal of Organic Chemistry,2012,p. 1499 - 1503
  • 22
  • [ 124-18-5 ]
  • [ 1565-81-7 ]
  • [ 1120-06-5 ]
  • [ 5205-34-5 ]
  • [ 112-30-1 ]
  • [ 693-54-9 ]
  • [ 820-29-1 ]
  • [ 624-16-8 ]
  • [ 928-80-3 ]
  • [ 2051-31-2 ]
YieldReaction ConditionsOperation in experiment
With ferrous(II) sulfate heptahydrate; manganese sulfate pentahydrate; air; D-glucose; calcium chloride In water at 25℃; for 168h; Microbiological reaction; regioselective reaction;
With ferrous(II) sulfate heptahydrate; manganese sulfate pentahydrate; air; D-glucose; calcium chloride In water at 25℃; for 168h; Microbiological reaction; regioselective reaction;
Reference： [1]Location in patent: experimental part Oda, Shinobu; Isshiki, Kunio; Ohashi, Shinichi [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 1, p. 105 - 109]
[2]Location in patent: experimental part Oda, Shinobu; Isshiki, Kunio; Ohashi, Shinichi [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 1, p. 105 - 109]
  • 23
  • [ 124-18-5 ]
  • [ 1565-81-7 ]
  • [ 1120-06-5 ]
  • [ 5205-34-5 ]
  • [ 693-54-9 ]
  • [ 820-29-1 ]
  • [ 624-16-8 ]
  • [ 928-80-3 ]
  • [ 2051-31-2 ]
YieldReaction ConditionsOperation in experiment
With ferrous(II) sulfate heptahydrate; manganese sulfate pentahydrate; air; D-glucose; Beauveria Bassiana ATCC 7159; calcium chloride In water at 25℃; for 168h; Microbiological reaction; regioselective reaction;
Reference： [1]Location in patent: experimental part Oda, Shinobu; Isshiki, Kunio; Ohashi, Shinichi [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 1, p. 105 - 109]
  • 24
  • [ 124-18-5 ]
  • [ 1565-81-7 ]
  • [ 1120-06-5 ]
  • [ 5205-34-5 ]
  • [ 693-54-9 ]
  • [ 928-80-3 ]
  • [ 2051-31-2 ]
YieldReaction ConditionsOperation in experiment
With ferrous(II) sulfate heptahydrate; manganese sulfate pentahydrate; air; D-glucose; calcium chloride In water at 25℃; for 168h; Microbiological reaction; regioselective reaction;
Reference： [1]Location in patent: experimental part Oda, Shinobu; Isshiki, Kunio; Ohashi, Shinichi [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 1, p. 105 - 109]
  • 25
  • [ 124-18-5 ]
  • [ 1565-81-7 ]
  • [ 5205-34-5 ]
  • [ 693-54-9 ]
  • [ 624-16-8 ]
  • [ 928-80-3 ]
  • [ 2051-31-2 ]
YieldReaction ConditionsOperation in experiment
With ferrous(II) sulfate heptahydrate; manganese sulfate pentahydrate; air; D-glucose; calcium chloride In water at 25℃; for 168h; Microbiological reaction; regioselective reaction;
Reference： [1]Location in patent: experimental part Oda, Shinobu; Isshiki, Kunio; Ohashi, Shinichi [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 1, p. 105 - 109]
  • 26
  • [ 1120-06-5 ]
  • [ 693-54-9 ]
  • [ 112-05-0 ]
YieldReaction ConditionsOperation in experiment
24% With dihydrogen peroxide In water; acetonitrile at 80℃; for 4h;
Reference： [1]Location in patent: experimental part Stolle, Achim; Ondruschka, Bernd; Morgenthal, Ingrid; Andersen, Olaf; Bonrath, Werner [Journal of Molecular Catalysis A: Chemical, 2011, vol. 335, # 1-2, p. 228 - 235]
  • 27
  • [ 693-54-9 ]
  • [ 16308-68-2 ]
  • [ 821787-14-8 ]
Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 3985 - 3994
  • 28
  • [ 5554-54-1 ]
  • [ 693-54-9 ]
  • [ 1294503-93-7 ]
YieldReaction ConditionsOperation in experiment
5% With N-benzyl-trimethylammonium hydroxide; ammonium chloride In dimethyl sulfoxide at 20 - 50℃; for 4.5h;
Reference： [1]Location in patent: experimental part Yamasaki, Toshihide; Ito, Yuko; Mito, Fumiya; Kitagawa, Kana; Matsuoka, Yuta; Yamato, Mayumi; Yamada, Ken-Ichi [Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 4144 - 4148]
  • 29
  • [ 124-18-5 ]
  • [ 1565-81-7 ]
  • [ 1120-06-5 ]
  • [ 112-30-1 ]
  • [ 111-14-8 ]
  • [ 124-07-2 ]
  • [ 693-54-9 ]
  • [ 928-80-3 ]
  • [ 112-05-0 ]
  • [ 334-48-5 ]
  • [ 2051-31-2 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); oxygen; triphenylphosphine at 90℃; for 2h; Autoclave;
Reference： [1]Location in patent: scheme or table Lloyd, Rhys; Jenkins, Robert L.; Piccinini, Marco; He, Qian; Kiely, Christopher J.; Carley, Albert F.; Golunski, Stanislaw E.; Bethell, Donald; Bartley, Jonathan K.; Hutchings, Graham J. [Journal of Catalysis, 2011, vol. 283, # 2, p. 161 - 167]
  • 30
  • [ 124-18-5 ]
  • [ 1565-81-7 ]
  • [ 1120-06-5 ]
  • [ 111-14-8 ]
  • [ 693-54-9 ]
  • [ 928-80-3 ]
  • [ 112-05-0 ]
  • [ 2051-31-2 ]
  • [ 64-19-7 ]
  • [ 107-92-6 ]
  • [ 109-52-4 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); oxygen at 90℃; for 2h; Autoclave;
Reference： [1]Location in patent: scheme or table Lloyd, Rhys; Jenkins, Robert L.; Piccinini, Marco; He, Qian; Kiely, Christopher J.; Carley, Albert F.; Golunski, Stanislaw E.; Bethell, Donald; Bartley, Jonathan K.; Hutchings, Graham J. [Journal of Catalysis, 2011, vol. 283, # 2, p. 161 - 167]
  • 31
  • [ 693-54-9 ]
  • [ 16325-51-2 ]
  • 5-iodo-3-methyl-3-octyl-1,2-thiazinane 1,1-dioxide [ No CAS ]
  • 5-iodo-3-methyl-3-octyl-1,2-thiazinane 1,1-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trimethylsilyl iodide In neat (no solvent) at 20℃; for 23h; Overall yield = 63 %; Optical yield = 4 %de;
Reference： [1]Clarisse, Damien; Pelotier, Béatrice; Fache, Fabienne [Chemistry - A European Journal, 2013, vol. 19, # 3, p. 857 - 860]
  • 32
  • [ 693-54-9 ]
  • [ 112-14-1 ]
YieldReaction ConditionsOperation in experiment
83.7% With D-(+)-glucose In aq. buffer at 15℃; for 24h; 2.5 Biotransformations using whole cells and crude cell extract General procedure: Whole-cell biotransformations were performed using both growing and resting cells. For growing cells, 2 ml TB medium in a 15 ml Falcon tube was inoculated with a pre-culture of E. coli BL21-CodonPlus(DE3)-RP cells containing the recombinant plasmid with the BVMO gene. The cells were grown for 3 h at 30 °C and with shaking at 150 rpm. Immediately after adding IPTG, the biotransformation reaction was initiated by adding the substrate to a final concentration of 5 mM. To boost the regeneration of NADPH, glucose (25 mM) was also added at the moment of induction. Biotransformations were carried out for 16 h at 15 °C and at a shake rate of 150 rpm. The level of conversion was measured by comparing E. coli BL21-CodonPlus(DE3)-RP expressing BVMO3 with cells from the same E. coli strain carrying pET-22b(+) without the BVMO3 gene, that served also as a blank for side reactions.
With AFL838 recombinant BVMO from Aspergillus flavus NRRL3357 In methanol at 20℃; for 2h; Enzymatic reaction; regioselective reaction; 2.3 Biotransformations General procedure: Whole-cell biotransformations were performed in 40mL amber glass vials using 1mL reaction volumes. The biotransformation reaction mixture (BRM) consisted of 0.1g wet weight/mL in 200mM Tris-HCl (pH 8), 100mM glucose and 100mM glycerol. The reactions were initiated by the addition of substrate (10mM) dissolved in methanol. Reactions were performed at 20°C for 2h, where after the reactions were stopped and extracted using an equal volume (2 times 0.5mL) of ethyl acetate containing 2mM 1-undecanol or 2mM 3-octanol as internal standard. GC-MS analysis was carried out on a Finnigan Trace GC ultra (ThermoScientific) equipped with a FactorFour VF-5ms column (60m×0.32mm×0.25μm, Varian). Chiral separation (Table S2) was performed using either a Chiraldex G-TA or B-TA column (30m×0.25mm×0.12μm, Astec).
With Baeyer-Villiger monooxygenase from the genome of Acinetobacter radioresistens; NADPH In aq. phosphate buffer at 30℃; for 0.05h; Enzymatic reaction; 2.7. Steady state parameters General procedure: The steady state kinetic parameters for 4-phenyl-2-butanone, 2-octanone, 2-decanone and 2-dodecanonewere determined spectrophotometricallyby monitoring the NADPH consumption rates (AU/s) at340 nm with a series of concentrations of substrates. Samples in atotal volume of 0.5 mL contained 0.5 μM enzyme and 150 μM of cosubstrate.Reactions were carried out for 5 min at 30 °C in 50 mMpotassium phosphate buffer, pH 7.4.
With D-Glucose; Aspergillus flavus Baeyer-Villiger monooxygenase<SUB>AFL838</SUB>; nicotinamide adenine dinucleotide phosphate In aq. buffer at 20℃; for 8h; Enzymatic reaction; regioselective reaction; Biotransformations and Steady-state kinetics General procedure: Biotransformations were performed in amber glass vials (40 mL) in a total reaction volume of 1 mL. Whole-cell (WC) and cell-free extract (CFE) biotransformations were performed aspreviously described [7]. Reactions with purified BVMO were performed in 100 mM Tris-HCl buffer (pH 8) containing 2 μM BVMO, 0.5 U BmGDH, 100 mM glucose, 0.3 mMNADP+ and 10 mM substrate. Reactions were maintained at 20°C with shaking (200 rpm),where after they were extracted using an equal volume (2 x 0.5 mL) ethyl acetate containing either 2 mM 1-undecanol or 3-octanol as internal standard. GC-FID (and GC-MS forproduct identification) was performed on a Finnigan Trace GC ultra (ThermoScientific)equipped with a FactorFour VF-5ms column (60 m x 0.32 mm x 0.25 μm, Varian). Steadystatekinetics were performed by monitoring the oxidation of NADPH spectrophotometericallyat 340 nm (ε340 = 6.22 mM-1.cm-1) or 370 nm(ε370 = 2.70 mM-1.cm-1). To investigate optimal pH, temperature, stability and effect of organic solvents, reactions typically contained2 μM BVMO, 0.3 mM NADPH, 1 mM phenylacetone, 1% (v/v) methanol (100 mMTris-HCl, pH 8; 25°C).

Reference： [1]Bisagni, Serena; Smus̈, Justyna; Chávez, Georgina; Hatti-Kaul, Rajni; Mamo, Gashaw [Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 109, p. 161 - 169]
[2]Ferroni; Smit; Opperman [Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 107, p. 47 - 54]
[3]Catucci, Gianluca; Zgrablic, Ivan; Lanciani, Francesco; Valetti, Francesca; Minerdi, Daniela; Ballou, David P.; Gilardi, Gianfranco; Sadeghi, Sheila J. [Biochimica et Biophysica Acta - Proteins and Proteomics, 2016, vol. 1864, # 9, p. 1177 - 1187]
[4]Ferroni, Felix Martin; Tolmie, Carmien; Smit, Martha Sophia; Opperman, Diederik Johannes [PLoS ONE, 2016, vol. 11, # 7]
  • 33
  • [ 693-54-9 ]
  • [ 95-54-5 ]
  • C26H44N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With [Cp2Zr(H2O)2]+[OSO2C4F9]-2; In neat (no solvent); at 20℃; for 0.333333h; General procedure: A mixture of o-phenylenediamine (1 mmol) and ketones (2.5 mmol) was well stirred with 1a (0.02 mmol) at r.t. for 15-30 min. After completion of the reaction, CH2Cl2 (3×10 mL) was added to the reaction mixture and the catalyst was filtered for the next cycle of the reaction. The combined CH2Cl2 solution was removed by evaporation in vacuum and was then subjected to silica gel column chromatograph with ethyl acetate-n-hexane (2:8) as eluent to afford pure compound.
Reference： [1]Journal of Organometallic Chemistry,2015,vol. 785,p. 61 - 67
  • 34
  • [ 693-54-9 ]
  • [ 74-88-4 ]
  • [ 3396-02-9 ]
YieldReaction ConditionsOperation in experiment
93% With magnesium; In diethyl ether; at 25℃; for 48.0h;Inert atmosphere; GaldenHT135/200 = 1:1 (2 mL) was placed in a test tube(13 mm Phi × 105 mm), to which MeI (571 mg, 4.0 mmol) wasadded slowly using a glass pipette under argon. Anhydrous Et2O(1 mL) was added slowly, whereupon three layers formed. Mgpowder (98 mg, 4.0 mmol) was then added slowly, and floatedbetween the Galden and ether layers, whereupon four layersformed. Subsequently, a solution of 2-decanone (1a, 313 mg, 2.0mmol) in anhydrous Et2O (3 mL) was added to the ether layer.The bottom layer was stirred slowly at 25 C for 2 d, taking carenot to mix the four layers. The ether solution and Mg salt weretaken into a flask, to which hydrochloric acid (2 M) was addedto quench the reaction, while cooling in an ice bath. The organiclayer was separated, and the aqueous layer was extracted withEt2O. The organic layer was collected, dried over Na2SO4, andconcentrated. The residue was purified by column chromatographyon silica gel (hexane-Et2O, 3:1) to give 2-methyl-2-decanol (2a)13 (320 mg, 93%) as a colorless oil; 1H NMR (500MHz, CDCl3): delta = 1.47-1.43 (m, 2 H, C-CH2), 1.34-1.28 (m, 12 H,alkyl), 1.21 (s, 6 H, 2 × C-CH3), 0.88 (t, J = 7.1 Hz, 3 H, CH2-CH3);13C NMR (126 MHz, CDCl3): delta = 70.97, 43.95, 31.81, 30.12, 29.53,29.20, 29.13, 24.28, 22.58, 14.01.
Reference： [1]Synlett,2015,vol. 26,p. 1276 - 1280
  • 35
  • [ 1119-86-4 ]
  • [ 872-05-9 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
1: 51% 2: 5% With ammonium metavanadate In propan-1-ol at 225 - 235℃; for 16.6667h; Autoclave; Inert atmosphere; Sealed tube; 2 Example 2 - The influence of the gas phase In Example 2 - The influence of the gas phase In order to confirm that the composition of the gas phase had little effect on the 1-decene yield and the product distribution, a comparison of nitrogen, hydrogen, and carbon monoxide gas was made. Using the same reaction conditions as in Example 1, including the NH4V03 catalyst, the results are summarized in Table 2 below. It is evident that neither the hydrogen gas nor the carbon monoxide gas act as reductants during the reaction.
1: 49% 2: 10% With hexaammonium heptamolybdate tetrahydrate; Hexadecane; hydrogen In isopropyl alcohol at 250℃; for 584400h; Autoclave;
1: 11% 2: 23% With hexaammonium heptamolybdate tetrahydrate; Hexadecane In acetone at 250℃; for 13.3333h; Autoclave;
Reference： [1]Current Patent Assignee: TECHNICAL UNIVERSITY OF DENMARK - WO2016/101958, 2016, A1 Location in patent: Page/Page column 18
[2]Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele; Nielsen, Lasse B.; Fristrup, Peter [ACS Catalysis, 2015, vol. 5, # 6, p. 3638 - 3647]
[3]Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele; Nielsen, Lasse B.; Fristrup, Peter [ACS Catalysis, 2015, vol. 5, # 6, p. 3638 - 3647]
  • 36
  • [ 1119-86-4 ]
  • [ 112-30-1 ]
  • [ 872-05-9 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
1: 49% 2: 10% 3: 15% With hexaammonium heptamolybdate tetrahydrate; Hexadecane In isopropyl alcohol at 250℃; for 13.3333h; Autoclave;
1: 37% 2: 11% 3: 10% With hexaammonium heptamolybdate tetrahydrate; Hexadecane In ethanol at 250℃; for 13.3333h; Autoclave;
Reference： [1]Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele; Nielsen, Lasse B.; Fristrup, Peter [ACS Catalysis, 2015, vol. 5, # 6, p. 3638 - 3647]
[2]Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele; Nielsen, Lasse B.; Fristrup, Peter [ACS Catalysis, 2015, vol. 5, # 6, p. 3638 - 3647]
  • 37
  • [ 1119-86-4 ]
  • [ 1120-06-5 ]
  • [ 112-30-1 ]
  • [ 872-05-9 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
1: 36% 2: 13% 3: 11% 4: 7% With hexaammonium heptamolybdate tetrahydrate; Hexadecane In propan-1-ol at 250℃; for 13.3333h; Autoclave;
Reference： [1]Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele; Nielsen, Lasse B.; Fristrup, Peter [ACS Catalysis, 2015, vol. 5, # 6, p. 3638 - 3647]
  • 38
  • [ 1119-86-4 ]
  • [ 1120-06-5 ]
  • [ 872-05-9 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
1: 46% 2: 10% 3: 6% With hexaammonium heptamolybdate tetrahydrate; Hexadecane; nitrogen In isopropyl alcohol at 250℃; for 584400h; Autoclave;
1: 5% 2: 7% 3: 8% With ammonium metavanadate In acetone at 225 - 235℃; for 16.6667h; Autoclave; Inert atmosphere; Sealed tube; 1 Example 1 - Deoxydehyd ration of 1,2-decanediol Example 1 - Deoxydehyd ration of 1,2-decanediol In the following examples, unless something else is stated, 40 mmol of diol, 2.0 mmol of catalyst (5 mol%, calculated with respect to the amount of vanadium), 500 mg of hexadecane (internal standard), and 100 ml of solvent were mixed in a 300 ml PTFE cup and placed in a 400 ml autoclave with a magnetic stir bar and computer-controlled heating plate. The autoclave was sealed, pressurized with 10-25 bar of H2, N2, or CO and heated to 230 °C for 1000 min (corresponding to ~ 16 h at the reaction temperature); the temperature typically stabilized between 225 and 235 °C. When the system had cooled to room temperature, the pressure was released, the reaction mixture was filtered to remove a black precipitate and analyzed by GC (for determination of conversion and yields) and GC-MS (for observation and identification of other products). Comparison of solvents A number of primary or secondary monohydric Ci-Cio alcohol solvents were tested together with NH4V03 as the catalyst. In addition, their performance was compared to that of acetone and hexane as solvents. The yields of 1-decene (C=C), 2-decanone (C=0), 2-decanol (2°OH), and 1-decanol (l°OH) are provided below in Table 1. It is evident that using a primary or secondary monohydric Ci-Cio alcohol as the solvent results in a better selectivity of 1-decene than any of the comparative solvents.
Reference： [1]Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele; Nielsen, Lasse B.; Fristrup, Peter [ACS Catalysis, 2015, vol. 5, # 6, p. 3638 - 3647]
[2]Current Patent Assignee: TECHNICAL UNIVERSITY OF DENMARK - WO2016/101958, 2016, A1 Location in patent: Page/Page column 16; 17
  • 39
  • [ 872-05-9 ]
  • [ 2404-44-6 ]
  • [ 124-19-6 ]
  • [ 1120-06-5 ]
  • [ 693-54-9 ]
YieldReaction ConditionsOperation in experiment
With oxygen; isobutyraldehyde In methanol at 55℃; for 8h; Autoclave; Green chemistry; Catalytic aerobic oxidation with AgFeO2-graphene General procedure: The oxidation processes were performed in a glass inlay of a 32ml steel autoclave. The autoclave was conditioned by discharge and replenish with dioxygen. All autoclave loading was carried out under air and heated to the required temperature (55°C) in an oil bath. In a generic test, 2.0mmol of substrate was added to the reactor with 0.01g AgFeO2-G, 3.0mmol isobutyraldehyde as a co-oxidant. After purgation with O2, the reactor was pressurized to 1.5bar. The stirring rate was 350rpm. At the end of 8h the reactor was depressurized, the catalyst deleted via an external magnet (1.2T) and the product mixture was analyzed by gas chromatography and 1H NMR. The products were identified with authentic samples and 1H NMR. Conversions and yields were computed about the starting substrate. The reaction products were measured by gas chromatography and recognized by comparison with the retention time and spectral data to those of an authentic sample. To ensure reproducibility, each catalytic reaction was performed at least three times. For recycling experiments, after finishing the process, the nanocomposite was recollected using a magnet, washed with acetonitrile, dried and reused. GC circumstances with column Hp-5: carrier gas N2 flow=0.7mlmin-1, inlet temp 250°C, initial column temp 90°C, final column temp 190°C, sleep 10°C min-1.
Reference： [1]Hosseini, Seyed Majid; Hosseini-Monfared, Hassan; Abbasi, Vahideh; Khoshroo, Mohammad Reza [Inorganic Chemistry Communications, 2016, vol. 67, p. 72 - 79]
  • 40
  • [ 112-31-2 ]
  • [ 693-54-9 ]
  • 11-hydroxy-9-eicosanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: Decan-2-one With lithium diisopropyl amide In tetrahydrofuran; toluene at -70 - -40℃; for 1h; Inert atmosphere; Stage #2: caprinaldehyde In tetrahydrofuran; toluene at -40 - -30℃; for 1h; Inert atmosphere; 2 [Example 2] (LDA in base) As a reaction procedure, in a 500 mL four-necked flask under a nitrogen atmosphere, 52.5 m Mol of lithium hexamethyldisilazane (LHMDS) (1.3 M toluene solution, 40.4 mL) and 12 mL of tetrahydrofuran (THF) and cooled to -40 ° C. Substrate As a methyl ketone, 50 mmol of 2-decanone (9.47 mL) and 10 mL of T HF was added dropwise within the range where the internal temperature did not exceed -70 ° C. and stirred for 1 hour. Next, the group 50 mmol of decanal (9.41 mL) as an aldehyde and 10 mL of TH F was added dropwise within the range not exceeding the internal temperature of -40 ° C. and the temperature was raised to -30 ° C. over 1 hour (Confirm the progress of the reaction). Next, as a reaction inactivation operation, 280 mmol of ammonium chloride (15 g) and water (50 mL) while keeping the temperature at 0 ° C. or less. Then As a neutralization operation, 50 mL of 2N hydrochloric acid was added at 20 ° C. or lower and neutralized to pH = 6 to 8. Extraction As an operation, 50 mL of ethyl acetate was added to the system, stirred at 400 rpm-5 min, and separated The operation was repeated three times, the obtained organic phase was washed with ultrapure water and saturated saline solution, and then the solvent To distill off 11-hydroxy-9-eicosanone contained in the crude product obtained by distilling off the high-speed liquid The crude yield was quantified by lomografting (HPLC) and found to be 74% (11. 6 g). The obtained crude product was completely dissolved in hexane at 40 ° C. and recrystallized to obtain 7.1 g ( White solid of 45% isolated yield). From the 1 H-NMR measurement result shown below, the obtained white Identified that the color crystals are 11-hydroxy-9-eicosanone. The obtained white crystals It is confirmed by purity analysis by liquid chromatography that purity is 99% or more A base is used other than the lithium diisopropylamide (LDA) is changed, and in the same method as the embodiment 1 was synthesized keto, 75% the yield of roughness
Reference： [1]Current Patent Assignee: KURARAY CO LTD - JP2016/124788, 2016, A Location in patent: Paragraph 0033; 0040
  • 41
  • [ 112-80-1 ]
  • [ 7373-13-9 ]
  • [ 693-54-9 ]
  • [ 1731-92-6 ]
  • [ 6742-54-7 ]
YieldReaction ConditionsOperation in experiment
With mesoporous HZSM-5 zeolite; at 500℃; General procedure: Catalytic performance of catalysts was evaluated by catalytic cracking of ethanol and oleic acid in a fixed-bed quartz tube reactor(inner diameter: 20 mm; length: 380 mm). As a typical run, the catalyst(0.5 g) was loaded into reactor, and heated to a desired temperature inN2 stream (the flow rate: 40 mL/min). The feedstock (0.87 g) was then injected into the reactor by a syringe pump. After flowing out from the reactor, the reaction products were cooled. Liquid products were weighed and analyzed by GC-MS (QP5000, Shimadzu, Japan) equipped with a DB-WAX fused silica capillary column (30m×0.25mm×0.25 mum). The gaseous product was collected with a gas collecting bag,and analyzed by GC referring to the method as described in our previous study
Reference： [1]Applied Catalysis A: General,2019,vol. 575,p. 101 - 110
  • 42
  • [ 693-54-9 ]
  • [ 58-56-0 ]
  • [ 2487255-80-9 ]
YieldReaction ConditionsOperation in experiment
87% With toluene-4-sulfonic acid In toluene for 17h; Reflux; Dean-Stark; General method for the preparation pyridoxine acetals and ketals 2 General procedure: To 10.00 g (1 equiv) a suspension of pyridoxine hydrochloride 1 in 140 ml oftoluene were added para-toluenesulfonic acid monohydrate (2.1 equiv) and aldehyde(or ketone) (1.5 equiv). The reaction mixture was refluxed with a Dean-Stark trap for 17h. Then the solvent was evaporated under reduced pressure and the residue wasneutralized with aqueous solution of NaOH. The aqueous solution was washed with100 ml of chloroform, organic layer was separated and dried. The precipitate waswashed successively with petroleum ether, methyl tert-butyl ether, an aqueous alkalisolution and dried.
Reference： [1]Shtyrlin, Nikita V.; Pugachev, Mikhail V.; Sapozhnikov, Sergey V.; Garipov, Marsel R.; Vafina, Rusalia M.; Grishaev, Denis Y.; Pavelyev, Roman S.; Kazakova, Renata R.; Agafonova, Mariya N.; Iksanova, Alfiya G.; Lisovskaya, Svetlana A.; Zeldi, Marina I.; Krylova, Elena S.; Nikitina, Elena V.; Sabirova, Alina E.; Kayumov, Airat R.; Shtyrlin, Yurii G. [Molecules, 2020, vol. 25, # 18]

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