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1,2-Octanediol
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[ CAS No. 1117-86-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 1117-86-8
Chemical Structure| 1117-86-8
Chemical Structure| 1117-86-8
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Quality Control of [ 1117-86-8 ]

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SDS Specification
Alternatived Products of [ 1117-86-8 ]

Product Details of [ 1117-86-8 ]

CAS No. :1117-86-8 MDL No. :MFCD00010738
Formula : C8H18O2 Boiling Point : -
Linear Structure Formula :- InChI Key :AEIJTFQOBWATKX-UHFFFAOYSA-N
M.W : 146.23 Pubchem ID :14231
Synonyms :

Calculated chemistry of [ 1117-86-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.89
TPSA : 40.46 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 1.31
Log Po/w (MLOGP) : 1.29
Log Po/w (SILICOS-IT) : 1.45
Consensus Log Po/w : 1.6

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.52
Solubility : 4.46 mg/ml ; 0.0305 mol/l
Class : Very soluble
Log S (Ali) : -2.32
Solubility : 0.699 mg/ml ; 0.00478 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.57
Solubility : 3.91 mg/ml ; 0.0267 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 1117-86-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P337+P313 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1117-86-8 ]

* 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 [ 1117-86-8 ]

[ 1117-86-8 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 111-66-0 ]
  • [ 1117-86-8 ]
YieldReaction ConditionsOperation in experiment
91.2% With formic acid; 3C38H80N(1+)*O16PW4(3-); dihydrogen peroxide; In water; at 40℃; for 2h;Green chemistry; General procedure: The catalytic reactions were performed in a 50 mL four-necked round-bottomed flask equipped with a reflux condenser. The assembly was kept in an isothermal water bath at a constant known temperature and mechanically agitated with an electric motor. The oxidation was carried out as follows: catalyst (0.12 mmol), terminal alkenes (30 mmol), H2O2 (30% aq., 40 mmol) and FA (60 mmol) were charged in the reaction flask. The catalyst/olefin ratio was 1:250 for all the reactions. When the oxidation reaction was over, the catalyst was precipitated from the reaction medium for further use when acetone was subsequently added to the solution, the precipitate was removed by centrifugation and filtration, and the filtrate extracted with CH2Cl2 (50 mL×3); the organic layer was collected and dried under anhydrous Na2SO4. After the evaporation of the solvent under reduced pressure, a solution of sodium hydroxide was added dropwise to the organic product to give high purity 1,2-diols. The organic product was analyzed by GC9600 using an internal standard method. Typical GC-MS analysis was also conducted to identify the products.
78.6% With formic acid; dihydrogen peroxide; oxalic acid; at 90 - 95℃; for 3.5h;Green chemistry; 1L reactor, stirrer, stirrer, dropper (separation funnel), condenser,With heating mantle, temperature sensor and thermostat100 g (0.86 mol) of 97% 1-octene and 20 g of oxalic acid dihydrate(18.6mol% relative to 1-octene at 0.16mol) and 99% formic acid60 g (1.29 mol) was added thereto, and the temperature was set to 95 C. while heating at 300 rpm, followed by heating.After reaching the set temperature, if the heating is stopped and the temperature is maintained at 95 ± 3 126 g of 35% hydrogen peroxide was added dropwise for 2 hours at a controlled rate.After the addition of hydrogen peroxide was completed, the reaction was further performed at 90 C. for 1.5 hours.The reaction was transferred to a separatory funnel, waited about 10 minutes, separated into an organic upper layer and a lower layer, and then separated an organic upper layer.The mass of the organic layer was measured at 145 g.Ejector connected to the tap water at 80 in the flask the organic upper layer(water pump) and then run for 1 hourPressure distillation gave 121 g of residue. GC the residue(Gas Chromatography) analysis92% 1,2-octanediol, 1% formyl ester of 1,2-octanediol,Contains 6% hexadecanolTo carry out the first liquid extraction separation, 50 ml of water and 50 ml of ethanol were added to the residue of 121 g, 100 ml of n-hexane was added, and the mixture was left to stand, resulting in an upper layer of about 80 ml.Remove the upper layer and rest the lower layer at 80It was distilled under reduced pressure for 1 hour in conjunction with a water pump connected with tap water to obtain about 107 g of a primary product.GC analysis of the first obtained product yielded 1,2-octanediol 98% (yield 83.4%),It was found to contain 1% hexadecanol.In order to carry out the second liquid extraction separation,50 ml of water and 50 ml of ethanol were further added to the first obtained product, and n-hexane was added.100 ml was added, then mixed well and left to yield about 70 ml of the top layer.The upper layer was removed, and the remaining lower layer was further distilled under reduced pressure for 2 hours by connecting a water pump connected to tap water at 80 C. to obtain about 99 g of a secondary product.GC analysis of the secondary obtained resulted in 1,2-octanediolIt was found to contain 99.8% (yield 78.6%).
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  • 2
  • [ 1117-86-8 ]
  • [ 108-24-7 ]
  • [ 22007-56-3 ]
YieldReaction ConditionsOperation in experiment
76% With dmap; triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice; mL of 1,2-octanediol, 10 mL of triethylamine, and 20 mg of dimethylaminopyridine were sequentially added to a 200 mL round bottom flask.100 mL of dichloromethane was slowly added dropwise with 6 mL of acetic anhydride under stirring in an ice bath.After the addition is complete, remove the ice bath.The system was stirred at room temperature for 16 hours.The reaction solution was washed with water, 1N hydrochloric acid,The mixture was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporatedFinally, the product was isolated by column chromatography (petroleum ether: ethyl acetate = 10:1).The isolated yield was 76%.
Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 3658 - 3667
[2]Patent: CN108707096,2018,A .Location in patent: Paragraph 0093; 0094; 0095
[3]Canadian Journal of Chemistry,1976,vol. 54,p. 2417 - 2425
[4]Tetrahedron,2004,vol. 60,p. 703 - 710
[5]Journal of Organic Chemistry,2012,vol. 77,p. 1610 - 1615
  • 3
  • [ 1117-86-8 ]
  • [ 7019-19-4 ]
YieldReaction ConditionsOperation in experiment
96% With potassium bromate; potassium hydrogensulfate; In water; at 20℃; for 24h;Darkness; General procedure: To a solution of 1,2-diol 1a (1.0 mmol) in water (4 mL), KBrO3 (0.5 mmol) was added followed by addition of KHSO4 (1.0 mmol). The reaction was conducted at room temperature under shielding from light until 1a disappeared, as monitored by TLC. After the reaction completion, aqueous saturated Na2S2O3 solution(10 mL) was added. The organic portion was extracted with AcOEt (3 40 mL)and then dried over MgSO4. The solvent was removed under vacuum and the residue was subjected to silica gel column chromatography (n-hexane/AcOEt5:1) to afford (134 mg, 94% yield) of product 2a.
85%Spectr. With (2,9-dimethyl-1,10-phenanthroline)-palladium(II) acetate; 2,6-dimethoxy-p-quinone; tetrabutylammonium tetrafluoroborate; acetic acid; In dimethyl sulfoxide; at 20℃; for 8h;Electrolysis; Inert atmosphere; General procedure: A homemade airtight electrolysis cell was used equipped with areticulated vitreous carbon (RVC) as working electrode (basi, USA),a bridged Ag/AgCl reference electrode with 2 M LiCl ethanol solution as inner solution and a 0.1 M Bu4NBF4 DMSO as bridge solution was used and the counter electrode, a platinum rod electrode, was put in a divided cell separated from the anodic partby a ceramic frit. In a typical electrolysis experiment 4 mL of a 0.2 MBu4NBF4 DMSO solution was added to the divided part followed bythe addition of 200 mL of acetic acid. In the anodic part neocuproinePd(OAc)2 (0.1 equivalent), 2,6-dimethoxybenzoquinone(0.6 equivalent) and the alcohol (0.7 mmol) was added to a 14 mL solution of 0.2 M Bu4NBF4 in DMSO. The cell was closed andput under an argon atmosphere. Stirring was started, next apotential of 0.7 V was applied. After the appropriate reaction time30 mL of water was added to the reaction mixture. The resultingmixture was extracted with tert-butylmethylether (3 times 25 mL).The collected organic layer was washed with 15 mL of water tofurther remove DMSO. Next the organic layer was dried withMgSO4 filtered and evaporated. The resulting solution wasexamined with NMR. Isolated products were obtained usingcolumn chromatography with heptane/ethylacetate (7/3) aseluent.
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  • 4
  • 8-<i>tert</i>-butyl-2-hexyl-1,4-dioxa-spiro[4.5]decane [ No CAS ]
  • [ 1117-86-8 ]
  • [ 98-53-3 ]
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[2]Tetrahedron,2003,vol. 59,p. 8989 - 8999
  • 5
  • [ 111-66-0 ]
  • [ 4312-99-6 ]
  • [ 1117-86-8 ]
  • [ 3391-86-4 ]
  • [ 2984-50-1 ]
YieldReaction ConditionsOperation in experiment
With 3-methylpentane; oxygen at 90℃; for 1 - 17h; 4 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a magnetic stirrer, were placed 3000 mg of 1-octene and 1000 mg of 3-methyl-pentane, followed by the addition of 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T] . The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.27 95.0 1.3 3.7 0 0 2 0.32 92.3 2.7 5.0 0 0 3.5 0.34 80.4 5.1 7.2 7.3 0 5 0.35 73.4 5.4 9.5 9.3 2.4 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With Isopropylbenzene; 2,2'-azobis(isobutyronitrile); oxygen at 90℃; for 1 - 17h; 13; 14 Example 13: Results obtained in the epoxidation of olefinic compounds in the presence of O2 with iso-propyl-benzene (cumene) as hydrocarbon and with the combination of catalysts of Examples 1 a and 2b [Au/CeO2 - CAT A] + [Ti-MCM-41-Sil. - CAT T], using azo-iso-butyronitrile (AIBN) as initiator or activator. Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a bar magnet, were placed 3000 mg of 1-octene, 1360 mg of iso-propyl-benzene (cumene) and 12 mg of AIBN (initiator), followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Example 1 a [Au/CeO2 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T]. The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.97 94.5 3.0 2.5 0 0 2 1.52 93.5 2.9 2.0 1.6 0 3.5 3.27 92.6 3.0 1.9 1.1 1.4 5 5.33 91.7 3.1 2.8 1.3 1.1 a- Epoxide= 1,2-epoxy-octane- b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.Example 14: Results obtained in the epoxidation of olefinic compounds with a constant and controlled feed of O2, with iso-propyl-benzene (cumene) as the hydrocarbon and with the combination of catalysts of Examples 1a and 2b [Au/CeO2 - CAT A] + [Ti-MCM-41-Sil. - CAT T], using azo-iso-butyronitrile (AIBN) as initiator or activator. Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a magnetic stirrer, were placed 3000 mg of 1-octene and 1360 mg of iso-propyl-benzene (cumene) and 12 mg of AIBN (initiator), followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Example 1 a [Au/CeO2 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T] . The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen, with a 10-bar pressure regulator, and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised at 10 bars with oxygen and this pressure is maintained constant throughout the process through the slow addition of oxygen into the system. The reaction temperature is raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products *100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonac Glycold Dimerse 3.5 3.33 92.4 3.1 2.1 1.2 1.2 7.0 6.52 91.5 3.1 2.8 1.4 1.2 10.5 8.74 89.9 3.5 3.5 1.6 1.8 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a bar magnet, were placed 3000 mg of 1-octene, 1360 mg of iso-propyl-benzene (cumene) and 12 mg of AIBN (initiator), followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Example 1 a [Au/CeO2 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T]. The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.97 94.5 3.0 2.5 0 0 2 1.52 93.5 2.9 2.0 1.6 0 3.5 3.27 92.6 3.0 1.9 1.1 1.4 5 5.33 91.7 3.1 2.8 1.3 1.1 a- Epoxide= 1,2-epoxy-octane- b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With 2,2'-azobis(isobutyronitrile); cyclohexane; oxygen at 90℃; for 1 - 17h; 11 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a bar magnet, were placed 3000 mg of 1-octene, 1360 mg of iso-propyl-benzene (cumene) and 12 mg of AIBN (initiator), followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Example 1 a [Au/CeO2 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T]. The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.97 94.5 3.0 2.5 0 0 2 1.52 93.5 2.9 2.0 1.6 0 3.5 3.27 92.6 3.0 1.9 1.1 1.4 5 5.33 91.7 3.1 2.8 1.3 1.1 a- Epoxide= 1,2-epoxy-octane- b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With 2,2'-azobis(isobutyronitrile); ethylbenzene; oxygen at 90℃; for 1 - 17h; 12 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a bar magnet, were placed 3000 mg of 1-octene, 1250 mg of ethyl-benzene and 12 mg of AIBN (initiator), followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Example 1a [Au/CeO2 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T]. The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant *100), and the selectivities of the products obtained (moles of product i / moles of total products *100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.64 88.3 3.1 4.6 4.0 0 2 1.98 86.7 2.6 4.7 3.8 2.2 3.5 3.44 85.0 3.6 4.0 5.3 2.1 5 4.89 86.1 3.6 4.2 4.3 1.8 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With 2,2'-azobis(isobutyronitrile); oxygen at 90℃; for 1 - 17h; 7 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a magnetic stirrer, were placed 3000 mg of 1-octene, 1000 mg of 1-methyl-pentane and 12 mg of AIBN (initiator), followed by the addition of 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T] . The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxide3 Enolb Enonec Glycold Dimerse 1 0.78 59.3 4.7 36.0 0 0 2 2.22 62.7 3.5 27.9 1.6 3.3 3.5 3.05 63.2 3.5 18.9 2.5 11.9 5 3.22 62.5 5.7 13.8 3.6 14.4 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With 2,2'-azobis(isobutyronitrile); 3-methylpentane; oxygen at 90℃; for 1 - 17h; 8 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a bar magnet, were placed 3000 mg of 1-octene, 1000 mg of 3-methyl-pentane and 12 mg of AIBN (initiator), followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Example 1 a [Au/CeO2 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil.CAT T]. The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products *100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.80 92.8 3.5 3.7 0 0 2 1.85 92.4 3.4 2.4 1.4 0.4 3.5 2.98 88.5 3.4 2.4 3.6 2.1 5 4.79 87.4 2.7 2.4 5.1 2.4 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With 2,2'-azobis(isobutyronitrile); 3-methylpentane; oxygen at 90℃; for 1 - 17h; 6 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a magnetic stirrer, were placed 3000 mg of 1-octene, 1000 mg of 3-methyl-pentane and 12 mg of AIBN, followed by the addition of 85 mg of a catalyst as described in Example 1 a [Au/CeO2 - CAT A]. The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 1.05 67.3 4.8 12.2 0 15.7 2 5.34 51.3 6.0 21.1 2.0 19.6 3.5 6.32 42.4 7.6 18.8 2.2 29.0 5 5.81 44.8 8.3 20.0 6.1 20.8 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With 2,2'-azobis(isobutyronitrile); 3-methylpentane; oxygen at 90℃; for 1 - 17h; 10 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a bar magnet, were placed 3000 mg of 1-octene, 1000 mg of 3-methyl-pentane and 12 mg of AIBN (initiator), followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Example 1 b [Au/MCM-41 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T] . The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 1.13 58.4 5.9 9.3 7.3 19.1 2 1.58 45.6 8.9 8.2 10.7 26.6 3.5 1.72 45.0 10.0 10.1 10.9 23.9 5 2.17 43.2 15.0 11.9 10.8 19.3 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.
With 2,2'-azobis(isobutyronitrile); 3-methylpentane; oxygen at 90℃; for 1 - 17h; 9 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a magnetic stirrer, were placed 3000 mg of 1-octene, 1000 mg of 3-methyl-pentane and 12 mg of AIBN (initiator), followed by the addition of 85 mg of a catalyst as described in Example 1 b [Au/MCM-41 - CAT A]. The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products *100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.21 11.5 11.5 8.5 12.4 18.7 2 0.63 11.2 18.9 7.4 10.1 26.6 3.5 1.24 10.0 27.4 21.3 5.1 39.2 5 1.49 15.6 26.7 25.6 4.8 40.3a- Epoxide= 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound.

Reference： [1]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 9
[2]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 13-14
[3]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 12
[4]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 12-13
[5]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 10
[6]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 10-11
[7]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 9-10
[8]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 11-12
[9]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - EP1876176, 2008, A1 Location in patent: Page/Page column 11
  • 6
  • [ 29684-56-8 ]
  • [ 1117-86-8 ]
  • [ 1189195-98-9 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; dichloromethane;Reflux; General procedure: The appropriate diol (0.5 mmol, 1.0 equiv) was dissolved in THF/CH2Cl2 (4:1, 5 mL) and the Burgess reagent (1.25 mmol, 2.5 equiv) was added at 25 C in a single portion. The resultant solution was immediately warmed to reflux (using a preheated oil bath) and stirred for 3-6 h. Upon completion, the reaction contents were cooled to 25 C, poured into saturated aqueous NH4Cl (25 mL), and extracted with CH2Cl2 (3×25 mL). The combined organic layers were then washed with water (50 mL), dried(Na2SO4), and concentrated. The resultant yellow residue was purified by flash column chromatography (silica gel) in an appropriate solvent system to give the desired product in high purity.
Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 7588 - 7591
[2]Tetrahedron,2011,vol. 67,p. 3111 - 3118
  • 7
  • [ 1219966-88-7 ]
  • [ 111-71-7 ]
  • [ 1117-86-8 ]
YieldReaction ConditionsOperation in experiment
1: 91% 2: 4% With water; oxygen; toluene-4-sulfonic acid at 100℃;
Reference： [1]Location in patent: scheme or table Wang, Azhong; Jiang, Huanfeng [Journal of Organic Chemistry, 2010, vol. 75, # 7, p. 2321 - 2326]
  • 8
  • [ 1219966-88-7 ]
  • [ 1117-86-8 ]
YieldReaction ConditionsOperation in experiment
88% With water; toluene-4-sulfonic acid at 100℃;
Reference： [1]Location in patent: scheme or table Wang, Azhong; Jiang, Huanfeng [Journal of Organic Chemistry, 2010, vol. 75, # 7, p. 2321 - 2326]
  • 9
  • [ 29684-56-8 ]
  • [ 1117-86-8 ]
  • [ 1189195-98-9 ]
Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2910 - 2921
  • 10
  • [ 1117-86-8 ]
  • [ 100-39-0 ]
  • [ 100011-00-5 ]
YieldReaction ConditionsOperation in experiment
47% To a stirred suspension of NaH (1.0 eq.) in DMF was added dropwise a solution of octanediol (1.0 eq.) in THF/DMF (2:1) at 0 C under argon. The mixture was stirred at 0 C for 2.0 h, and benzyl bromide (1.0 eq.) was added dropwise to the mixture at 0 C. After stirring at ambient temperature overnight, the cloudy white reaction mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, concentrated, and purified by flash column chromatography.
Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2950 - 2953
  • 11
  • [ 51792-34-8 ]
  • [ 1117-86-8 ]
  • 2-hexyl-2,3-dihydrothieno[3,4-b][1,4]dioxine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.5% With toluene-4-sulfonic acid; In toluene; for 30h;Reflux; 5 g (34.68 mmol) of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> (compound (1)), 5.6 g (38.15 mmol) of 1,2-octanediol, 99 mg (0.52 mmol) of p-toluenesulfonic acid monohydrate was added to 48 m of toluene and refluxed for 30 hours. After cooling to room temperature, the mixture was extracted 2 to 3 times with ether. It was then washed several times with 5% sodium hydroxide solution and distilled water, and water was removed with sodium sulfate (Na2SO4). After the solvent was removed, the silica gel column was purified to obtain 4.2 g of the compound (2) (yield: 53.5%).
Reference： [1]Journal of Nanoscience and Nanotechnology,2012,vol. 12,p. 4335 - 4339
[2]Journal of Nanoscience and Nanotechnology,2012,vol. 12,p. 3597 - 3601
[3]Patent: KR2019/68143,2019,A .Location in patent: Paragraph 0138-0142
[4]Macromolecules,2011,vol. 44,p. 9286 - 9294
  • 12
  • [ 111-66-0 ]
  • [ 4312-99-6 ]
  • [ 1117-86-8 ]
  • [ 3391-86-4 ]
YieldReaction ConditionsOperation in experiment
9 %Chromat. With lithium (S,S)-1,1'-(pyridine-2,6-diylbis(methylene))bis(pyrrolidine-2,1-diyl)diformate; dihydrogen peroxide; iron(II) acetate In methanol; water at 20℃; for 16.5h; Inert atmosphere; 3.12. Oxidative turnover reactions General procedure: Iron(II) acetate (12.0 mg, 0.070 mmol) was dissolved in degassed, dry methanol (1.20 mL) and an aliquot of this solution (0.200 mL) was added to a solution of ligand (4.00 mg, 0.010 mmol) in methanol (0.200 mL) under argon to give a yellow solution. The reaction was stirred for 1 h at room temperature under an atmosphere of argon, after which time it was diluted with methanol (10 mL) and the alkene substrate (10.00 mmol) was added. Hydrogen peroxide (30% solution in water, 13.0 μL, 0.100 mmol) in methanol (1.00 mL) was added over 30 min via syringe pump. The reaction was stirred at room temperature under argon for 16 h before the solution was concentrated in vacuo and diluted with ethyl acetate, then passed through a short silica column. The internal standard decane was added, and reaction mixtures were analysed by gas chromatography (GC). Products were identified unambiguously by comparison and spiking with authentic samples.
Reference： [1]Location in patent: experimental part Dungan, Victoria J.; Wong, Shwo Mun; Barry, Sarah M.; Rutledge, Peter J. [Tetrahedron, 2012, vol. 68, # 15, p. 3231 - 3236]
  • 13
  • [ 1117-86-8 ]
  • [ 141-75-3 ]
  • [ 65644-01-1 ]
YieldReaction ConditionsOperation in experiment
96% With pyridine; In Petroleum ether; at 20℃; General procedure: 2.2.1. General protocol A. The acylation of 1,2-alkanediols withacid chloride1,2-Alkanediol was dissolved in pyridine on slight heating;petroleum ether (PE) was added and the mixture was shaken untilhomogenization. Acid chloride was added dropwise on efcientmagnetic stirring. The mixture was stirred at RT for 0.25-16 hdepending on the target compound. Reaction was monitored byTLC. Methanol (0.5 ml) was added to the mixture when excessof acid chloride was used and stirring was continued for addi-tional 10 min. The reaction mixture was diluted with ethyl acetate(EtOAc) and aqueous NaHCO3 (10%) was added. Following the neutralization the water layer was separated, and the organic layerwashed twice with brine, dried over anhydrous MgSO4, ltered,concentrated and puried by ash chromatography over silica gel.(NB 1,2-Alkanediol bisbutyrates were used in preparative-scalelipase-catalyzed cleavage without previous purication.) The tar-get products were gained in 91-96% yields.;
Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2015,vol. 116,p. 60 - 69
[2]Journal of Organic Chemistry,2013,vol. 78,p. 12795 - 12801
  • 14
  • [ 1117-86-8 ]
  • [ 617-73-2 ]
Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 4305 - 4309
  • 15
  • [ 461-89-2 ]
  • [ 1117-86-8 ]
  • C19H35N3O4 [ No CAS ]
  • 2-(2-hydroxyoctyl)-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
7%Chromat.; 66% General procedure: To a double-necked round bottom flask (100mL), equipped with a condenser, it was added a mixture of KI (1.5mmol), P2O5 (1.5mmol) and the desired alcohol (1mmol) in DMF (5mL). The reaction mixture was stirred at r.t. for 30min. Next, the considered nucleobase (1mmol), K2CO3 (1mmol) and Et3N (1mmol) were added and the reaction mixture was heated to reflux for a further 6.5-10.5h (until TLC indicated no further progress in reaction, Table5). The solvent was then evaporated at reduced pressure, and the remaining foam was dissolved in chloroform (150mL) and washed with water (2×150mL). The organic layer was dried on Na2SO4 (1g) and evaporated. The product was purified using short column chromatography on silica gel eluting with proper solvents.
8%; 60% With potassium carbonate; 1-n-butyl-3-methylimidazolim bromide; triethylamine; p-toluenesulfonyl chloride; at 80℃; for 12h; General procedure: In a double-necked round-bottom flask (100 mL) wasadded a mixture consisting of nucleobase (0.01 mol),alcohol (0.012 mol), TsCl (2.86 g, 0.015), TEA (1.01 g,0.01 mol) and K2CO3 (1.38 g, 0.010 mol) in bmim[Br](10 mL). The flask was immersed in an oil bath, kept at80 C and stirred for the time when TLC indicated no furtherprogress in the conversion (Tables 4, 5, 6). The mixturewas then diluted with water (200 mL) and extracted withEtOAc (3 × 50 mL). The organic layer was dried (Na2SO4)and evaporated to afford the crude product which was purifiedby traditional column chromatography on silica geleluting with proper solvents.
Reference： [1]Tetrahedron,2019,vol. 75
[2]Journal of the Iranian Chemical Society,2015,vol. 12,p. 1603 - 1612
  • 16
  • [ 1117-86-8 ]
  • [ 105-53-3 ]
  • [ 706-14-9 ]
YieldReaction ConditionsOperation in experiment
52% With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); potassium carbonate In tert-Amyl alcohol at 150℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction;
Reference： [1]Peña-López, Miguel; Neumann, Helfried; Beller, Matthias [Chemical Communications, 2015, vol. 51, # 66, p. 13082 - 13085]
  • 17
  • [ 1117-86-8 ]
  • [ 124-38-9 ]
  • [ 115-19-5 ]
  • [ 115-22-0 ]
  • 4-hexyl-1,3-dioxolan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
69%Chromat.; 98% With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In acetonitrile; at 80℃; under 7500.75 Torr; for 24h;Autoclave; Sealed tube; General procedure: A 50-mL stainless steel autoclave equipped with a magnetic stir bar was charged with ZnCl2 (27.2 mg, 20 mol%), DBU (76 mg, 50 mol%), 4a (76.1 mg, 1 mmol), 2a (126.1 mg, 1.5 mmol), and CH3CN (2.0 mL) successively and sealed at r.t. The pressure was adjusted to 1 MPa with CO2 at the preset temperature (80 C) and the autoclave was heated at this temperature for 24 h. After the reaction was complete, the reactor was cooled in ice-water bath, and then excess CO2 was carefully vented. The mixture was diluted with EtOAc, and the yield of cyclic carbonate 5a and alpha-hydroxy ketone 6a was determined by gas chromatograph (Agilent 6890) equipped with a capillary column (HP-5 30 m * 0.25 mum) using a flame ionization detector using biphenyl (40 mg) as the internal standard. Then, the residue was obtained by removing the solvent under vacuum and further purified by column chromatography (petroleum ether/EtOAc 100:1-5:1) to obtain 5a and 6a.
Reference： [1]Synthesis,2019,vol. 51,p. 739 - 746
  • 18
  • [ 1117-86-8 ]
  • [ 124-38-9 ]
  • 4-hexyl-1,3-dioxolan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
> 99%Chromat. With 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-methyl-but-3-yn-2-ol; In N,N-dimethyl-formamide; at 120℃; under 22502.3 Torr; for 10h;Autoclave; General procedure: The reactions were performed in a 50 ml autoclave with a Teflon vessel inside equipped with magnetic stirring under 3.0 MPa CO2. After introducing DBU (60.8 mg, 0.4 mmol), propylene glycol (76.1 mg, 1 mmol), 2-methyl-3-butyn-2-ol (126.2 mg, 1.5 mmol), DMF (2 ml), the autoclave was sealed and filled with CO2 to keep thepressure of CO2 under 3.0 MPa. Then, the reaction mixture was stirred at 120 C for 10 h. When the reaction completed, the autoclave was cooled to ambient temperature and residual CO2 was carefully released. Subsequently, the mixture was flushed with DMF and analyzed by GC using biphenyl as an internal standard.
Reference： [1]Chinese Chemical Letters,2020,vol. 31,p. 341 - 344

Tags: 1117-86-8 synthesis path| 1117-86-8 SDS| 1117-86-8 COA| 1117-86-8 purity| 1117-86-8 application| 1117-86-8 NMR| 1117-86-8 COA| 1117-86-8 structure

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