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[ CAS No. 81190-28-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 81190-28-5
Chemical Structure| 81190-28-5
Structure of 81190-28-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 81190-28-5 ]

CAS No. :81190-28-5 MDL No. :MFCD00236085
Formula : C7H5F9O Boiling Point : -
Linear Structure Formula :- InChI Key :WUKHWLIEBSRTRH-UHFFFAOYSA-N
M.W : 276.10 Pubchem ID :2775819
Synonyms :

Calculated chemistry of [ 81190-28-5 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 10.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.34
TPSA : 12.53 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 3.4
Log Po/w (WLOGP) : 7.03
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 4.28
Consensus Log Po/w : 3.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.119 mg/ml ; 0.000433 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.125 mg/ml ; 0.000454 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.05
Solubility : 0.245 mg/ml ; 0.000887 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.93

Safety of [ 81190-28-5 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241+P242+P243-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-P501 UN#:1993
Hazard Statements:H225-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 81190-28-5 ]

* 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 [ 81190-28-5 ]

[ 81190-28-5 ] Synthesis Path-Downstream   1~66

  • 1
  • [ 80233-96-1 ]
  • [ 81190-28-5 ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydroxide In water at 85℃; for 5h; Inert atmosphere; 2,2,3,3,4,4,5,5,5-Nonafluoropentyloxirane (2) Compound 1 (41.00 g, 0.10 mol) was placed in a 250 mL three-necked glass round-bottomed flask fitted with a thermometer jacket, dropping funnel, and a condenser and heated with stirring to 85°C. Aqueous NaOH (20 %, 30.00 g) was introduced using the dropping funnel. The reaction mixture was stirred for 5 h at 85°C. After cooling, the mixture was filtered and the organic phase was extracted with Et2O (3 x 50 mL) and the extracts were merged and washed with H2O (3 x 50 mL) and then dried by MgSO4. The epoxide was obtained after evaporating under reduced pressure (yields: 19.6 g, 71 %). νmax (KBr)/ cm-1 νCH 2938.6-3066.5, νC-F 1422.5, νC-O-C 1023.7-1134.7. δH (400 MHz, CDCl3) 2.24, 2.39 (2 x dm, 2H, CH2CF2), 2.60 (dd, 1H (a), CH2), 2.90 (t, 1H (b), CH2), 3.23 (dq, 1H, CH). δF (376 MHz, CDCl3) -81.7 (m, 3F, CF3), -114.3 (q, 2F, CF2), -125.1 (m, 2F, CF2), -126.6 (m, 2F, CF2).
71% With sodium hydroxide In water at 85℃; for 5h; Inert atmosphere; Synthesis of 3-perfluoro-n-butyl-1,2-epoxypropane (FBE) 41.00 g (0.10 mol) of compound FBIP was taken in a glassware and heated, while stirring, to 85 °C. Afterward, aqueous NaOH (20%, 30.00 g) was introduced into the dropping funnel. The reaction mixture was stirred for 5 h at 85 °C. After cooling, the mixture was filtered and the organic phase was extracted with Et2O and washed with H2O several times. After drying with MgSO4, the epoxide (a colorless oily liquid) was obtained after evaporating under reduce pressure with a yield of 71%. FT-IR (KBr): νCH 2938.6-3066.5 cm-1,νC-F 1422.5 cm-1, νC-O-C 1023.7-1134.7 cm-1. 1H NMR(400 MHz, CDCl3):δ 2.24, 2.39 (2 × dm, 2H, CH2CF2);2.60(dd, lH (a), CH2);2.90 (t, 1H (b), CH2);3.23 (dq, lH, CH).19F NMR (376 MHz, CDCl3):δ - 81.7 (m, 3F, CF3);- 114.3(q, 2F, CF2),- 125.1 (m, 2F, CF2),- 126.6 (m, 2F, CF2).
With potassium hydroxide In dichloromethane for 1h; Yield given;
  • 2
  • [ 81190-28-5 ]
  • [ 125672-24-4 ]
YieldReaction ConditionsOperation in experiment
70% With fluorhydrate de diisopropylamine at 110℃; for 3h;
  • 3
  • [ 110-91-8 ]
  • [ 81190-28-5 ]
  • 1-Morpholino-4,4,5,5,6,6,7,7,7-nonafluoro-2-heptanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% for 2h; Heating;
  • 4
  • [ 83310-91-2 ]
  • [ 81190-28-5 ]
YieldReaction ConditionsOperation in experiment
55% With potassium hydroxide In hexane for 16h; Heating;
  • 5
  • [ 868-77-9 ]
  • [ 81190-28-5 ]
  • 7,7,8,8,9,9,10,10,10-nonafluoro-5-hydroxy-3-oxadecyl methacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With di-tert-octylpyrocatechol; boron trifluoride diethyl etherate at 80℃; for 2h;
  • 6
  • [ 79-41-4 ]
  • [ 81190-28-5 ]
  • 4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptan-1-yl methacrylate [ No CAS ]
  • 4,4,5,5,6,6,7,7,7-nonafluoro-1-hydroxyheptan-2-yl methacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-tert-octylpyrocatechol; triethylamine at 100℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 7
  • [ 591-87-7 ]
  • [ 423-39-2 ]
  • [ 81190-28-5 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; Phthalic acid dibutyl ester 2.) hexane, reflux, 3 h; Yield given. Multistep reaction;
  • 8
  • [ 591-87-7 ]
  • [ 423-39-2 ]
  • [ 81190-28-5 ]
  • 3-(Nonafluoro-n-butyl)prop-2-enol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; Phthalic acid dibutyl ester 2.) Et2O, reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given;
  • 9
  • [ 81190-28-5 ]
  • 2-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)thiirane [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With thiourea In methanol for 4h; Heating;
  • 10
  • [ 81190-28-5 ]
  • 3-(Nonafluoro-n-butyl)prop-2-enol [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With potassium hydroxide In diethyl ether for 5h; Heating;
  • 11
  • [ 81190-28-5 ]
  • [ 67-64-1 ]
  • [ 196513-80-1 ]
YieldReaction ConditionsOperation in experiment
95% With boron trifluoride diethyl etherate for 0.5h; Heating;
  • 12
  • [ 83310-91-2 ]
  • [ 81190-28-5 ]
  • 3-(Nonafluoro-n-butyl)prop-2-enol [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With potassium hydroxide In hexane for 2.5h; Heating; Yields of byproduct given;
  • 13
  • [ 83310-91-2 ]
  • [ 81190-28-5 ]
  • 3-(Nonafluoro-n-butyl)prop-2-enol [ No CAS ]
  • Acetic acid (E)-4,4,5,5,6,6,7,7,7-nonafluoro-hept-2-enyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium hydroxide In diethyl ether for 5h; Heating; Yields of byproduct given;
With potassium hydroxide In diethyl ether for 5h; Heating; various solvents and time;
With potassium hydroxide In diethyl ether for 5h; Heating; Yield given. Title compound not separated from byproducts;
  • 14
  • [ 81190-28-5 ]
  • 4,4,5,5,6,6,7,7,7-Nonafluoro-2-hydroxy-heptanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With nitric acid; copper 1.) r.t., 12 h, 2.) 60-80 deg C, 48 h;
  • 15
  • [ 423-39-2 ]
  • [ 107-18-6 ]
  • [ 375-17-7 ]
  • [ 307-34-6 ]
  • [ 72016-05-8 ]
  • [ 81190-28-5 ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 25% 3: 8% 4: 7% With potassium hydroxide; 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 70℃; for 2h;
  • 16
  • [ 3663-46-5 ]
  • [ 81190-28-5 ]
  • 2,2,5-trimethyl-5-(6,6,7,7,8,8,9,9,9-nonafluoro-4-hydroxy-2-oxanonyl)-1,3-dioxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With boron trifluoride diethyl etherate at 90℃; for 2h;
  • 17
  • [ 81190-28-5 ]
  • [ 100-79-8 ]
  • 2,2-dimethyl-4-(6,6,7,7,8,8,9,9,9-nonafluoro-4-hydroxy-2-oxanonyl)-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With boron trifluoride diethyl etherate at 90℃; for 2h;
  • 18
  • [ 87-99-0 ]
  • [ 81190-28-5 ]
  • [ 67-64-1 ]
  • 2,3:4,5-di-O-isopropylidene-1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-DL-xylitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: XYLITOL; acetone With hydrogen cation Stage #2: 3‑(perfluoro‑n‑butyl)‑1,2‑epoxypropane With boron trifluoride diethyl etherate In di-isopropyl ether for 10h; Heating;
  • 19
  • [ 81190-28-5 ]
  • [ 4064-06-6 ]
  • 1,2:3,4-di-O-isopropylidene-6-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-α-D-galactopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With boron trifluoride diethyl etherate In di-isopropyl ether for 5h; Heating;
  • 20
  • [ 81190-28-5 ]
  • [ 60-24-2 ]
  • 2-(2-hydroxy-4,4,5,5,6,6,7,7,7-nonafluoroheptylsulfanyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In methanol for 24h; Heating;
  • 21
  • [ 123-90-0 ]
  • [ 81190-28-5 ]
  • N-(2-hydroxy-4,4,5,5,6,6,7,7,7-nonafluoroheptyl)thiomorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In isopropyl alcohol for 24h; Heating;
  • 23
  • [ 81190-28-5 ]
  • 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-DL-xylitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: H+ 1.2: BF3*Et2O / diisopropyl ether / 10 h / Heating 2.1: 75 percent / CF3COOH / H2O / 0.5 h / 20 °C
  • 24
  • [ 81190-28-5 ]
  • 6-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-D-galactopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / BF3*Et2O / diisopropyl ether / 5 h / Heating 2: 85 percent / CF3COOH / H2O / 0.5 h / 20 °C
  • 25
  • [ 81190-28-5 ]
  • 8,8,9,9,10,10,11,11,11-nonafluoro-4-oxaundecane-1,2,6-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / BF3*Et2O / 2 h / 90 °C 2: 89 percent / aq. HCl / methanol / 2 h / Heating
  • 26
  • [ 81190-28-5 ]
  • 8,8,9,9,10,10,11,11,11-nonafluoro-2-hydroxymethyl-2-methyl-4-oxaundecane-1,6-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / BF3*Et2O / 2 h / 90 °C 2: 88 percent / aq. HCl / methanol / 2 h / Heating
  • 27
  • [ 81190-28-5 ]
  • 4,4,5,5,6,6,7,7,7-Nonafluoro-2-hydroxy-heptanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / Cu, 60percent aq. HNO3 / 1.) r.t., 12 h, 2.) 60-80 deg C, 48 h 2: 91 percent / conc. H2SO4 / 5 h / Heating
  • 28
  • [ 81190-28-5 ]
  • [ 125070-38-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / BF3*Et2O / 0.5 h / Heating 2: 96 percent / aq. HCl, MeOH / 2 h / Heating
  • 29
  • [ 81190-28-5 ]
  • 4,4,5,5,6,6,7,7,7-nonafluoroheptane-1,2-diyl bis-methacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / BF3*Et2O / 0.5 h / Heating 2: 96 percent / aq. HCl, MeOH / 2 h / Heating 3: 81 percent / Et3N, di-tert-octylpyrocatechol / diethyl ether / 2 h / Ambient temperature
  • 30
  • [ 81190-28-5 ]
  • 1-Morpholinomethyl-3,3,4,4,5,5,6,6,6-nonafluorohexyl methacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / 2 h / Heating 2: 90 percent / CH2Cl2 / 5 h / Heating
YieldReaction ConditionsOperation in experiment
Preferable examples of epoxide D may include 3-trifluoromethyl-1,2-epoxypropane, 3-perfluoroethyl-1,2-epoxypropane, 3-perfluoropropyl-1,2-epoxypropane, 3-perfluorobutyl-1,2-epoxypropane, 3-perfluoropentyl-1,2-epoxypropane, 3-perfluorohexyl-1,2-epoxypropane, 3-perfluoroheptyl-1,2-epoxypropane, 3-perfluorooctyl-1,2-epoxypropane, 3-perfluorononyl-1,2-epoxypropane, ...
  • 32
  • [ 81190-28-5 ]
  • (+)-3-(nonafluorobutyl)-1,2-epoxypropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.9% With water In acetic acid; toluene at 0℃; for 7h;
  • 33
  • [ 81190-28-5 ]
  • poly[3-(nonafluorobutyl)-1,2-epoxypropane], atactic, Mn = 11000 g/mol, Mw/Mn = 1.9; monomer(s): (+)-3-(nonafluorobutyl)-1,2-epoxypropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With triisobutylaluminum In Hexafluorobenzene; toluene at 0℃; for 2h;
  • 34
  • [ 81190-28-5 ]
  • poly[3-(nonafluorobutyl)-1,2-epoxypropane], atactic, Mn = 14000 g/mol, Mw/Mn = 2.1; monomer(s): (+)-3-(nonafluorobutyl)-1,2-epoxypropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triisobutylaluminum In Hexafluorobenzene; toluene at 0℃; for 1h;
  • 35
  • [ 81190-28-5 ]
  • poly[3-(nonafluorobutyl)-1,2-epoxypropane], atactic, Mn = 17000 g/mol, Mw/Mn = 1.8; monomer(s): (+)-3-(nonafluorobutyl)-1,2-epoxypropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With triisobutylaluminum In Hexafluorobenzene; toluene at 0℃; for 2h;
  • 36
  • [ 201230-82-2 ]
  • [ 81190-28-5 ]
  • 4-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-2-propiolactone [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In 1,2-dimethoxyethane at 25℃; for 6h;
84% With [N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-phenylenediaminochromium-di-tetrahydrofuran]tetracarbonylcobaltate In 1,2-dimethoxyethane at 20 - 26℃; for 6h; Autoclave;
  • 37
  • [ 141-97-9 ]
  • [ 81190-28-5 ]
  • cis-3-acetyl-5-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)tetrahydrofuran-2-one [ No CAS ]
  • trans-3-acetyl-5-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)tetrahydrofuran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl acetoacetate; 3‑(perfluoro‑n‑butyl)‑1,2‑epoxypropane With sodium ethanolate In ethanol Stage #2: With acetic acid In ethanol
  • 38
  • [ 111-77-3 ]
  • [ 81190-28-5 ]
  • [ 1185746-40-0 ]
YieldReaction ConditionsOperation in experiment
93% With boron trifluoride diethyl etherate at 100℃; for 10h; Inert atmosphere; regioselective reaction;
  • 40
  • [ 488-43-7 ]
  • [ 81190-28-5 ]
  • [ 1232237-25-0 ]
YieldReaction ConditionsOperation in experiment
98% In 2,2,2-trifluoroethanol for 6h; Reflux;
YieldReaction ConditionsOperation in experiment
With 1-vinylimidazole at 20 - 250℃;
  • 43
  • [ 81190-28-5 ]
  • 1-trimethylammonium-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol, iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: acetonitrile / 24 h / 60 °C
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: 60 °C
  • 44
  • [ 81190-28-5 ]
  • 1-diethylmethylammonium-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol, iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: acetonitrile / 24 h / 60 °C
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: 60 °C
  • 46
  • [ 142-84-7 ]
  • [ 81190-28-5 ]
  • 1-dipropylamino-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol at 60℃;
  • 47
  • [ 142-84-7 ]
  • [ 81190-28-5 ]
  • 1-dipropylmethylammonium-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol, iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: 60 °C
  • 48
  • [ 111-92-2 ]
  • [ 81190-28-5 ]
  • 1-dibutylamino-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol at 60℃;
  • 49
  • [ 111-92-2 ]
  • [ 81190-28-5 ]
  • 1-dibutylmethylammonium-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol, iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: 60 °C
  • 50
  • [ 143-16-8 ]
  • [ 81190-28-5 ]
  • 1-dihexylamino-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol at 60℃;
  • 51
  • [ 143-16-8 ]
  • [ 81190-28-5 ]
  • 1-dihexylmethylammonium-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol, iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: 60 °C
  • 52
  • [ 1120-48-5 ]
  • [ 81190-28-5 ]
  • 1-dioctylmethylammonium-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol, iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 60 °C 2: 60 °C
  • 53
  • [ 1120-48-5 ]
  • [ 81190-28-5 ]
  • 1-dioctylamino-4,4,5,5,6,6,7,7,7-nonafluoroheptan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol at 60℃;
  • 54
  • [ 81190-28-5 ]
  • [ 118-97-8 ]
  • C14H8ClF9N2O7 [ No CAS ]
  • C14H8ClF9N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
10 parts of the compound represented by the formula (I-2-a), 0.041 part of the compound represented by the formula (I-2-c), 0.022 part of the compound represented by the formula (I-2-d) Part and methyl isobutyl ketone 50 parts were added, and the mixture was stirred at 23 C. for 30 minutes. To the resulting mixed solution, a compound represented by the formula (I-2-b) 13.44 parts of the compound to be added was added dropwise over 30 minutes and further stirred at 40 C. for 3 hours. The obtained reaction product was concentrated and the concentrated mass was separated by preparing a column (Kanto Chemical silica gel 60 N (spherical, neutral) 100-210 mum developing solvent: n-heptane / ethyl acetate = 1/1) 6.84 parts of the compound represented by the formula I-2-e) and 0.88 parts of the compound represented by the formula (I-5-e).
  • 55
  • [ 81190-28-5 ]
  • C14H8F9N2O10S(1-)*C18H15S(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetraethylammonium bromide; N-benzyl-N,N,N-triethylammonium chloride / 0.5 h / 23 °C 1.2: 3.5 h / 40 °C 2.1: sodium sulfite / acetonitrile / 3.5 h / 23 °C 3.1: methanol / 22.5 h / 23 °C
  • 56
  • [ 81190-28-5 ]
  • C14H8F9N2O10S(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetraethylammonium bromide; N-benzyl-N,N,N-triethylammonium chloride / 0.5 h / 23 °C 1.2: 3.5 h / 40 °C 2.1: sodium sulfite / acetonitrile / 3.5 h / 23 °C
  • 57
  • [ 81190-28-5 ]
  • C14H8F9N2O10S(1-)*C18H15S(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetraethylammonium bromide; N-benzyl-N,N,N-triethylammonium chloride / 0.5 h / 23 °C 1.2: 3.5 h / 40 °C 2.1: sodium sulfite / acetonitrile / 3.5 h / 23 °C 3.1: methanol / 22.5 h / 23 °C
  • 58
  • [ 81190-28-5 ]
  • C14H8F9N2O10S(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetraethylammonium bromide; N-benzyl-N,N,N-triethylammonium chloride / 0.5 h / 23 °C 1.2: 3.5 h / 40 °C 2.1: sodium sulfite / acetonitrile / 3.5 h / 23 °C
  • 59
  • [ 124-38-9 ]
  • [ 81190-28-5 ]
  • 4-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-1,3-dioxolan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With C102H123Al3N6O9; tetrabutylammomium bromide at 25℃; for 48h;
71% With tetrabutylammomium bromide In neat (no solvent) at 28℃; for 48h; Schlenk technique; Method A: General procedure: To a Schlenk tube, 1b (10.01 mg, 0.00433 mmol), TBAB (32.06 mg, 0.10 mmol), and stylene oxide 2a (115 mL, 1.00 mmol) were added. This reaction mixture was stirred under a CO2 atmosphere (ballon) at 28 °C for 48 h. The reaction mixture was diluted with AcOEt (6 mL) and transferred to a centrifugation tube. After centrifugation (2000 rpm, 20 min), the supernatant was removed and concentrated in vacuo. The obtained crude product was purified by silica gel column chromatography (hexane:AcOEt = 5:1) to afford 3a (108.3 mg, 66% yield)
  • 60
  • [ 81190-28-5 ]
  • C15H12F18O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / 0.5 h / 20 °C / Inert atmosphere 1.2: 10 h / 90 °C / Inert atmosphere 2.1: 1,3-bis(trifluoromethyl)benzene; tetrabutylammomium bromide; sodium hydroxide / water / 0.17 h / 20 °C / Inert atmosphere 2.2: 25 h / 45 °C / Inert atmosphere
  • 61
  • [ 81190-28-5 ]
  • C15H13Cl3F18O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: boron trifluoride diethyl etherate / 0.5 h / 20 °C / Inert atmosphere 1.2: 10 h / 90 °C / Inert atmosphere 2.1: 1,3-bis(trifluoromethyl)benzene; tetrabutylammomium bromide; sodium hydroxide / water / 0.17 h / 20 °C / Inert atmosphere 2.2: 25 h / 45 °C / Inert atmosphere 3.1: 1,3-bis(trifluoromethyl)benzene / 0.17 h / 70 °C / Inert atmosphere 3.2: 4 h / Inert atmosphere
  • 62
  • [ 355-28-2 ]
  • [ 81190-28-5 ]
  • C40H28F54O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 2,2,3,3,4,4,5,5,5-nonafluoropentanol With boron trifluoride diethyl etherate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3‑(perfluoro‑n‑butyl)‑1,2‑epoxypropane at 90℃; for 10h; Inert atmosphere; Poly[2,2,3,3,4,4,5,5,5-nonafluoropentyloxirane]glycol (3a-c) General procedure: Perfluorobutyl methanol (2.50 g, 0.01 mol) and BF3*Et2O (1.42 g, 0.01 mol) were charged into a 25 mL three-necked round-bottom flask and the mixture was stirred for 30 min at room temperature. Compound 2 (2.76 g, 0.01 mol) was then added slowly. The mixture was heated at 90°C for 10 h with stirring, and then distilled under vacuum to remove the unreacted perfluorobutyl methanol and gave pure product 3a (yield 4.71 g, 90 %).
  • 63
  • [ 355-28-2 ]
  • [ 81190-28-5 ]
  • C75H53F99O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 2,2,3,3,4,4,5,5,5-nonafluoropentanol With boron trifluoride diethyl etherate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3‑(perfluoro‑n‑butyl)‑1,2‑epoxypropane at 90℃; for 10h; Inert atmosphere; Poly[2,2,3,3,4,4,5,5,5-nonafluoropentyloxirane]glycol (3a-c) General procedure: Perfluorobutyl methanol (2.50 g, 0.01 mol) and BF3*Et2O (1.42 g, 0.01 mol) were charged into a 25 mL three-necked round-bottom flask and the mixture was stirred for 30 min at room temperature. Compound 2 (2.76 g, 0.01 mol) was then added slowly. The mixture was heated at 90°C for 10 h with stirring, and then distilled under vacuum to remove the unreacted perfluorobutyl methanol and gave pure product 3a (yield 4.71 g, 90 %).
  • 64
  • [ 355-28-2 ]
  • [ 81190-28-5 ]
  • C12H8F18O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 2,2,3,3,4,4,5,5,5-nonafluoropentanol With boron trifluoride diethyl etherate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3‑(perfluoro‑n‑butyl)‑1,2‑epoxypropane at 90℃; for 10h; Inert atmosphere; Poly[2,2,3,3,4,4,5,5,5-nonafluoropentyloxirane]glycol (3a-c) Perfluorobutyl methanol (2.50 g, 0.01 mol) and BF3*Et2O (1.42 g, 0.01 mol) were charged into a 25 mL three-necked round-bottom flask and the mixture was stirred for 30 min at room temperature. Compound 2 (2.76 g, 0.01 mol) was then added slowly. The mixture was heated at 90°C for 10 h with stirring, and then distilled under vacuum to remove the unreacted perfluorobutyl methanol and gave pure product 3a (yield 4.71 g, 90 %). νmax (KBr)/cm-1 νOH 3442.2, νCH 2882.2- 2983.8, νCF 1354.7, νC-O-C 1236.8. δH (400 MHz, CDCl3) 2.10- 2.33 (m, 2H, CH2CF2), 2.93 (s, 1H, OH), 4.05-4.23 (m, 1H, CHO), 3.33-3.82 (dd, 4H, 2 x CH2O). δF (376 MHz, CDCl3) -81.7 (m, 3F, CF3), -114.3 (q, 2F, CF2), -125.1 (m, 2F, CF2), -126.6 (m, 2F, CF2).
  • 65
  • [ 67-56-1 ]
  • [ 81190-28-5 ]
  • C8H9F9O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: methanol With boron trifluoride diethyl etherate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3‑(perfluoro‑n‑butyl)‑1,2‑epoxypropane at 90℃; for 10h; Inert atmosphere; Synthesis of poly (3-perfluoro-n-butyl-1,2-epoxypropane)oligomers (PFBE, n = 1, 5, 10) 1.60 g (0.05 mol) of methanol and 0.20 mL BF3·Et2O were added into a glassware and the mixture was stirred for 30 min at room temperature. The compound FBE (2.76 g, 0.01 mol) was added slowly. The mixture was heated to 90 °C and stirred for 10 h, then the unreacted methanol and BF3·Et2O were removed by rotary evaporation to obtain the pure product of PFBE (n = 1) (a colorless oily liquid) with a yield of 90%. FT-IR (KBr): νOH 3475.9 cm-1, νCH2931.2 cm-1, νC-O-C 1175.4 cm-1. 1H NMR (400 MHz,CDCl3):δ 2.10-2.33 (m, 2H, CH2CF2);2.93 (s, 1H, OH);4.05-4.23 (m, 1H, CHO), 3.33-3.82 (dd, 4H, 2 × CH2O).19FNMR (376 MHz, CDCl3):δ - 81.7 (m, 3F, CF3);- 114.3 (q,2F, CF2),- 125.1 (m, 2F, CF2),- 126.6 (m, 2F, CF2).
  • 66
  • [ 81190-28-5 ]
  • [ 83310-97-8 ]
YieldReaction ConditionsOperation in experiment
87% With ammonia borane; C28H28Cl2CoNP2; erbium(III) triflate In tetrahydrofuran at 45℃; for 8h;
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