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[ CAS No. 6950-92-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 6950-92-1
Chemical Structure| 6950-92-1
Chemical Structure| 6950-92-1
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Product Details of [ 6950-92-1 ]

CAS No. :6950-92-1 MDL No. :MFCD00020609
Formula : C11H16O Boiling Point : -
Linear Structure Formula :- InChI Key :FQZPTDPHVFTOSY-UHFFFAOYSA-N
M.W : 164.24 Pubchem ID :81389
Synonyms :

Calculated chemistry of [ 6950-92-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.27
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 2.78
Log Po/w (SILICOS-IT) : 3.45
Consensus Log Po/w : 2.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.307 mg/ml ; 0.00187 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.356 mg/ml ; 0.00217 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.027 mg/ml ; 0.000164 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 6950-92-1 ]

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

Application In Synthesis of [ 6950-92-1 ]

* 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 [ 6950-92-1 ]

[ 6950-92-1 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 75-21-8 ]
  • [ 2633-66-1 ]
  • [ 6950-92-1 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; benzene
(i) Et2O, (ii) H2SO4; Multistep reaction;
  • 2
  • [ 4170-90-5 ]
  • [ 527-53-7 ]
  • [ 6950-92-1 ]
  • 5
  • [ 6950-92-1 ]
  • [ 25692-16-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine; thionyl chloride In diethyl ether
  • 6
  • [ 769-25-5 ]
  • (R)-1-mesitylethanol [ No CAS ]
  • [ 6950-92-1 ]
  • (S)-1-(2,4,6-trimethylphenyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,4,6-trimethylstyrene With benzo[1,3,2]dioxaborole In toluene at 20℃; for 2h; Stage #2: With sodium hydroxide; water; dihydrogen peroxide In toluene at 20℃; for 2h; Title compound not separated from byproducts;
  • 7
  • [ 6950-92-1 ]
  • [ 58047-52-2 ]
YieldReaction ConditionsOperation in experiment
99% With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine
78%
71% With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 4.33333h; Mesitylacetaldehyde;2-Mesitylethanol (0.99g, 6.0mmol) was dissolved in DCM (10.OmL, dry) and cooled to 0°C. l,l,l-Tris(acetyloxy)-lλ5,2-benziodoxol-3(lH)-one (Dess-Martin periodinane) in DCM (15 wt %, 2.8Og, 6.60mmol) was added dropwise over a period of 20 mins. The ice bath was removed and the reaction mixture was stirred at rt for 4h. NaOH (2N, 5mL) was added to the mixture and it was diluted with water (5mL). The layers were separated and the organic layer was washed with water, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel using heptane and EtOAc as eluant giving the title compound (0.69g, 71%). 1H NMR (CDCl3, 400MHz) δ 9.68-9.65 (m, IH), 6.94-6.90 (m, 2H), 3.75-3.71 (m, 2H), 2.29 (s, 3H), 2.27 (s, 6H).
  • 8
  • [ 75-21-8 ]
  • [ 576-83-0 ]
  • [ 6950-92-1 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 2,4,6-trimethylphenyl bromide With magnesium Stage #2: oxirane
Stage #1: 2,4,6-trimethylphenyl bromide With ethyl bromide; magnesium In tetrahydrofuran at 30℃; for 6.5h; Stage #2: oxirane In tetrahydrofuran at -15 - 20℃; for 12h;
  • 9
  • [ 6950-92-1 ]
  • [ 108-24-7 ]
  • [ 910470-67-6 ]
YieldReaction ConditionsOperation in experiment
82% With pyridine; dmap
  • 10
  • [ 6950-92-1 ]
  • [ 480-63-7 ]
  • [ 4408-60-0 ]
  • 11
  • [ 6950-92-1 ]
  • [ 910470-73-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6
  • 12
  • [ 6950-92-1 ]
  • [ 910470-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6 5: 72 percent / TfOH / Au(PPh3)CH3 / methanol; H2O
  • 13
  • [ 6950-92-1 ]
  • [3-(2-acetoxy-ethyl)-2,4,6-trimethyl-phenyl]-acetic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6 5: 72 percent / TfOH / Au(PPh3)CH3 / methanol; H2O 6: 67 percent / N-methylimidazole / Irradiation
  • 14
  • [ 6950-92-1 ]
  • acetic acid 2-(5,7-dimethyl-1-oxo-indan-4-yl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6 5: 72 percent / TfOH / Au(PPh3)CH3 / methanol; H2O 6: 17 percent / N-methylimidazole / 2-methyl-propan-2-ol / Irradiation
  • 15
  • [ 6950-92-1 ]
  • [ 910470-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2
  • 16
  • [ 6950-92-1 ]
  • [ 910470-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6 5: 72 percent / TfOH / Au(PPh3)CH3 / methanol; H2O
  • 17
  • [ 6950-92-1 ]
  • [ 60657-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6 5: 72 percent / TfOH / Au(PPh3)CH3 / methanol; H2O 6: 17 percent / N-methylimidazole / 2-methyl-propan-2-ol / Irradiation 7: 91 percent / K2CO3 / methanol 8: 43 percent / LDA
  • 18
  • [ 6950-92-1 ]
  • [ 65848-78-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6 5: 72 percent / TfOH / Au(PPh3)CH3 / methanol; H2O 6: 17 percent / N-methylimidazole / 2-methyl-propan-2-ol / Irradiation 7: 91 percent / K2CO3 / methanol
  • 19
  • [ 6950-92-1 ]
  • [ 65848-80-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 82 percent / pyridine; DMAP 2: 54 percent / I2; PhI(OOCCF3)2 3: 47 percent / Et3N / Pd(PPh3)2Cl2 4: 96 percent / KF; 18-crown-6 5: 72 percent / TfOH / Au(PPh3)CH3 / methanol; H2O 6: 17 percent / N-methylimidazole / 2-methyl-propan-2-ol / Irradiation
  • 20
  • [ 6950-92-1 ]
  • [ 302787-07-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 78 percent 2.1: n-BuLi / tetrahydrofuran; hexane 2.2: 58 percent / tetrahydrofuran; hexane / -90 - 20 °C
  • 21
  • [ 6950-92-1 ]
  • [ 302787-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 78 percent 2.1: n-BuLi / tetrahydrofuran; hexane 2.2: 58 percent / tetrahydrofuran; hexane / -90 - 20 °C 3.1: 95 percent / NaOH / H2O; methanol / 96 h / Heating 4.1: 90 percent / diethyl ether
  • 22
  • [ 6950-92-1 ]
  • [ 302787-08-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 78 percent 2.1: n-BuLi / tetrahydrofuran; hexane 2.2: 58 percent / tetrahydrofuran; hexane / -90 - 20 °C 3.1: 95 percent / NaOH / H2O; methanol / 96 h / Heating
  • 23
  • [ 480-63-7 ]
  • [ 6950-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: hydrogen; CO; benzene / 190 °C / Reagens 4: Octacarbonyldikobalt; Reagens 5: CoCO3
  • 24
  • [ 938-18-1 ]
  • [ 6950-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: hydrogen; CO; benzene / 190 °C / Reagens 4: Octacarbonyldikobalt; Reagens 5: CoCO3
  • 25
  • [ 6950-92-1 ]
  • [ 94762-03-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) TsCl, Py, (ii) /BRN= 4163558/ 2: aq. H2O2, AcOH / Heating
  • 26
  • [ 313273-69-7 ]
  • [ 6950-92-1 ]
  • 1-[2-(2,4,6-trimethyl-phenyl)-ethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-bromo-xanthine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran XII 1-[2-(2,4,6-trimethyl-phenyl)-ethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-bromo-xanthine EXAMPLE XII 1-[2-(2,4,6-trimethyl-phenyl)-ethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-bromo-xanthine Prepared by reacting 3-methyl-7-(3-methyl-2-buten-1-yl)-8-bromo-xanthine with 2-(2,4,6-trimethyl-phenyl)-ethanol in the presence of triphenylphosphine and diisopropylazodicarboxylate in tetrahydrofuran at ambient temperature Rf value: 0.40 (silica gel, methylene chloride/ethyl acetate=15:1) Mass spectrum (ESI+): m/z=459, 461 [M+H]+
  • 27
  • [ 6950-92-1 ]
  • 2-(dibutylamino)-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: sodium hydride / N,N-dimethyl-formamide 5: sodium hydride / N,N-dimethyl-formamide
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone 5: sodium hydride / N,N-dimethyl-formamide
  • 28
  • [ 6950-92-1 ]
  • 2-[bis(cyclopropylmethyl)amino]-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: sodium hydride / N,N-dimethyl-formamide 5: sodium hydride / N,N-dimethyl-formamide
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone 5: sodium hydride / N,N-dimethyl-formamide
  • 29
  • [ 6950-92-1 ]
  • 5-mesityl-3,7-dimethyl-2-piperidin-1-yl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: sodium hydride / N,N-dimethyl-formamide 5: sodium hydride / N,N-dimethyl-formamide
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone 5: sodium hydride / N,N-dimethyl-formamide
  • 30
  • [ 6950-92-1 ]
  • 4-chloro-5-mesityl-7-methyl-N,N-dipropyl-7H-pyrrolo[2,3-d]-pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: N,N-diethylaniline; trichlorophosphate 5: sodium hydride / N,N-dimethyl-formamide
  • 31
  • [ 6950-92-1 ]
  • [ 868373-48-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: N,N-diethylaniline; trichlorophosphate 5: sodium hydride / N,N-dimethyl-formamide 6: sodium hydroxide / water
  • 32
  • [ 6950-92-1 ]
  • [ 1304707-34-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone
  • 33
  • [ 6950-92-1 ]
  • C23H34N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone 5: sodium hydride / N,N-dimethyl-formamide
  • 34
  • [ 6950-92-1 ]
  • C16H17ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: N,N-diethylaniline; trichlorophosphate
  • 35
  • [ 6950-92-1 ]
  • [ 868372-54-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: sodium hydride / N,N-dimethyl-formamide
Multi-step reaction with 4 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone
  • 36
  • [ 6950-92-1 ]
  • 2-(diethylamino)-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: sodium hydride / N,N-dimethyl-formamide 5: sodium hydride / N,N-dimethyl-formamide
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone 5: sodium hydride / N,N-dimethyl-formamide
  • 37
  • [ 6950-92-1 ]
  • 2-(dipropylamino)-3,7-dimethyl-5-(2,4,6-trimethylphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: sodium hydride / N,N-dimethyl-formamide 5: sodium hydride / N,N-dimethyl-formamide
Multi-step reaction with 5 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine 2: trimethylsilyl bromide / dimethyl sulfoxide; acetonitrile 3: potassium carbonate / dimethyl sulfoxide 4: potassium carbonate / acetone 5: sodium hydride / N,N-dimethyl-formamide
  • 38
  • [ 6950-92-1 ]
  • [ 53-86-1 ]
  • [ 1333343-66-0 ]
YieldReaction ConditionsOperation in experiment
88% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;
  • 39
  • 1-ethyl-4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid [ No CAS ]
  • [ 6950-92-1 ]
  • 2,4,6-trimethylphenethyl 1-ethyl-4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
120 mg Stage #1: 1-ethyl-4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid; 2-(2,4,6-trimethylphenyl)ethanol With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water Inert atmosphere;
  • 41
  • [ 6950-92-1 ]
  • (E)-3-(4-methoxy-2-oxo-2H-pyran-6-yl)acrylic acid [ No CAS ]
  • (E)-2,4,6-trimethylphenethyl 3-(4-methoxy-2-oxo-2H-pyran-6-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
  • 42
  • [ 41841-19-4 ]
  • [ 6950-92-1 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4.5h; Inert atmosphere; 57.2.2 General procedure: 5.1.57.2. Step 2. To a suspension of LiAlH4 (14.56 g, 307 mmol) inTHF (150 mL) was added a solution of (3-fluorophenyl)acetate(25.80 g, 153 mmol) at 0 C for 30 min under N2 atmosphere. Thismixture was stirred at 0 C for 1 h and at rt 3 h, and then, the reactionwas quenched by the addition of saturated Rochel’s salt untilparticipating. This precipitate was collected off, and washed withTHF (500 mL). The filtrate was concentrated under reduced pressure.The residue was purified by column chromatography (SiO2,n-hexane/EtOAc = 5/1-3/1) to obtain 2-(3-fluorophenyl)ethanol(19.74 g, 92%) as colorless oil.
  • 43
  • [ 6950-92-1 ]
  • [ 98-59-9 ]
  • [ 94265-41-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine at 0 - 20℃; for 4h; 57.3.3 General procedure: 5.1.57.3. Step 3. To a solution of 2-(3-fluorophenyl)ethanol(25.26 g, 180 mmol) in pyridine (180 mL) was added TsCl(36.49 g, 186 mmol) at 0 C with silica gel blue tube. After stirringat rt for 4 h, the reaction was quenched by the addition of 2 N HCl (750 mL) at 0 C. This mixture was extracted with EtOAc (300 mL).The separable organic layer was washed with 2 N HCl (250 mL),H2O (200 mL), brine (100 mL), and dried over MgSO4, filtered, concentratedunder reduced pressure. The residue was purified by columnchromatography (SiO2, n-hexane/EtOAc = 10/1-5/1) to obtain2-(3-fluorophenyl)ethyl 4-methylbenzenesulfonate (38.54 g, 73%)as a colorless oil.
  • 44
  • [ 6950-92-1 ]
  • N-{1-[2-(2,4,6-trimethylphenyl)ethyl]-4-piperidinyl}-N-phenylpropionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus tribromide / tetrachloromethane / 1 h / 60 °C 2: triethylamine / toluene / 24 h / Reflux
  • 45
  • [ 6950-92-1 ]
  • C28H40N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus tribromide / tetrachloromethane / 1 h / 60 °C 2: triethylamine / toluene / 24 h / Reflux
  • 46
  • [ 6950-92-1 ]
  • N-{1-[2-(2,4,6-trimethylphenyl)ethyl]-4-piperidinyl}-N-benzylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus tribromide / tetrachloromethane / 1 h / 60 °C 2: triethylamine / toluene / 48 h / Reflux
  • 47
  • [ 6950-92-1 ]
  • [ 13139-14-5 ]
  • C27H34N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;
  • 48
  • [ 6950-92-1 ]
  • [ 3982-67-0 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 2-(2,4,6-trimethylphenyl)ethanol With potassium fluoride; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; N,N`-sulfuryldiimidazole In N,N-dimethyl-formamide; trifluoroacetic acid at 20℃; Inert atmosphere; Stage #2: With triethyl borane; tris-(trimethylsilyl)silane In tetrahydrofuran; N,N-dimethyl-formamide; trifluoroacetic acid at 20℃;
  • 49
  • [ 92-66-0 ]
  • [ 6950-92-1 ]
  • 4-(2,4,6-trimethylbenzyl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With cerium(III) chloride; 9,10-diphenylanthracene; C12H20N2NiO4(2+)*2Cl(1-); C16H23O2(1-)*K(1+); sodium phosphate In dimethyl sulfoxide; acetonitrile at 20℃; for 36h; Glovebox; Sealed tube; Irradiation;
  • 50
  • [ 6950-92-1 ]
  • 2-(2-fluoroethyl)-1,3,5-trimethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium fluoride; fluorosulfonyl fluoride; 18-crown-6 ether; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 23℃; for 1h; Inert atmosphere; General procedure C: General procedure: A 20 mL vial A and a 30 mL vial B were equipped with magnetic stir-bars, were capped with septum-fitted vial caps and connected by a polyethylene tube. Under nitrogen, Vial A was charged with SDI (5.53 mmol, 9.22 equiv) and anhydrous KF (14.7 mmol, 24.5equiv). To vial B was added THF (12 mL). A 3 mL syringe filled with excess of TFA (3.0 mL, 39.2 mmol) was added into the vial A at a rate of 9 mL/hr by a syringe pump. The tube in vial B was immersed into the solution after the first bubbles of SO2F2 appeared. Once bubbling of SO2F2 subsided, into vial B was inserted an empty balloon to increase the bubbling rate. When the bubbling had almost stopped, 6M NaOH (3.0mL) was slowly added into vial A. After completing generation of SO2F2, the tube was removed. Without opening the vial B, trifluorotoluene (1equiv) was added by a syringe into vial B as an internal standard. Without opening the vial B, an aliquot was taken by a syringe for quantitative 19F NMR analysis to confirm no TFA contaminant and quantify the amount of SO2F2 (Note: the chemical shift of the twoequivalent fluorines of SO2F2 appear at 33.8 ppm. Typically, about 1.5 to2.5 equivalents of SO2F2 were calculated to be in THF prior to additionof the other reagents). KF (4 equiv) and 18-crown-6 (4 equiv) were added into vial B. A reaction mixture of 3-Phenyl-1-propanol 1a (0.6mmol, 1 equiv), THF (4.0 mL), and DBU (1.8 mmol, 3 equiv) were added into vial B at 4 mL/hr by a syringe pump. An aliquot was taken for quantitative 19F NMR analysis after stirring for one hour (note: theamount of the aliquot is less than 0.1 mL which is less than 1% of the reaction solution). Caution: Reaction vials can become pressurized during the generation of SO2F2. Note: Picture of the assembly is availablein the SI
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