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Chemical Structure| 694-82-6 Chemical Structure| 694-82-6

Structure of 694-82-6

Chemical Structure| 694-82-6

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Product Details of [ 694-82-6 ]

CAS No. :694-82-6
Formula : C6H9FO
M.W : 116.13
SMILES Code : FC1CCCCC1=O
MDL No. :MFCD01076476
InChI Key :VQYOFTVCYSPHPG-UHFFFAOYSA-N
Pubchem ID :11829404

Safety of [ 694-82-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H302-H314
Precautionary Statements:P210-P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378-P403+P233-P501
Class:8
UN#:3265
Packing Group:

Computational Chemistry of [ 694-82-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 0.83
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 29.09
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.28
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.23
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.89
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.18
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.54

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.33
Solubility 5.37 mg/ml ; 0.0462 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.19
Solubility 7.57 mg/ml ; 0.0652 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.43
Solubility 4.31 mg/ml ; 0.0372 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.14 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.13

Application In Synthesis of [ 694-82-6 ]

* 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 [ 694-82-6 ]

[ 694-82-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 1122-84-5 ]
  • [ 694-82-6 ]
  • 3
  • [ 694-82-6 ]
  • trans-2-Fluor-6-brom-cyclohexanon [ No CAS ]
  • 5
  • [ 29923-57-7 ]
  • [ 694-82-6 ]
  • 6
  • [ 108-94-1 ]
  • [ 694-82-6 ]
YieldReaction ConditionsOperation in experiment
With Selectfluor; In acetonitrile; at 80℃; for 24h;Inert atmosphere; To a solution of cyclohexanone (275 g, 2.80 mol) in ACN (2.75 L), under nitrogen, was added l-chloromethyl-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (1.09 kg, 3.08 mol). The resulting solution was stirred for 24 hours at 80C. The reaction was concentrated in vacuo, and the residue was dissolved in dichloromethane (2.00 L) and the insoluble materials were filtered off. The filtrate was washed with saturated aqueous NaHC03, dried over Na2S04, and concentrated in vacuo to afford an oil that was used as is in the next step.
  • 8
  • [ 76-09-5 ]
  • [ 694-82-6 ]
  • [ 129917-52-8 ]
  • 9
  • [ 6651-36-1 ]
  • [ 420-56-4 ]
  • [ 694-82-6 ]
  • 11
  • [ 50998-16-8 ]
  • [ 694-82-6 ]
  • 12
  • [ 71700-52-2 ]
  • [ 694-82-6 ]
  • 13
  • [ 694-82-6 ]
  • [ 64715-80-6 ]
  • [ 114156-17-1 ]
  • [ 114156-17-1 ]
  • 14
  • [ 694-82-6 ]
  • [ 108-94-1 ]
  • 2-fluoro-cyclohexylcyclohexanol [ No CAS ]
  • 16
  • [ 694-82-6 ]
  • 6-fluoro-5-hexenal [ No CAS ]
  • t-butyl 6-fluorohexanoate [ No CAS ]
  • 18
  • [ 694-82-6 ]
  • [ 108-91-8 ]
  • [ 114156-10-4 ]
  • 19
  • [ 694-82-6 ]
  • [ 107-21-1 ]
  • [ 89257-29-4 ]
  • 20
  • [ 694-82-6 ]
  • [ 107-11-9 ]
  • [ 128846-28-6 ]
  • 21
  • 3-(1-fluoro-2-oxocyclohexyl)propanenitrile [ No CAS ]
  • [ 694-82-6 ]
  • 4-Fluoro-9-oxo-non-8-enenitrile [ No CAS ]
  • (Z)-4-Fluoro-9-oxo-non-4-enenitrile [ No CAS ]
  • 1-Fluoro-6-hydroxy-bicyclo[4.2.0]octane-7-carbonitrile [ No CAS ]
  • 22
  • methyl 3-(1-fluoro-2-oxocyclohexyl)propanoate [ No CAS ]
  • [ 694-82-6 ]
  • 4-Fluoro-9-oxo-non-8-enoic acid methyl ester [ No CAS ]
  • (Z)-4-Fluoro-9-oxo-non-4-enoic acid methyl ester [ No CAS ]
  • 23
  • [ 694-82-6 ]
  • [ 115-11-7 ]
  • 5-fluoro-3,3-dimethyl-1-oxaspiro<3,5>nonane [ No CAS ]
  • 24
  • [ 1424-22-2 ]
  • [ 694-82-6 ]
YieldReaction ConditionsOperation in experiment
With fluorine; In acetonitrile; EXAMPLE 1 Through a stirred solution of 1-cyclohexenyl acetate (3.5 gm, 25 mmol) in dry acetonitrile (50 ml) was bubbled fluorine (50 mmol diluted to 10% v/v with nitrogen) over 110 mins. The reaction temperature was maintained at about 0 C. by cooling the reaction vessel externally. When the reaction was complete, the fluorine was switched off and the vessel was purged with nitrogen. The reaction mixture was then poured into water and thoroughly shaken before being extracted with dichloromethane. Most of the solvent was removed from the dried extracts under reduced pressure using a rotary evaporator. The residue was then distilled under reduced pressure using a short path distillation apparatus to give a main fraction (2.3 gm) which contained one major component (77% of total area of chromatogram) and several minor ones. A sample of the main component was isolated by preparative scale gas chromatography and identified as 2-fluorocyclohexanone (19 F NMR δ-188.7 ppm, d, JHF 48.7 Hz. 1 H NMR δ 4.96 ppm, dq, JHF 49 Hz, JHH 5.9 Hz, Multiplets at 2.6, 2.4, 2.1 and 1.7 ppm, M+ 116). Yield of 2-fluorocyclohexanone=61%.
  • 25
  • [ 1424-22-2 ]
  • [ 694-82-6 ]
  • [ 108-94-1 ]
  • 26
  • [ 4922-47-8 ]
  • [ 694-82-6 ]
  • (1,2-Difluoro-cyclohexylsulfanyl)-benzene [ No CAS ]
  • 27
  • [ 6651-36-1 ]
  • [ 502-44-3 ]
  • [ 694-82-6 ]
  • [ 108-94-1 ]
  • 30
  • sodium-compound of 2-hydroxymethylene-cyclohexanone [ No CAS ]
  • [ 694-82-6 ]
  • 31
  • [ 694-82-6 ]
  • [ 593-56-6 ]
  • 2-fluoro-cyclohexanone <i>O</i>-methyl-oxime [ No CAS ]
  • 32
  • [ 694-82-6 ]
  • 2-fluoro-cyclohexanone oxime [ No CAS ]
  • 2-fluoro-cyclohexanone oxime [ No CAS ]
  • 34
  • [ 694-82-6 ]
  • phenylmagnesium bromide [ No CAS ]
  • (1R,2R)-2-Fluoro-1-phenyl-cyclohexanol [ No CAS ]
  • 35
  • [ 14365-32-3 ]
  • [ 694-82-6 ]
YieldReaction ConditionsOperation in experiment
45% With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 - 0℃; General procedure: To a solution of oxalyl chloride (2.9 g, 23 mmol) in 40 ml of methylene chloride were added dropwise 3.6 ml (50 mmol) of DMSO in 10 ml of methylene chloride at -70 C. The trans-2-halogencycloalkanol (20 mmol) was added and the reaction mixture was stirred for 20 min. The temperature was then raised to -55 C and 16 ml of triethylamine was added. The reaction mixture was stirred for 20 min, warmed to 0 C, and poured into a 1 M hydrochloric acid solution. The water phase was separated and extracted with methylene chloride, the combined organic phases were washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was distilled under vacuum. rac-5a: yield 65%, bp 110 С (10 mmHg).22a 1H NMR (500 MHz, CDCl3): δ 1.40 (m, 1H, CH2), 1.60 (m, 2H, CH2), 1.90 (m, 1H, CH2), 2.10-2.31 (m, 2H, CH2), 2.45 (m, 2H, CH2), 5.21 (m, 1H, CHI). rac-5d: yield 45%, bp 70 С (10 mmHg).22b rac-6a: yield 65%, bp 100 С (10 mmHg).22c rac-5b, rac-5c, rac-6b;22c were prepared by known methods.
 

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