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Chemical Structure| 6938-66-5 Chemical Structure| 6938-66-5

Structure of 1-Bromodocosane
CAS No.: 6938-66-5

Chemical Structure| 6938-66-5

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Product Details of [ 6938-66-5 ]

CAS No. :6938-66-5
Formula : C22H45Br
M.W : 389.50
SMILES Code : CCCCCCCCCCCCCCCCCCCCCCBr
English Name :1-Bromodocosane
MDL No. :MFCD00013543
InChI Key :QYOXLKAKUAASNA-UHFFFAOYSA-N
Pubchem ID :81355

Safety of [ 6938-66-5 ]

Computational Chemistry of [ 6938-66-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 20
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 115.74
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

6.26
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

12.47
Log Po/w (WLOGP)?

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

9.2
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.

7.23
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

9.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

8.92

Water Solubility

Log S (ESOL):?

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

-8.79
Solubility 0.00000063 mg/ml ; 0.0000000016 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-12.49
Solubility 0.0000000001 mg/ml ; 0.0 mol/l
Class?

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

Insoluble
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

-9.55
Solubility 0.00000011 mg/ml ; 0.0000000003 mol/l
Class?

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

Poorly soluble

Pharmacokinetics

GI absorption?

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

Low
BBB permeant?

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

No
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

Yes
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

Yes
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.

0.18 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

1.0
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

1.0
Egan?

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

1.0
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

3.0
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

1.0 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<3.0
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)

4.89

Application In Synthesis of [ 6938-66-5 ]

* 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 [ 6938-66-5 ]

[ 6938-66-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 6938-66-5 ]
  • [ 124-40-3 ]
  • [ 21542-96-1 ]
YieldReaction ConditionsOperation in experiment
79% In ethanol at 70 - 75℃; for 24h;
In diethyl ether
Stage #1: 1-Bromodocosane; dimethyl amine In ethanol at 70 - 75℃; for 24h; Stage #2: With sodium hydroxide In hexane; water for 0.166667h; Further stages.;
  • 2
  • [ 6938-66-5 ]
  • [ 62-56-6 ]
  • [ 7773-83-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-Bromodocosane; thiourea In ethanol for 12h; Heating; Stage #2: With potassium hydroxide In ethanol for 4h; Heating;
  • 3
  • [ 6938-66-5 ]
  • [ 14130-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / NaN3; hexadecyltrimethylammonium bromide / H2O / 72 h / 80 - 90 °C 2: 70 percent / H2 / Pd/C / hexane / 3 h / 20 °C / 3206.4 Torr
Multi-step reaction with 2 steps 1: dimethylformamide / 12 h / 80 °C 2: NH2NH2*H2O / CHCl3 / 5 h / Heating
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C 2: methylamine / methanol / 16 h / 80 °C / Schlenk technique
  • 4
  • [ 6938-66-5 ]
  • [ 7773-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / aq. sodium thiosulfate pentahydrate / ethanol / 72 h / Heating 2: 87 percent / aq. HCl / 2 h / Heating
Multi-step reaction with 2 steps 1: tetrahydrofuran / 18 h / 80 °C 2: KOH / tetrahydrofuran / 0.5 h / 50 °C
  • 5
  • [ 6938-66-5 ]
  • [ 6949-73-1 ]
  • [ 1245574-80-4 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In N,N-dimethyl-formamide at 80℃; 1-1 Example 1 1-1: Synthesis of 2-docosyloxy-9-fluorenone 2-Hydroxy-9-fluorenone (196 mg, 2.04 mmol) was dissolved in DMF (8 ml), potassium carbonate (423 mg, 3.06 mmol) and docosyl bromide (96%, 785 mg, 1.93 mmol) were added. The mixture was heated to 80°C and stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, and 1N hydrochloric acid (4 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (23 ml), and washed once with 1N hydrochloric acid (7.5 ml) and 4 times with pure water (7.5 ml). The solvent of the organic layer was evaporated, and the residue was precipitated with methanol (10 ml) to give 2-docosyloxy-9-fluorenone (934 mg, 1.85 mmol, 96%). 1H-NMR (400MHz) 0.88 (3H, t, J=7.0, C21H42-Me) 1.20-1.40 (36H, br, alkyl-H) 1.45 (2H, br, -O-C2H4-CH2-C19H39) 1.79 (2H, m, -O-CH2-CH2-) 4.00 (2H, t, J=6.6, -O-CH2-) 6.97 (1H, fluorenone C3-H) 7.19 (2H, fluorenone C1,7-H) 7.38-7.43 (3H, fluorenone C4,5,6-H) 7.59 (1H, fluorenone C8-H) MS 505 [M+H]
With hydrogenchloride; potassium carbonate In water; N,N-dimethyl-formamide 1 1-1: Example 1 1-1: Synthesis of 2-docosyloxy-9-fluorenone 2-Hydroxy-9-fluorenone (196 mg, 2.04 mmol) was dissolved in DMF (8 ml), potassium carbonate (423 mg, 3.06 mmol), and docosyl bromide (96%, 785 mg, 1.93 mmol) were added. The mixture was heated to 80° C. and stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, and 1N hydrochloric acid (4 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (23 ml), and washed once with 1N hydrochloric acid (7.5 ml) and 4 times with pure water (7.5 ml). The solvent of the organic layer was evaporated, and the residue was precipitated with methanol (10 ml) to give 2-docosyloxy-9-fluorenone (934 mg, 1.85 mmol, 96%). 1H-NMR(400 MHz) 0.88 (3H, t, J=7.0, C21H42-) 1.20-1.40 (36H, br, alkyl-H) 1.45 (2H, br, -O-C2H4-C-C19H39) 1.79 (2H, m, -O-CH2-C-) 4.00 (2H, t, J=6.6, -O-C-) 6.97 (1H, fluorenone C3-H) 7.19 (2H, fluorenone C1,7-H) 7.38-7.43 (3H, fluorenone C4,5,6-H) 7.59 (1H, fluorenone C8-H)
  • 6
  • [ 1007882-58-7 ]
  • [ 6938-66-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: (S)-tert-butyl 2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate With hydrogen; sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: 1-Bromodocosane In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;
  • 7
  • [ 6938-66-5 ]
  • [ 605-32-3 ]
  • [ 1430074-47-7 ]
  • 8
  • [ 6938-66-5 ]
  • [ 403-01-0 ]
  • C30H51FO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% To <strong>[403-01-0]methyl 3-fluoro-4-hydroxybenzoate</strong> (850 mg) and potassium carbonate (3.5 g), 1,3-dimethyl-2-imidazolidinone(10 mL) was added, and the mixture was stirred at 70°C for 15 minutes. 1-Bromodocosane (2.1 g) was addedthereto, and the mixture was stirred at 70°C for 13 hours. Water (200 mL) was added to the reaction liquid, the solutionwas stirred, then the precipitate was collected by suction filtration and washed with acetonitrile (100 mL) to obtain thecompound represented by E39 (2.2 g, percent yield: 93percent). 1H NMR (500 MHz, CDCl3) delta 7.79 (1 H,br d J = 8.6 Hz), 7.73 (1 H, dd J = 11.7, 2.0 Hz), 6.96 (1 H, t J = 8.3Hz), 4.08 (2 H, t J = 6.6 Hz), 3.89 (3 H, s), 1.84 (2 H, m), 1.47 (2 H, m), 1.19-1.37 (36 H, br), 0.88 (3 H,t J = 7.0 Hz).
  • 9
  • [ 6938-66-5 ]
  • [ 40615-36-9 ]
  • [ 93-97-0 ]
  • [ 58-61-7 ]
  • [ 2923115-67-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 16 h / 60 °C 1.2: 3 h / 0 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine / ethyl acetate / 1 h / 0 - 20 °C
  • 10
  • [ 6938-66-5 ]
  • [ 2923115-67-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 16 h / 60 °C 1.2: 3 h / 0 - 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / ethyl acetate / 1 h / 0 - 20 °C
  • 11
  • [ 6938-66-5 ]
  • [ 361525-84-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
83% With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide
 

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