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Chemical Structure| 78-69-3 Chemical Structure| 78-69-3

Structure of 3,7-Dimethyl-3-octanol
CAS No.: 78-69-3

Chemical Structure| 78-69-3

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Product Details of [ 78-69-3 ]

CAS No. :78-69-3
Formula : C10H22O
M.W : 158.28
SMILES Code : CCC(O)(C)CCCC(C)C
MDL No. :MFCD00004482
InChI Key :DLHQZZUEERVIGQ-UHFFFAOYSA-N
Pubchem ID :6548

Safety of [ 78-69-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 78-69-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 5
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 51.38
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.89
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

3.27
Log Po/w (WLOGP)?

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

2.97
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.

2.84
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

2.52
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.9

Water Solubility

Log S (ESOL):?

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

-2.55
Solubility 0.445 mg/ml ; 0.00281 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-3.37
Solubility 0.0676 mg/ml ; 0.000427 mol/l
Class?

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

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

-2.56
Solubility 0.439 mg/ml ; 0.00277 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.

-4.94 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)

2.1

Application In Synthesis of [ 78-69-3 ]

* 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 [ 78-69-3 ]

[ 78-69-3 ] Synthesis Path-Downstream   1~42

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  • [ 78-93-3 ]
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  • [ 144708-84-9 ]
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  • 20
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  • [ 676-99-3 ]
  • 1-ethyl-1,5-dimethylhexyl methylphosphonofluoridate [ No CAS ]
  • 23
  • 3,7-dimethyl-3-octyl pivalate [ No CAS ]
  • [ 78-69-3 ]
  • 24
  • [ 78-69-3 ]
  • [ 3282-30-2 ]
  • 3,7-dimethyl-3-octyl pivalate [ No CAS ]
  • 25
  • [ 78-69-3 ]
  • [ 999-97-3 ]
  • 3,7-dimethyl-3-trimethylsiloxyoctane [ No CAS ]
  • 26
  • [ 78-69-3 ]
  • 4-ethyl-4,8-dimethyl-1-nonene [ No CAS ]
  • 27
  • [ 78-69-3 ]
  • 1-(1-ethyl-1,5-dimethyl-hexyl)-naphthalene [ No CAS ]
  • 31
  • (<i>S</i>)-2-methyl-6-(toluene-4-sulfonyloxymethyl)-octane [ No CAS ]
  • [ 78-69-3 ]
  • 33
  • [ 1142814-79-6 ]
  • [ 78-69-3 ]
  • 36
  • [ 78-69-3 ]
  • [ 56523-31-0 ]
  • [ 6874-06-2 ]
  • [ 6874-31-3 ]
YieldReaction ConditionsOperation in experiment
With Amberlyst-15; In dichloromethane; for 2.5h;Reflux; General procedure: Amberlyst-15 (dry) (75 mg) was added to a dichloromethane solution (15 mL) of 4-(2-hydroxypropan-2-yl)-1-methylcyclohexanol (1a, trans-terpin) (75 mg; 0.43 mmol). The reaction was stirred at room temperature (rt) and monitored by TLC [diethyl ether/hexane (3:1) as eluent] until the verification of the disappearance of the reagent (3.5 h). The Amberlyst-15 was removed by filtration and the solvent was evaporated under reduced pressure at rt to give a residue. Dichloromethane (30 mL) was added to re-dissolve this residue. The organic phase was dried (Na2SO4), filtered and evaporated to dryness at rt to give 2-(4-methylcyclohex-3-enyl)propan-2-ol (2a) as a pale yellow oil (56.5 g; 85% yield). MS (EI), m/z 153 [M]+. 1H and 13C NMR spectra of 2a are identical to the described.10 This procedure was repeated for the five solvents tested (Table 2) and during dehydration yield optimization by variation of Amberlyst-15/alcohol 1a ratio (Fig. 1).
With pyridine; thionyl chloride; In dichloromethane; at -78℃; for 0.5h; This experiment was performed under modified condition in the literature;11 to a stirred solution of alcohol 1n (1.0 g; 6.30 mmol; 1.0 equiv) in dry dichloromethane (20 mL) at rt was added dry pyridine (1.02 mL; 12.60 mmol; 2.0 equiv). After cooling to -78 C a solution of thionyl chloride (2.2 mL; 31.50 mmol; 5.0 equiv) in dry dichloromethane (10 mL) and dry pyridine (4 mL; 50.40 mmol; 8.0 equiv) was added dropwise. The reaction mixture was stirred for 30 min at the same temperature before quenching with saturated aqueous NaHCO3 (30 mL). The reaction mixture was allowed to warm to rt and the organic layer was separated. The aqueous phase was extracted with dichloromethane (5×50 mL). The combined organic layers were dried over MgSO4 by filtration to give a crude (pale yellow) oil. This residue was further purified by conventional column chromatography (eluent: from hexane to hexane/EtOAc (3:6)) to give (0.70 g; 79% overall yield) of a mixture of olefins 2n' (82%), 2n (7%) and 2n (11%), ratio determined by NMR; see NMR data of mixture in Supplementary data.
With Filtrol 20X acidic clay; at 135℃; General procedure: To a 3 neck flask equipped with stirrer, thermocouple, and a glass spacer topped with a short path condenser was charged 168.53 g 2-butyl-1-octanol, and 4.03 g dried FILTROL 20× acidic clay catalyst. The mixture was heated to 160 C. with stirring and the pressure was reduced to 240 torr., and product was collected via distillation. Once distillation commenced the pressure was reduced to 160 torr over 20 minutes and the pot temperature fell to 135 C. After 2 h the system was cooled under vacuum. The two phase distillate was cooled causing the aqueous portion to freeze, i.e., placed in a commercial freezer overnight, and the organic portion was decanted. The aqueous phase was allowed to thaw and an additional 2 mL of organics were recovered and combined with the main organic portion to yield 88.28 g of a mixture of three C12 olefin isomers in roughly equal amounts, see table. Following the general procedure of Example 1, and adjusting the temperatures and pressures according to the volatility of the products, the alcohols of examples 2-6 were heated in the presence of FILTROL 20× acidic clay catalyst at the temperatures shown to produce a mixture of olefins V, Va and Vb.
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  • [ 18479-57-7 ]
  • 39
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  • [ 507-09-5 ]
  • C12H24OS [ No CAS ]
  • 40
  • [ 78-69-3 ]
  • 6-hydroperoxy-2,6-dimethyloctane [ No CAS ]
  • 41
  • [ 78-69-3 ]
  • 6-fluoro-3,7-dimethyloctan-3-ol [ No CAS ]
  • 42
  • [ 78-69-3 ]
  • [ 572-09-8 ]
  • C24H40O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.8 g With silver (II) carbonate; In dichloromethane; at 20℃; for 24h; Add 2g to the reaction flaskTetraacetyl substituted glucose bromine (chemical formula:), 0.38 g of <strong>[78-69-3]tetrahydrolinalol</strong> (chemical formula:),0.73g of silver carbonate and 10mL of dichloromethane,Reacting at room temperature for 24 hours;The solvent was removed under reduced pressure.Separated by column chromatography,The eluent (a mixture of petroleum ether and ethyl acetate in a mass ratio of 5:1) was washed down with 0.80 g of a white solid.That is, <strong>[78-69-3]tetrahydrolinalol</strong> tetraacetyl glucoside (chemical formula:).
 

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