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Chemical Structure| 1520-44-1 Chemical Structure| 1520-44-1

Structure of 1520-44-1

Chemical Structure| 1520-44-1

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Product Details of [ 1520-44-1 ]

CAS No. :1520-44-1
Formula : C16H18
M.W : 210.31
SMILES Code : CC(C1=CC=CC=C1)CCC2=CC=CC=C2
MDL No. :MFCD00506195
Boiling Point : No data available
InChI Key :PDINXYLAVFUHSA-UHFFFAOYSA-N
Pubchem ID :15203

Safety of [ 1520-44-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 1520-44-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 12
Fraction Csp3 0.25
Num. rotatable bonds 4
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 70.32
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.

2.82
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

5.01
Log Po/w (WLOGP)?

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

4.42
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.

5.83
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

4.81
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.58

Water Solubility

Log S (ESOL):?

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

-4.59
Solubility 0.00539 mg/ml ; 0.0000256 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-4.75
Solubility 0.00374 mg/ml ; 0.0000178 mol/l
Class?

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

Moderately 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

-6.17
Solubility 0.000144 mg/ml ; 0.000000684 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

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

Yes
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.

-4.03 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

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<2.0
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)

1.7

Application In Synthesis of [ 1520-44-1 ]

* 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 [ 1520-44-1 ]

[ 1520-44-1 ] Synthesis Path-Downstream   1~36

  • 3
  • [ 3277-89-2 ]
  • [ 98-86-2 ]
  • [ 1520-44-1 ]
  • 5
  • [ 4426-50-0 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 108-88-3 ]
  • [ 1520-44-1 ]
  • 7
  • [ 1520-44-1 ]
  • 1,3-Bis-<4-nitro-phenyl>-butan [ No CAS ]
  • 9
  • [ 1520-44-1 ]
  • [ 107-30-2 ]
  • 1,3-Bis-(4-chlormethyl-phenyl)-butan [ No CAS ]
  • 11
  • [ 616-21-7 ]
  • [ 71-43-2 ]
  • [ 719-79-9 ]
  • [ 1520-44-1 ]
  • [ 5223-61-0 ]
  • [ 13556-61-1 ]
  • 13
  • [ 292638-84-7 ]
  • [ 109-72-8 ]
  • [ 1083-56-3 ]
  • [ 54410-69-4 ]
  • [ 1520-44-1 ]
  • [ 52919-17-2 ]
  • 15
  • [ 292638-84-7 ]
  • [ 42808-98-0 ]
  • [ 1083-56-3 ]
  • [ 1520-44-1 ]
  • 19
  • [ 292638-84-7 ]
  • [ 1083-56-3 ]
  • [ 4013-34-7 ]
  • [ 1520-44-1 ]
  • [ 32345-80-5 ]
  • 20
  • [ 292638-84-7 ]
  • [ 100-41-4 ]
  • [ 7614-93-9 ]
  • [ 1520-44-1 ]
  • 22
  • [ 103-63-9 ]
  • [ 1083-56-3 ]
  • [ 1520-44-1 ]
  • [ 70547-85-2 ]
  • [ 42808-98-0 ]
  • 23
  • (S)-2-Phenyl-1-(2-phenyl-[1,3]dithian-2-yl)-propan-1-ol [ No CAS ]
  • [ 1520-44-1 ]
  • [ 5162-43-6 ]
  • [ 5162-42-5 ]
  • 25
  • [ 292638-84-7 ]
  • [ 100-41-4 ]
  • [ 1520-44-1 ]
  • [ 4613-11-0 ]
  • [ 2726-21-8 ]
  • 26
  • [ 7647-01-0 ]
  • [ 98-86-2 ]
  • after/according to/ Clemmensen amalgamated zinc [ No CAS ]
  • [ 292638-84-7 ]
  • [ 100-41-4 ]
  • [ 7614-93-9 ]
  • [ 1520-44-1 ]
  • 27
  • [ 7647-01-0 ]
  • [ 98-86-2 ]
  • in acidic solution amalgamated zinc [ No CAS ]
  • [ 292638-84-7 ]
  • [ 100-41-4 ]
  • [ 7614-93-9 ]
  • [ 1520-44-1 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 8 Bis-[(2,3-butanedione dioximato)(1-)N,N'](2-ethoxy-carbonylethyl)-(pyridine)cobalt(III), Agent 6, was prepared by the following method. A mixture of cobaltous chloride hexahydrate (11.9 g), and dimethylglyoxime (11.6 g) was dissolved, with stirring, in deaerated 90% ethanol (200 ml) under nitrogen. The following deaerated reagents were then added in sequence: sodium hydroxide (4 g in 25 ml water), pyridine (4 g), ethyl acrylate (5 g), sodium hydroxide (1 g in +-6 ml water). The resultant mixture was stirred for 5 minutes and then poured into water (500 ml) containing acetic acid (2.5 ml). The Agent was recovered by extraction of the aqueous mixture with methylene chloride, evaporation of the extract, and recrystallization of the residue from aqueous methanol. Treatment of MMA (1.9 g) with Agent 6 at 60 C. by the method of Example 4 yielded a mixture of oligomers consisting of dimer (0.8 g), trimer (0.6 g), plus higher oligomers.
EXAMPLE 16 Aquo(ethyl)(acacen)cobalt(III), Agent 16, was prepared by the following method. Cobaltous chloride hexahydrate (4.8 g) was dissolved in 20 ml of deaerated water under nitrogen. 4.5 g of (acacen), prepared by condensation of acetylacetone (2 mol) and ethylene diamine (1 mol), was then added, followed by sodium hydroxide (1.6 g). The mixture was heated, with stirring, until the suspended solid turned to a yellow-orange colour. The mixture was then cooled, the intermediate, (acacen)cobalt(II) filtered off under nitrogen and washed on the filter with warm deaerated water (10 ml), and then dried in-vacuo over calcium chloride. The air-sensitive anhydrous chelate (4.5 g) was dissolved in anhydrous tetrahydrofuran maintained under argon. Sodium amalgam (0.38 g sodium in 5 g mercury) was added, and the mixture stirred vigorously for 2 hours, then cooled to -10 C. Ethyl bromide (1.4 m) was added and the mixture stirred for 15 minutes, then decanted from the amalgam residues into water (100 ml). Agent 16 separated as brown crystals when the tetrahydrofuran was stripped under vacuum at 20 C.; it was purified by dissolution in acetone and crystallization on addition of water to the resultant green solution. Agent 16 crystallizes with water as the axial base; the water is eliminated when the Agent is dissolved in organic solvents. A labile orange-colored adduct is formed when a small quantity of pyridine is added to the green solution of Agent 16 or its chelate precursor. Agent 16 is stable in air, although loss of the ethyl group and oxidation of the residue occurs on prolonged storage at ambient temperatures. Treatment of MMA with Agent 16 using the method of Example 4 yielded poly(MMA) with molecular weight with 9,700 and polydispersity of 2.3. A similar treatment of addition of pyridine (8 mg) yielded polymer with molecular weight of 8,600, compared to the molecular weight of 18,000 obtained by treatment in the absence of the Agent or pyridine.
  • 31
  • α.γ-diphenyl-α-butylene [ No CAS ]
  • [ 1520-44-1 ]
  • 32
  • 1,3-diphenyl-butan-1-one semicarbazone [ No CAS ]
  • [ 1520-44-1 ]
  • 33
  • phenylmagnesium bromide [ No CAS ]
  • (+-)-4-methyl-1.3.2-dioxathiane-2.2-dioxide [ No CAS ]
  • [ 1520-44-1 ]
  • 34
  • <β-phenyl-propyl>-phenyl ketone [ No CAS ]
  • [ 1520-44-1 ]
  • 36
  • [ 292638-84-7 ]
  • [ 97-93-8 ]
  • [ 1083-56-3 ]
  • [ 104-51-8 ]
  • [ 135-98-8 ]
  • [ 1520-44-1 ]
 

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