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Chemical Structure| 33537-99-4 Chemical Structure| 33537-99-4

Structure of 33537-99-4

Chemical Structure| 33537-99-4

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Product Details of [ 33537-99-4 ]

CAS No. :33537-99-4
Formula : C9H10ClN
M.W : 167.64
SMILES Code : ClC1=CC2=C(CNCC2)C=C1
MDL No. :MFCD06739156
InChI Key :NSURINBXOVVUNR-UHFFFAOYSA-N
Pubchem ID :11789594

Safety of [ 33537-99-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P330-P501

Computational Chemistry of [ 33537-99-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.33
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 50.79
TPSA ?

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

12.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.14
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

1.95
Log Po/w (WLOGP)?

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

1.45
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.

2.37
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

3.08
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.2

Water Solubility

Log S (ESOL):?

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

-2.51
Solubility 0.516 mg/ml ; 0.00308 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.

-1.83
Solubility 2.49 mg/ml ; 0.0149 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

-3.89
Solubility 0.0217 mg/ml ; 0.00013 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.

-5.94 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)

1.41

Application In Synthesis of [ 33537-99-4 ]

* 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 [ 33537-99-4 ]

[ 33537-99-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 62882-02-4 ]
  • [ 33537-99-4 ]
  • 2
  • [ 33537-99-4 ]
  • [ 13338-49-3 ]
  • [ 123593-86-2 ]
  • 3
  • [ 33537-99-4 ]
  • [ 81237-66-3 ]
  • 4
  • [ 33537-99-4 ]
  • [ 88-89-1 ]
  • [ 33537-98-3 ]
  • 6
  • N,N-bis(p-chlorobenzylamino)ethane dihydrobromide [ No CAS ]
  • [ 33537-99-4 ]
  • [ 104-86-9 ]
  • 8
  • 2-acetyl-6-chloro-1,2,2,4-tetrahydroisoquinoline [ No CAS ]
  • [ 33537-99-4 ]
  • 9
  • [ 1120-87-2 ]
  • [ 33537-99-4 ]
  • 6-Chloro-2-pyridin-4-yl-1,2,3,4-tetrahydro-isoquinoline [ No CAS ]
  • 10
  • [ 33537-99-4 ]
  • 8-{4-[2-(6-chloro-1,2,3,4-tetrahydroisoquinolinyl)]butyl}-8-azaspiro[5,4]decane-7,9-dione [ No CAS ]
  • 12
  • [ 3156-35-2 ]
  • [ 33537-99-4 ]
  • 13
  • [ 26011-71-2 ]
  • [ 33537-99-4 ]
  • 14
  • [ 33537-99-4 ]
  • adamantane-1-carboxylic acid [4-(6-chloro-3,4-dihydro-1<i>H</i>-isoquinolin-2-yl)-butyl]-amide [ No CAS ]
  • 15
  • [ 587-04-2 ]
  • 4-acetylbenzenesulfonyl-Rink resin [ No CAS ]
  • [ 33537-99-4 ]
  • 17
  • [ 104-88-1 ]
  • benzoquinone-(1.4)-bis-<2.5-diamino-anil> [ No CAS ]
  • [ 33537-99-4 ]
  • 18
  • [ 104-88-1 ]
  • KOH-solution [ No CAS ]
  • [ 33537-99-4 ]
  • 19
  • [ 54879-73-1 ]
  • [ 33537-99-4 ]
  • 22
  • 3-[2-(3-Chloro-phenyl)-ethyl]-hydroxymethyl-sulfamoyl}-propionic acid methyl ester [ No CAS ]
  • [ 33537-99-4 ]
YieldReaction ConditionsOperation in experiment
Elemental Analysis Found Carbon 58.1%, hydrogen 4.8%, nitrogen 10.6% (Calc. for C25H25ClN4O3S.0.25CH2Cl2 Carbon 58.5%, hydrogen 4.96%, nitrogen 10.8%). The 6-Chloro-1,2,3,4-tetrahydroisoquinoline may be prepared as follows:
  • 24
  • [ 108-95-2 ]
  • [ 33537-99-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide; In acetic acid; iii) Part of the product from ii) above (2.20 g, 6.8 mmol) was heated at 75 C. with phenol (2.25 g) and 45% w/w hydrobromic acid in glacial acetic acid (30 ml) for three hours. The reaction mixture was cooled to room temperature then poured onto a mixture of ice and dichloromethane. The aqueous layer was adjusted to pH 14 with 6N sodium hydroxide solution and extracted with dichloromethane (4*100 ml). The dichloromethane layers were combined then dried over magnesium sulphate, filtered and concentrated in vacuo. The crude product was subjected to chromatography (SiO2: 1-10% methanol/dichloromethane) to yield 6-chloro-1,2,3,4-tetrahydroisoquinoline as a colourless oil (558.1 mg); NMR Spectrum 2.66 (t, 2H), 2.88 (q, 2H), 3.78 (s, 2H), 6.98 to 7.13 (m, 3H, Ar H's); Mass Spectrum 168 (M+H)+.
  • 25
  • [ 33537-99-4 ]
  • 6-chloro-3,4-dihydroisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirring solution of 23 (1 mmol, 200mg) in dichloromethane and triethylamine15 (2mmol, 0.3ml) at room temperature was added N-bromosuccinimide (1.1rhmol,200mg). The reaction mixture was stirred at room temperature for 30min. Then2.0 M NaOH aqueous solution was added and the reaction mixture was stirred atrt for another 1 h. The reaction mixture as extracted with DCM. The combinedorganic layer was over MgS04 . The solvent was removed in vacuo. The crude20 product 24 was used in the next step without further purification
[0232] To a stirring solution of 23 (1 mmol, 200mg) in dichloromethane and triethylamine (2mmol, 0.3ml) at roomtemperature was added N-bromosuccinimide (1.1mmol, 200mg). The reaction mixture was stirred at room temperaturefor 30min. Then 2.0 M NaOH aqueous solution was added and the reaction mixture was stirred at rt for another 1 h. Thereaction mixture as extracted with DCM. The combined organic layer was over MgSO4. The solvent was removed invacuo. The crude product 24 was used in the next step without further purification.
  • 26
  • [ 33537-99-4 ]
  • C11H12ClNO2 [ No CAS ]
  • 27
  • [ 33537-99-4 ]
  • C12H14ClNO2 [ No CAS ]
  • 28
  • [ 33537-99-4 ]
  • C17H22ClNO4 [ No CAS ]
  • 29
  • [ 33537-99-4 ]
  • C16H20ClNO3 [ No CAS ]
  • 30
  • [ 33537-99-4 ]
  • [ 611-19-8 ]
  • [ 1552304-53-6 ]
YieldReaction ConditionsOperation in experiment
40% In acetonitrile; at 20℃; General procedure: 1,2,3,4-Tetrahydro-isoquinoline(1g, 7.5 mmol) was dissolved in 5 mL of anhydrous acetonitrile. Then to thissolution was slowly added 2-chloro- or 2-bromo-benzyl compound (7.5 mmol) and the reaction was carried out overnight at room temperature. The solvent wasremoved under reduced pressure. The residue was resuspended in 1 ml of DMSO andpurified using C18 flash chromatography as described above.
  • 31
  • [ 33537-99-4 ]
  • C20H26ClNO4 [ No CAS ]
  • 32
  • [ 33537-99-4 ]
  • C20H28ClNO4 [ No CAS ]
  • 33
  • [ 33537-99-4 ]
  • C15H20ClNO2*ClH [ No CAS ]
  • 34
  • [ 33537-99-4 ]
  • C36H38ClF6N3O5S [ No CAS ]
  • 35
  • [ 33537-99-4 ]
  • C34H34ClF6N3O5S [ No CAS ]
  • C34H34ClF6N3O5S [ No CAS ]
 

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Technical Information

Categories

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