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Structure of 6940-76-7

Chemical Structure| 6940-76-7

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Product Details of [ 6940-76-7 ]

CAS No. :6940-76-7
Formula : C3H6ClI
M.W : 204.44
SMILES Code : ICCCCl
MDL No. :MFCD00001096
InChI Key :SFOYQZYQTQDRIY-UHFFFAOYSA-N
Pubchem ID :81363

Safety of [ 6940-76-7 ]

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

Computational Chemistry of [ 6940-76-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 5
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 34.29
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.

1.83
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

2.28
Log Po/w (WLOGP)?

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

2.05
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.

2.6
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

2.19
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.19

Water Solubility

Log S (ESOL):?

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

-2.41
Solubility 0.792 mg/ml ; 0.00387 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.

-1.92
Solubility 2.47 mg/ml ; 0.0121 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

-2.67
Solubility 0.441 mg/ml ; 0.00216 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

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

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.

-5.93 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

2.0 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)

3.24

Application In Synthesis of [ 6940-76-7 ]

* 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 [ 6940-76-7 ]

[ 6940-76-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 6940-76-7 ]
  • [ 98968-72-0 ]
  • [ 121006-55-1 ]
  • 2
  • [ 6940-76-7 ]
  • [ 105228-46-4 ]
  • (3R,5R,6S)-3-(3-Chloro-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester [ No CAS ]
  • 3
  • [ 6940-76-7 ]
  • [ 70298-89-4 ]
  • [ 121006-60-8 ]
  • 4
  • [ 13781-53-8 ]
  • [ 6940-76-7 ]
  • 5-chloro-2-thiophen-3-yl-pentanenitrile [ No CAS ]
  • 5
  • [ 6940-76-7 ]
  • [ 326-62-5 ]
  • 5-chloro-2-(2-fluoro-phenyl)-pentanenitrile [ No CAS ]
  • 6
  • [ 110-91-8 ]
  • [ 6940-76-7 ]
  • [ 57616-74-7 ]
YieldReaction ConditionsOperation in experiment
32% A solution of morpholine (2 mL, 23.0 mmol) in /V,A/-dimethylformamide (15 mL) was treated with potassium carbonate (4.75g, 34.4 mmol) and1-chloro-3-iodopropane (3.7 mL, 34.4 mmol). After 16h, the reaction mixture was partitioned between EtOAc and H20. The aqueous layer was washed with EtOAc(15x). The combined organic layers were dried (Na2S04) and concentrated. 1H NMR indicated a very large amount of DMF still remaining, so the product was taken up in EtOAc and washed with H20. The organic layer was washed with brine, dried (Na2S04) and concentrated. The resulting pale yellow oil was taken up in Et20 and treated with 4N HCI in dioxane to precipitate the product, affording 1.45g (32%) of the hydrochloride salt of 4-(3-chloropropyl)morpholine as a white solid. 1H NMR (D20): 8 3.94 (br m, 2H), 3.70 (brm, 2H), 3.53 (m, 2H), 3.15 (brm, 2H), 3.19 (m, 2H), 3.10 (brm, 2H), 2.08 (m, 2H).
  • 7
  • [ 103260-44-2 ]
  • [ 6940-76-7 ]
  • [ 1123192-39-1 ]
YieldReaction ConditionsOperation in experiment
Synthesis of ethyl 5-chloro-2-(tetrahydropyran-4-yl)-valerate 672 mg of the title compound was obtained from ethyl (tetrahydropyran-4-yl)acetate (CAS No. 103260-44-2, 650 mg) and 1-chloro-3-iodopropane (0.61 ml) according to the method in Example 113. The property value of the compound is as follows. ESI-MS; m/z 249 [M++H].
  • 8
  • [ 6940-76-7 ]
  • [ 1027-35-6 ]
  • ethyl 3-(3-chloropropyl)-4-oxopyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine; In tetrahydrofuran; Embodiment 6 Preparation of 1-ethoxycarbonyl-4-(3-chloropropyl)-3-pyrrolidone <strong>[1027-35-6]1-benzyl-4-ethoxycarbonyl-3-pyrrolidone</strong> (2.5 g, 10.1 mmol) is dissolved in 25 ml tetrahydrofuran and then cooled by ice water bath, triethylamine (2 g, 20.2 mmol) is added and stirring is performed for 30 minutes, 1-chloro-3-iodopropane (4.12 g, 20.2 mmol) is dripped, this dripping is finished 30 minutes later, afterwards, the temperature is raised to room temperature for the purpose of continuous reaction for 18 hours. Extraction is carried out by methylene dichloride (10 ml*3 times) at the end of reaction, organic phase is combined and dried by anhydrous sodium sulfate, and the solvent is dried by concentration under reduced pressure to obtain oily product, which is then purified by column chromatography to obtain oily product (6-1) (2.12 g, 6.57 mmol, yield 65percent). 1H NMR (500 MHz, CDCl3) delta7.34-7.27 (m, 5H), 4.17 (q, J=7.1 Hz, 2H), 3.71 (s, 2H), 3.48-3.51 (m, 2H), 3.40 (d, J=9.6 Hz, 1H), 3.19 (d, J=17.2 Hz, 1H), 2.99 (d, J=17.2 Hz, 1H), 2.73 (d, J=9.6 Hz, 1H), 2.04-2.02 (m, 1H), 1.92-1.89 (m, 2H), 1.71-1.69 (m, 1H), 1.24 (t, J=7.1 Hz, 3H). MS-ESI: m/z: 324 (M++1).
  • 9
  • [ 6940-76-7 ]
  • [ 1027-35-6 ]
  • [ 1430075-12-9 ]
YieldReaction ConditionsOperation in experiment
65% <strong>[1027-35-6]1-benzyl-4-ethoxycarbonyl-3-pyrrolidone</strong> (2.5g, 10.1mmol) is dissolved in 25ml tetrahydrofuran and then cooled by ice water bath, triethylamine (2g, 20.2mmol) is added and stirring is performed for 30 minutes, 1-chloro-3-iodopropane (4.12g, 20.2mmol) is dripped, this dripping is finished 30 minutes later, afterwards, the temperature is raised to room temperature for the purpose of continuous reaction for 18 hours. Extraction is carried out by methylene dichloride (10ml × 3 times) at the end of reaction, organic phase is combined and dried by anhydrous sodium sulfate, and the solvent is dried by concentration under reduced pressure to obtain oily product, which is then purified by column chromatography to obtain oily product (6-1) (2.12g, 6.57mmol, yield 65percent). 1H NMR (500 MHz, CDCl3) delta7.34-7.27 (m, 5H), 4,17 (q, J = 7.1Hz, 2H), 3.71(s, 2H), 3.48-3.51(m, 2H), 3.40 (d, J = 9.6Hz ,1H), 3.19 (d, J = 17.2Hz,1H), 2.99 (d, J =17.2Hz,1H), 2.73 (d, J = 9.6Hz, 1H),2.04-2.02(m, 1H),1.92-1.89(m,2H),1.71-1.69(m, 1H),1.24(t, J = 7.1Hz, 3H). MS-ESI: m/z:324(M++1).
  • 10
  • [ 6940-76-7 ]
  • [ 15893-42-2 ]
  • 6-chloro-1-(4-methoxyphenyl)hexan-3-one [ No CAS ]
  • 11
  • [ 6940-76-7 ]
  • [ 6628-68-8 ]
  • diethyl 2-(3-chloropropyl)-2-phenethylmalonate [ No CAS ]
  • 12
  • [ 6940-76-7 ]
  • [ 34074-22-1 ]
  • 1,3-dichloro-2-(3-chloropropoxy)-5-iodobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.27 g With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 5h;Inert atmosphere; To a solution of 2,6-dichloro- 4-iodo-phenol (1) (1.0 g, 3.46 mmol) in DMF (20 mL) was added l-chloro-3-iodo-propane (2) (708 mg, 3.46 mmol) and CS2CO3 (2.26 g, 6.92 mmol) under N2 atmosphere at 20 C. The reaction was stirred at 60 C for 5 hours. TLC showed the reaction was completed. The solution was poured into H2O (20 mL), extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine (50 mL x 3), dried over NaiSOr. filtered and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography to give 1,3- dichloro-2-(3-chloropropoxy)-5-iodobenzene (80.0 %, 1.27 g, yield: 80.3 %) as brown oil. NMR(400MHz, CHCb-d) d 7.63 (s, 2H), 4.15 (t, .7=5.7 Hz, 2H), 3.85 (t, 7=6.4 Hz, 2H), 2.28 (t..7=6. 1 Hz. 2H).
 

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