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Chemical Structure| 6914-79-0 Chemical Structure| 6914-79-0
Chemical Structure| 6914-79-0

1-Cyanocyclopropanecarboxylic acid

CAS No.: 6914-79-0

4.5 *For Research Use Only !

Cat. No.: A122118 Purity: 97%

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Product Details of [ 6914-79-0 ]

CAS No. :6914-79-0
Formula : C5H5NO2
M.W : 111.10
SMILES Code : OC(=O)C1(CC1)C#N
MDL No. :MFCD00190651
InChI Key :KSJJMSKNZVXAND-UHFFFAOYSA-N
Pubchem ID :2733259

Safety of [ 6914-79-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302+H312+H332-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Calculated chemistry of [ 6914-79-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 0.6
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 25.3
TPSA ?

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

61.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.72
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

0.02
Log Po/w (WLOGP)?

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

0.31
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.

-0.48
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

0.41
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.19

Water Solubility

Log S (ESOL):?

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

-0.48
Solubility 37.2 mg/ml ; 0.335 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.85
Solubility 15.5 mg/ml ; 0.14 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

-0.1
Solubility 88.9 mg/ml ; 0.8 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

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.

-6.96 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

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

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)

1.2

Application In Synthesis of [ 6914-79-0 ]

* 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 [ 6914-79-0 ]

[ 6914-79-0 ] Synthesis Path-Downstream   1~28

  • 2
  • [ 6914-79-0 ]
  • [ 598-10-7 ]
  • 3
  • [ 6914-79-0 ]
  • [ 88157-18-0 ]
  • 4
  • [ 6914-79-0 ]
  • [ 100-51-6 ]
  • [ 148332-48-3 ]
  • 5
  • [ 67-56-1 ]
  • [ 6914-79-0 ]
  • [ 6914-73-4 ]
  • 7
  • [ 6914-79-0 ]
  • aqueous KOH-solution [ No CAS ]
  • [ 598-10-7 ]
  • 9
  • [ 6914-79-0 ]
  • 1-trifluoromethyl-cyclopropanecarbonitrile [ No CAS ]
  • 10
  • [ 123-75-1 ]
  • [ 6914-79-0 ]
  • 1-[(1-cyanocyclopropyl)carbonyl]pyrrolidine [ No CAS ]
  • 11
  • [ 110-89-4 ]
  • [ 6914-79-0 ]
  • [ 546114-01-6 ]
  • 12
  • [ 110-91-8 ]
  • [ 6914-79-0 ]
  • 1-[(1-cyanocyclopropyl)carbonyl]morpholine [ No CAS ]
  • 13
  • [ 6914-79-0 ]
  • [ 139126-42-4 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In toluene; at 80℃; for 0.25h; The compound was prepared according to the procedure for Intermediate 3, starting from Intermediate 2 and 1-cyanocyclopropanecarbonyl chloride (generated in situ from 1- cyanocyclopropanecarboxylic acid and excess thionyl chloride in toluene at 800C for 15 min.). APCI-MS m/z: 576 [MH+].
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; Compound 1-238[00461] To a solution of l-cyanocyclopropanecarboxylic acid (10 equiv) in dichloromethane was added oxalyl chloride (9 equiv) and catalytic N,iV-dimethylformamide. Once gas evolution ceased, this crude reaction mixture was added portion- wise to a suspension of Compound 1-107 (1 equiv) in dichloromethane/pyridine (1 :1) until complete consumption of starting material was observed by LS/MS. Purification via washing residual solid with diethyl ether following an aqueous ammonium chloride and dichloromethane workup (and subsequent concentration of organics) provided the desired compound as a yellow solid (27percent).1H NMR (400 MHz, DMSO-i/6) 9.41 (s, IH), 9.09 (d, IH), 8.04 (s, IH), 7.53 (s, IH), 7.41- 7.30 (m, IH), 7.24 (d, IH), 7.24-7.20 (m, IH), 7.11 (t, IH), 7.03 (bs, IH), 6.86 (t, IH), 5.90 (s, 2H), 1.72-1.64 (m, 4H) ppm.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 2h; [00248] To a solution of 1-cyanocyclopropanecarboxylic acid (80 mg, 0.72 mmol) and oxalyl dichloride (136 mg, 1.08 mmol) in DCM (5 mL) was added a drop of DMF at 0 °C, then the mixture was stirred for 2 h, after completion the reaction mixture solution was used for next step directly.
  • 14
  • [ 6914-79-0 ]
  • C11H7N2OCl3 [ No CAS ]
  • 15
  • [ 6914-79-0 ]
  • C11H9N2OBr [ No CAS ]
  • 17
  • [ 6914-79-0 ]
  • 1-cyano-N-(2,4-dichlorophenyl)cyclopropanecarboxamide [ No CAS ]
  • 18
  • [ 6914-79-0 ]
  • C12H12N2O [ No CAS ]
  • 19
  • [ 6914-79-0 ]
  • C11H9N2OCl [ No CAS ]
  • 20
  • [ 6914-79-0 ]
  • C7H10N2O2 [ No CAS ]
  • 21
  • [ 6914-79-0 ]
  • C12H9F3N2O [ No CAS ]
  • 22
  • [ 6914-79-0 ]
  • C11H9N2OCl [ No CAS ]
  • 23
  • [ 6914-79-0 ]
  • C12H9F3N2O [ No CAS ]
  • 24
  • [ 6914-79-0 ]
  • C12H9N2OF3 [ No CAS ]
  • 25
  • [ 6914-79-0 ]
  • C12H12N2O2 [ No CAS ]
  • 26
  • [ 6914-79-0 ]
  • 1-cyano-N-p-tolylcyclopropanecarboxamide [ No CAS ]
  • 27
  • [ 6914-79-0 ]
  • 1-cyano-N-(4-bromophenyl)cyclopropanecarboxamide [ No CAS ]
 

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