185256-47-7|tert-Butyl ((1R,2S)-2-phenylcyclopropyl)carbamate| Ambeed

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Quality Control of [ 185256-47-7 ] Purity: 97% SDS Specification

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Product Details of [ 185256-47-7 ]

CAS No. :	185256-47-7
Formula :	C₁₄H₁₉NO₂
M.W :	233.31
SMILES Code :	O=C(OC(C)(C)C)N[C@H]1[C@H](C2=CC=CC=C2)C1
MDL No. :	MFCD21106315
InChI Key :	MBZAGPLGLMIZOL-NWDGAFQWSA-N
Pubchem ID :	15381986

Safety of [ 185256-47-7 ]

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

Computational Chemistry of [ 185256-47-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.5
Num. rotatable bonds	5
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	67.46
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.99
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.82
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.07
Log P_o/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.	2.53
Log P_o/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	2.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.99
Solubility	0.236 mg/ml ; 0.00101 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.	-3.28
Solubility	0.122 mg/ml ; 0.000522 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	-3.72
Solubility	0.044 mg/ml ; 0.000189 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	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.	-5.72 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	0.0
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)	2.72

Application In Synthesis of [ 185256-47-7 ]

* 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 [ 185256-47-7 ]

[ 185256-47-7 ] Synthesis Path-Downstream 1~22

1
[ 3471-10-1 ]
[ 185256-47-7 ]
(-)-(1R,2S)-trans (2-phenyl-cyclopropyl)-carbamoyl azide [ No CAS ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.

2
[ 185256-47-7 ]
[ 95-62-5 ]

Yield	Reaction Conditions	Operation in experiment
3.6 g	With hydrogenchloride; water; In methanol; at 20℃; for 5.0h;	[0258] Into a 250-mL round-bottom flask, was placed tert-butyl (lR,2S)-2- phenylcyclopropylcarbamate (5.2 g, 22.29 mmol, 1.00 equiv), hydrochloric acid (100 mL, 4 N) in methanol (100 mL). The resulting solution was stirred for 5 hours at room temperature. The resulting mixture was concentrated under vacuum. This resulted in 3.6 g of (lR,2S)-2- phenylcyclopropanamine as a yellow solid. XH-NMR (300 MHz, CDC13): delta ppm: 7.32-7.20 (m, 3H), 7.15-7.08 (m, 2H), 2.66-2.57 (m, 1H), 1.93-1.88 (m, 1H), 1.70-1.62 (m 1H), 1.43- 1.37(m, 1H).

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[2]Patent: WO2014/164867,2014,A1 .Location in patent: Paragraph 0258.

3
[ 3471-10-1 ]
[ 75-65-0 ]
[ 185256-47-7 ]
(-)-(1R,2S)-trans (2-phenyl-cyclopropyl)-carbamoyl azide [ No CAS ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.

4
[ 185256-47-7 ]
[ 1986-47-6 ]

References: [1]Synthetic Communications,1999,vol. 29,p. 567 - 572.
[2]Journal of the American Chemical Society,2010,vol. 132,p. 6827 - 6833.

5
trans-2-phenylcyclopropane-1-carbazide [ No CAS ]
[ 75-65-0 ]
[ 185256-47-7 ]

References: [1]Synthetic Communications,1999,vol. 29,p. 567 - 572.

6
[ 23020-15-7 ]
[ 185256-47-7 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[2]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.

7
[ 97-71-2 ]
[ 185256-47-7 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[2]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.

8
[ 97-71-2 ]
[ 185256-47-7 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[2]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.

9
[ 946-39-4 ]
[ 185256-47-7 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[2]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[3]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[4]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[5]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.
[6]Tetrahedron Asymmetry,1996,vol. 7,p. 3505 - 3512.

10
((1SR,2RS)-tert-butyl-2-phenylcyclopropyl)carbamate [ No CAS ]
[ 185256-47-7 ]
[ 185256-49-9 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 6827 - 6833.

11
[ 3471-10-1 ]
[ 75-65-0 ]
[ 185256-47-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With diphenyl phosphoryl azide; triethylamine; at 90℃; for 5.0h;	[0257] Into a 250-mL round-bottom flask, was placed (lR,2R)-2- phenylcyclopropanecarboxylic acid 5 (5 g, 30.83 mmol, 1.00 equiv), tert-butanol (100 mL), diphenyl phosphorazidate "DPPA" (8.5 g, 30.89 mmol, 1.00 equiv), TEA (3.1 g, 30.64 mmol, 1.00 equiv). The resulting solution was stirred for 5 hours at 90C in an oil bath. After the reaction was completed, it was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1: 10). The collected fractions were combined and concentrated under vacuum. This resulted in 5.2 g (72%) of tert-butyl (lR,2S)-2-phenylcyclopropylcarbamate as a yellow solid.

References: [1]Patent: WO2014/164867,2014,A1 .Location in patent: Paragraph 0257.
[2]Chemistry Letters,2013,vol. 42,p. 1311 - 1313.

12
[ 185256-47-7 ]
[ 95-62-5 ]
[ 3721-28-6 ]

References: [1]Chemistry Letters,2013,vol. 42,p. 1311 - 1313.

13
[ 4407-36-7 ]
[ 185256-47-7 ]

References: [1]Chemistry Letters,2013,vol. 42,p. 1311 - 1313.

14
[ 110659-58-0 ]
[ 185256-47-7 ]

References: [1]Chemistry Letters,2013,vol. 42,p. 1311 - 1313.

15
[ 946-38-3 ]
[ 185256-47-7 ]